What Now? The Uncertain Future Of Neo-Prep

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In light of the recent Boston Magazine article on Vineyard Vines, we revisit DCG’s first Millennial Fogey column, from November 2013.

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To speak of preppy-with-a-twist among trad purists is to garner reactions ranging from “What does this have to do with Ivy style?” to “Stop wasting my Internet, I want to look at old advertisements.”

But as much as Ivy stylers would like to forget it, the apparel industry does not operate within fixed genre parameters. There are gray areas, economic changes, and the ever-nebulous terminology used to describe things. It is hardly arguable, however, that fashion trends have at least some measurable effect on even the stodgiest of menswear merchants. From approximately 2004 to 2012, the fashion trend we can term “Neo-Prep” achieved remarkable mainstream popularity.

But will it last?

It may seem odd to attempt a history of less than a decade of a single fashion trend, but in the Information Age 10 years is an eternity. Some time at the dawn of the 21st century, this trend began possibly as a refutation of the relaxed nature of the ’90s, a rejection of the slovenly style of Silicon Valley, or a reaction against collegiate t-shirt culture (including those intrepid undergrads who wear flip-flops in January). Regardless of its origins, the aspirational wheels were in full motion by 2009.

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Gant, heyday shirtmaker for the Ivy League that has since evolved into a multinational European apparel brand, refocused much of its creative energies on its Rugger line designed with an eye towards ’60s Ivy League sportswear but cut aggressively slim and pre-weathered to appeal to the mass-marketed rebellious vibe embraced by millennials. Rugby Ralph Lauren, founded in 2004, was having remarkable success in branding itself as a “preppy with a twist” line for young adults anxious to set themselves apart from the masses by sporting a tie and a fake crest with their denim instead of an ironic t-shirt. The year 2009 was also the start of Tommy Hilfiger’s eventual resurrection from streetwear obscurity to preppy powerhouse. After years of logo saturation and brand trashing, the company slowly brought itself about. With giant steps forward, including a rejuvenated relationship with Macy’s and acquisition by Phillips Van-Heusen, in 2010 Women’s Wear Daily declared Tommy Hilfiger the “Master of Reinvention.”

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The Neo-Prep cultural moment seems to have reached its high-water mark from 2010 to 2011. Perhaps the most glaring example of the existence of this hipster fashion prep subset was 2010’s unlikely collaboration between J. Press and Urban Outfitters. Books published during these years included the re-released “Take Ivy”, “Hollywood and the Ivy League Look,” but more on point “Preppy: Cultivating Ivy Style” and Lisa Birnbach’s return to prepdom with “True Prep.” In the spring of 2011, Tommy Hilfiger’s namesake brand embarked on what was billed a “Prep World Tour,” setting up temporary shops in public spaces across the world’s capitals in miniature faux-New England cottages.


After some setbacks in various American locales, Rugby Ralph Lauren opened a store in London in the fall of 2011.  Neo-prep blogs, foremost among them Unabashedly Prep, reflected an active population of young adults interested in taking preppy staples and wearing them in ways that felt current, items of clothing that were steeped in heritage (not always fully appreciated or understood) worn alongside neon sneakers that would pass muster at any ecstasy-soaked Röyksopp (for the fogeys: a Norwegian electronic music duo) concert.

Speaking of music, the soundtrack to the Neo-Prep trend is inarguably Vampire Weekend. This group of Ivy Leaguers exploded on the music scene in 2007 and was downloaded immediately onto countless Neo-Prep iPhones to be blasted in the ZipCar whilst cruising towards Chatham on Route 6 or Sagaponack on the Montauk Highway. The bands first two albums are musically lighthearted with danceable, African-influenced rhythms, yet they also touch on very preppy problems, such as materialism and the WASP legacies of colonialism and sexual repression. There is also a song about vampires taking over Cape Cod, which is a less pressing preppy problem, but a catchy tune nonetheless.


It looked as though the second decade of the 21st century would continue to be dominated by twentysomethings listening to loud music in louder clothing, yet in 2013 Rugby was shuttered. The void was filled by the confusing Red Fleece line by Brooks Brothers, and York Street by J Press, which is less Rugby and more Thom Browne-style fashion forward rather than tweedpunk lifestyle. The novelty of überlayering has, shall we say, worn thin, and Neo-Prep outfits look terribly dated to this author. Tommy Hilfiger has subdued some of his louder outfits, and  Ralph Lauren is making far more money from Denim & Supply grungewear than it ever did from Rugby. Vampire Weekend’s latest album, “Modern Vampires of the City,” released three years after their previous project, is darker, more concerned with recent college graduates’ chronic unemployment than Louis Vuitton or coastal escapades.

True preppy style — clothing that could be described as Ivy style weekend wear — isn’t going anywhere. It will continue to influence fashion designers, to be used as a cultural marker for wealth, to be worn by those across the globe who appreciate it. However, the highly specific youth-driven fashions sold for the past few years (velvet slippers worn as street shoes, fake varsity patches, tweed vests worn with bow ties and distressed denim) have largely either disappeared from current mainstream stores, been adopted as streetwear by adolescents, or been drafted piecemeal into higher-end fashion lines at higher prices. It would seem that Neo-Prep has, for the time being, disintegrated.


If this trend has indeed run out of steam, if the Neo-Prep zeitgeist has truly run its short course, ultimately what may have doomed the upbeat movement is the decidedly downbeat spirit of this new decade. The same anxiety that spawns countless nightmares of nuclear cannibal apocalypse and has replaced the stylish vampire with the decaying ravenous zombie in films does not bode well for fun shirts and Converse sneakers.

Considering that 2012 was only last year, it’s a little soon to attempt a post-mortem. After all, this may be a mere lull in what might turn out to be an enduring trend. It also remains to be seen where the bulk of the young people that drove this trend end up, sartorially speaking. It’s very likely that the generation will simply move on to the next trend, whatever that may be. This is the usual course. Naturally a few will stay on, to be found wandering the halls of the Ralph Lauren, catching the elevator at 346 Madison, or pestering the salesmen at J Press. — DANIEL C. GREENWOOD

128 Comments on "What Now? The Uncertain Future Of Neo-Prep"

  1. Bravo and welcome aboard.

  2. Vampire Weekend formed at Columbia. Aside from that, great article!

  3. Very nice analysis, Mr. Greenwood. I concur with Fred’s assertion that the “neo-prep” – I like that, by the way – movement has at the least, exposed a generation to the importance of classic style and the foundations of East Coast/Ivy League fashion. Even though they may not appreciate the nuances and history of these style staples, the underlying balance and longevity of core wardrobe items like a great pair of khakis, the oxford cloth button down, a Shetland sweater, or a blue blazer, will likely be retained.

    Typically, I dislike lumping an entire population or market segment into a generic category – in effect commoditizing complex human beings for the purpose of easy illustration – but I think that you have effectively captured the overarching trend and its movement through both the marketplace and the cultural landscape.

    Nice job.

  4. Mr. Chensvold, I am curious as to where you would file Michael Bastian?

  5. Your writing and smug biography makes me miss Christian. Your point, however, is well-taken. I hope the awful nouveau-preppy thing goes away soon, but aside from the demise of Rugby, I don’t really see evidence of that happening.

    Real preppy clothes, by which I mean non-updated classics, that were designed for younger people (i.e., not made with 38 inch waists, swollen ankles, and moobs (on a good day) in mind) would be great, and probably successful if anyone would produce them. (I had hoped York Street would be this answer, but it’s definitely not.) Bill’s M1s are great if you enjoy pants that resemble a spinnaker in a light breeze. Bill’s M3s are great if you are a eunuch who wears a size 6 shoe. And Bill’s M2s split the baby in the worst possible way.

    cRc: I’m not Mr. Chensvold, but my opinion on Michael Bastian is this: He started out making a few fashion-y pieces (like the idiotic shorts with faux boxers showing through the hem), but always produced really solid basics with a good, grown-up fit and exceedingly high quality. (Khakis were legendary.) In fact at the time, he claimed he started the company because there wasn’t anything on the market that wasn’t super fashion-y or completely fuddy-duddy and style-less. Yet he was never very successful because the prices were insane due to production by Cuccinelli.

    Then he realized that he could cash in on #MENSWEAR by producing less expensive, trendier clothing with an awful fit (8 inch rises don’t work on men who someday hope to reproduce and also need to tuck in a shirt occasionally!) and inferior quality. And if people are moving on, as this article claims, then soon his company won’t exist anymore.

  6. Nicely done. What may be missing is a dive into the psychological septic tank which drives/drove this trend. It’s always shocked and irritated me when people/hordes co-opt a style regardless of the nuances, realities and experiences of their own, actual lives. This is especially acute with ‘neo prep’ given the societal and perceived economic markers associated with it, but similarly odd behavior can be seen in many other style trends: surf wear, skater wear, grunge, goth, western wear, workwear, and so on.

    To me, clothes are primarily about practicality – clothes that work within and compliment one’s natural, honest day to day life. Individual style – beyond the clothes – should develop naturally as an extension of this. Neo prep is about clothes as aspirational dress up; clothes as purposeful costume….with all the forced starts and stops, revisions, and ignorance that come with these sorts of trends. This is strange, delusional, desperate, needlessly expensive, ironic, many times hypocritical, and laughably predictable and transparent.

  7. …has anyone ever dropped E at a Royksopp concert? It seems incongruent as hell.

  8. This was one of the last interesting articles on Prep I read, enjoy it.


  9. emjkmj: Unfortunately, the author of that article, Will Welch, dresses like this now: http://www.gq.com/style/blogs/the-gq-eye/2011/12/office-style-will-welchs-all-black-everything.html . His criticism of those who adopted preppy as a trend back in 2009 should probably be tempered by the knowledge that he was, apparently, one of them.

  10. That GQ article is spot on.

  11. fred astaire | November 21, 2013 at 3:01 pm |

    Well done article.

    Fashion is a gimmick. In order to make money, “you gotta have a gimmick” and stay front and center in the public eye. With only so many options out there clothing designers and manufacturers rehash “with a twist” those ideas and products that have been wrung out in the past.

    I don’t believe there is any harm in it. Hell, it’s capitalism! It’s the same with car redesigns and granite counter tops and stainless steel appliances–the avocado and harvest gold of today–find a gimmick and sell the hell out of it to the masses. Pet rock anyone?

  12. @madaket Smug? Well, I suppose I can trace my ancestry back to a protoplasmal primordial atomic globule…

    The writing however, is inexcusable, I agree!

  13. I find it strange that your personal biography would include information about what other people, who are not you, have done. Any yes, the implication–that including such information is relevant because it bestows upon you some credential–is smug. Most people who weren’t raised in a barn consider public discussions of pedigree rude.

    Congrats on being related to people who used to own a business and once attended prestigious schools, though.

  14. @madaket – how does using a Nantucket beach name as your handle fit into your last criticisms?

  15. @madaket I’m proud of my family’s accomplishments and have seen firsthand the damage that fast fashion does to American manufacturing. Apologies if that comes off as smug.

    @AEV I was wondering what you’d think of this, for all the online back and forth I believe the core of what disturbs you about these trends is the same as what disturbs me. It’s commodification of a culture, never a pretty thing.

  16. AEV: like, not at all? I choose not to use my name or initials when commenting online, my dog’s name is strange, and it was something that came to mind as a place that I like a lot. You must be a terribly sensitive boy if you’re offended by the barest whiff of pomposity implied by my handle: that I have, at some point, been to Nantucket.

    I’m thrilled to hear your explanation of how using a favorite place as a screen name is comparable to talking about the irrelevant accomplishments of unnamed dead people for 50% of a three-line autobiography, though.

  17. I’ve heard people called smug for talking too much about themselves, but never for talking too little!

  18. @madaket –

    Simple: you took issue with someone referencing their family’s business and links to the Ivy League, suggesting it was rude to discuss pedigree or suggest Ivy League/clothing industry references as veiled credentials.

    Using a Nantucket beach name as your handle – especially on an ‘Ivy style’ blog – attempts to telegraph the exact same things.

    I hope that’s clear enough.

  19. I guess I just feel badly for you that out of the three sentences you wrote to introduce yourself and your qualifications to your readers, you thought the most relevant information to include was about other people. Have you your own qualifications for writing on this subject? We wouldn’t know, only that you are a musician and purported writer living in NYC. Family history is great and all, but if it’s your defining characteristic, you’re in deep trouble.

  20. AEV: You’re really stretching here, but I admire your dedication to trying to proving yourself right. It’s nothing alike, and I’m sure you really know that, deep down. “Madaket” implies that I like a particular place on Nantucket that is renowned for its natural beauty. It says nothing overt or tacit about my supposed pedigree.

    Question: If I asked you to write a short bio of yourself, would you leave out where you attended school and include where your unnamed relatives went?

  21. @madaket – Uh huh.

    For all we know, given how vague the ‘bio’ is, the author himself attended an Ivy League school. Maybe he even has a house in Madaket – you know, because he appreciates its natural beauty.

    It’s pretty clear to me that he’s making the Ivy reference in recognition of the blog he’s writing on/for.

  22. @madaket – I think because this is a blog called ‘Ivy-Style’, there is no reason to berate someone who happens to mention his pedigree here. his short bio adds insight into exactly where his point of view is coming from. First he tells us his name and occupation. Then he goes on to tell us what his family’s business has been, and that directly relates to much of the topics on Ivy-Style. Finally, he gives us the information that he went to an Ivy League and wore Brooks Brothers, once again on topic with this blog’s overall theme. That short bio establishes his value and credibility in writing on the subject.

    If I wrote this article, what value would it have? Much less than DCG, if at all any value. If DCG did not give us a background, we might just assume it’s a random collection of thoughts from Christian. So in the end, it’s nice to know who DCG is, and what he has developed an appreciation for, through exposure in his family’s business and attending an Ivy Leagu.

  23. A quick Google reveals the author didn’t go to an Ivy, which you would have guessed if you possessed basic critical thinking abilities–no one so pretentious as to make vague mention to relatives’ Ivy League cred in their bio would be so humble as to leave out their own, if it existed.

    So, AEV, to repeat the question: you wouldn’t include where you attended school in your own biography, while including where unnamed relatives went?

  24. Again, it’s pretty clear to me that he’s making the Ivy reference in recognition of the blog he’s writing on/for. It’s also clear that it’s more of a bi line/footer than it is a comprehensive biography…..

    Just like it’s pretty clear to me that you’re making the Mataket reference because you believe that it telegraphs to people a signal of affluence, exclusivity, ‘preppiness’, or some combination of the three.

    Fine (albeit irritating), I suppose, but not if you’re going to throw stones at the author for the exact same perceived transgressions.

  25. A.E.W. Mason | November 21, 2013 at 5:02 pm |

    Very well done and interesting. Being at the point of “advanced” middle age it’s a bit beyond me. However, anything that will get young adults to dress with some care and avoid ventilated footwear is alright by me.

    Again, thank you for a most interesting piece.

  26. Too true, too true, I did not go to an Ivy League school! I attended humble Ithaca College for my musical education. I appreciate the fact-checking. However, many of my cousins, uncles, and forefathers attended, specifically, the University of Pennsylvania. They influenced me, and I stand on the sartorial shoulders of giants and give tribute for the development of my tastes where it is deserved.

    It seems like I’ve hit a nerve…let me assure you that I’m proud of my own accomplishments, they’re just not germane to this discussion. If you’d like me to write a detailed biography touting myself, I’ll ship you a copy when I publish it.

  27. Your accomplishments are not germane to your bio? That’s quite honest. Congratulations to your cousins, uncles, and “forefathers”, though. I’m sure they would be thrilled that the school they attended has had such a strong influence on your identity.

    Anyway, now that everyone has become further entrenched in their respective positions it’s probably time for me to terminate my end of this conversation and allow others to discuss the substantive issues raised in your piece, which are much more interesting.

  28. An amended bio:

    DCG aced Italian one time at Ithaca College and is entirely too obsessed with his grandfather’s prestigious education and career. He has no reason to write this article other than CC generously asked him to. He has also been to Nantucket on numerous occasions and is thus extremely impressive.

  29. For a guy who tells me he’s so reluctant to talk about himself….

    The Internet — it brings the Mr. Hyde out in all of us.

  30. Fred astaire | November 21, 2013 at 6:40 pm |

    WTF??? If you don’t like the blog or the author the go effing somewhere else! This isn’t about effing curing cancer! Sheesh!

  31. Where are (were) these 20 somethings who dress(ed) this way? In the past decade I have lived in Colorado, Vermont, and Wisconsin and I have not seen any neo-prep style outside of catalogs and the internet.

  32. Wait… so… should I keep ordering from J. Press or not? Someone tell me what to do.

  33. @JGH

    You won’t see people dressed neo-preppy much in the midwest, unless you go to a major collegetown. I would imagine NY and DC are where most are from, at least in the East coast. I guess wherever You can find me is also a good spot to check, you could call me neo-prep, I won’t take offense, but I admire Ivy style and the history behind everything involved.

    I would guess AEV would refer to me as one of those who might dress (neo)preppy because of the aspirational aspect of why someone would, and i understand that. The style is definetly feigning the fact that the person wearing it is wealthy, smart or maybe even of a better class of people. Truth is, I am just now, in my mid 20s, beginning to apppreciate what my father has been banging into my head all of my life, like the reason why he prefers Weejuns, or why he buys sport coats from Brooks Brothers. I’ve always been interested and I would try on his blazers and sweaters as a kid, but until more recently there have not been more modern silhouettes that paid homage to the preppy/ivy style. People have always referred to me as preppy, but i never really understood why since I am a first generation American (parents immigrated here), I went to a private school where uniforms were required – but it wasn’t a preppy boarding school, and I did not go to a preppy/ivy college. I just sort of embraced it on my own, possibly false, way.

    Just thought I’d give you guys a perspective on the journey of a self confessed ‘neo’-prep, or at least I think I should be classified as a ‘neo’-prep


    Sorry I inferred from DCG’s bio more than I should have, I gave benefit of the doubt when he mentioned “that paid for many Ivy League tuitions” to also include his own. I think my point is still partially valid as to his background being suitable to speak to this topic.

  34. Orgastic future | November 22, 2013 at 1:44 am |

    Ivy, trad, preppy, neo-prep, post-neo prep(just coined it) are all costumes if following a set tradition of why, when, where and how to wear it based off of previous generations. However, if you simply are attracted to the style/lifestyle, then one should be able to wear it without a bunch of old headmaster wannabes denouncing their “pedigrees.” Even in it’s most unoriginal form, neo prepsters are still eons more original than generations of OCBD robots trying to clone grandpa’s closet. And good pull on the new “Vampy “Weeks” album….but it’s wonderful.

  35. I always wonder what the backstory for some of these contrived models are. I get the whole mix-and-match formality of taking off your tie and shoes when you get home from work, realizing you’re out of baked beans, and throwing on a Squall Jacket, a pair of moccasins, and an old bucket hat over the remnants of your work clothes to head to the store.

    But how do we get guys like Mr. Orange Vest?

    “So I came home from work and immediately decided that I wanted a quickie with the Missus. So off comes the suit (no time for the shirt and tie), and we’re making good progress, but wow is it cold!

    ‘What’s the matter, honey?’

    ‘It’s just a little chilly in here…’

    ‘Well, why don’t you put on those Christmas socks your mother sent you?’

    Problem solved! We’re going at it again, and…

    ‘Did you remember to get the milk?’

    The milk! I forgot the milk! Well, no worries, I can just drive to the store when we’re through…

    ‘I’ll drive to the store later.’

    ‘It’s at the shop getting the brakes looked at, remember?’

    ‘Well, true… I can go pick it up at the corner store.’

    ‘You’d best do it now, then — they close in 15 minutes.’

    Dammit! OK, grab some pants, uh… these stupid ones from the party on Saturday are still clean..

    ‘Are you going out like that? It’s freezing outside!’

    ‘I’ll just wear the jacket on the hook.’

    ‘That jacket is camouflage! You’ll be hit by a car. ‘

    ‘Fine fine, I’ll put on the vest too…’

    ‘And wear some good boots so you don’t slip in the snow. And roll down those sleeves! You’re not gutting fish, you know.’

    ‘Yeah yeah, I’ll be right back.’

    ‘And some gloves, don’t forget gloves. I hate cold hands.’

    (Moments later…)

    Christ it’s bright in here! How many lights do they need? This is really making my stress headache worse. Well, maybe I’ll just…


    ‘Did you just photograph me?’

    ‘Well, I run a blog, you see…'”

  36. “The same anxiety that spawns countless nightmares of nuclear cannibal apocalypse and has replaced the stylish vampire with the decaying ravenous zombie in films does not bode well for fun shirts and Converse sneakers.”

    This is one of those sentences that is a lot more fun to write than it is to read. Nicely written otherwise.

  37. AEV said, “It’s always shocked and irritated me when people/hordes co-opt a style regardless of the nuances, realities and experiences of their own, actual lives.”

    I think that you are describing the American Dream. It is the ability to become what & who you want to be that has drawn people to this country. Even the oldest money was made at some point. Change is not a bad thing especially if it is actually growth. There is nothing wrong with aspiration. Just my humble opinion.

  38. Good article and a perfectly appropriate byline. I think castleberry may be our canary in this particular coal mine. Just as fred chased the surfer fashion fad and then latched on to aping prep fashion, he will certainly sniff out whatever the next new thing is and mimic accordingly. I’ve been trying to put my finger on why this neo prep nonsense irritates me so much. In part it is the shameless co-opting and absurd “re-invention” of the prep aesthetic. But I think my personal issue runs deeper. Growing up neither I nor my friends ever characterized ourselves as preppy. With the exception of TOPH the word never entered our conversations. Nor did we put inordinate thought into what we wore or what we ate or who we listened to or where we vacationed. We just were. It wasn’t until I went to college and was exposed to a more diverse (and wonderful) world that I began to understand the preppy culture I had grown up in (as seen through the eyes of others) and just how insular a community it was. I was a lifer at a well known prep school in the 70’s and early 80’s and there was very little ethnic or religious diversity. I went on to a New England liberal arts college and as I was exposed to the broader world I realized how shameful much of our behavior had been….this was far before the era of political correctness. The manner in which we casually tossed around negative stereotypes or aggressively poked fun at any student that strayed too far from the norm. I remember a new student entered in 9th grade and he was so foreign to us that we couldn’t really understand anything about him…his personal interests, the way he spoke, the way he dressed. It wasn’t until college that I realized he was what people referred to as a JAP…but what did we know….he was just different. I guess my point is that to truly understand prep culture and by extension fashion, I think you had to live through the experience. And it wasn’t all positive by any means….certainly not the caricature that the Muffy Aldrichs portray it to be.

  39. @oxford cloth –

    So, let’s say that I – with no previous experience or background – aspired to be a cowboy (you can also insert skateboarder, surfer, blacksmith, professional baseball player, chef, etc.). Would it not grate real cowboys (and the public in general) if I, one day, woke up and began dressing head to toe in modern, reinterpreted cowboy/western gear? Would that simply be a normal, everyday expression of the American Dream?

    With modern day, trendy neo prep (as described and referenced in this post) we’re not talking about naturally “becoming” and “changing” based on the realization of one’s dreams or aspirations. I have no problem with aspiration. I do have a problem with blatant copy catting, dressing in contrived costumes, a total lack of self awareness, and overt posturing.

  40. @Gornegrat –

    Well said. I agree completely and grew up similarly…..

  41. I forgot that we were discussing neo-prep and not prep. I was not talking about dressing like anything, but a respectable adult male. Neo-preps are fashion chasers so they chase fashion which at some point will include skateboarder, surfer, blacksmith, professional baseball player, chef. I could absolutely care less what clothing other people wear.

  42. @Dan Agreed…ah well too late now

  43. @AEV

    The uniform of the cowboy or baseball player speaks to specific occupations still happening in this day and age. Wearing a blazer and boat shoes no longer secretly signifies “old money” in the year 2013. That cat got let out of the bag years ago thanks to Ralph Lauren, TOPH, etc. OCBD’s, Weejuns, khakis – these are now just clothes the way basketball sneakers are now just shoes. They have a history and once served a particular function but became culturally absorbed. If wearing a bow tie gives you the confidence to go out and earn more money or whatever – more power to you. But I doubt anyone wearing pieces that can now be bought at JCP gives others the impression they have a yacht moored somewhere.

  44. I always enjoy reading different commenters’ take on Ivy / Collegiate / Trad / Soft Shoulder / Preppy style. Most of these opinions are based on parochial experience, no surprise. In the sixties Kansas City, preps were guys that went to prep schools, they dressed like most middle class high school students. We all shopped at the same stores, Mister Guy, Harold’s, Woody’s, Wolf Bros. Collegiate Shop, The Club Shop at Jack Henry’s and BB’s trunk sales at the Muehlebach Hotel. “Preppy” surfaced in the 1980s as a descriptive of the style, most of us, now in our mid 30s, were insulted by the term.

  45. @Halby –

    It’s not 100% the same, but it’s darn close. You can just easily substitute “cowboy” (a specific occupation of sorts) with ‘western wear’, a more general style and trend that has been assumed, mostly awkwardly, by many non-cowboys (including, years back, by Mr. Ralph Lauren himself…)….

    Again, I’m not talking about people wearing traditional staples. I – and this post – is speaking specifically to the neo-prep trend, which is obviously not just about wearing a bow tie for a confidence boost. The pics and blogs referenced in this very post prove that….

  46. I was 17 in 1963. Back then, and before, in the ’50s, the prevailing style for students at ANY college was mostly called “collegiate” or, to a slightly lesser extent, “Ivy League.” (The term “preppy” wasn’t used.) Take a look at a yearbook from any college in the ’50s and early-to-mid ’60s and you will see students wearing crew-neck Shetland sweaters, khakis (pleated skirts for women), button-downs, Madras shorts and shirts and Weejuns, bucks or saddle shoes, etc. It wasn’t a matter of class, background, the school one attended, or credentials of some sort. It was just what everybody wore, in a rather unself-conscious way.

  47. Yes, Dick, though those items and that national collegiate uniform came from somewhere. I don’t think it was nearly as prevalent nationwide before the war, yet would have been found on eastern campuses, particularly the ones known for setting styles.

  48. Does neo-prep cover the regional variations as well? Down South, we have a lot of prepnecks. Guys who wear Brooks Brothers or Billy Reid and unironic camo.

  49. You are right, Christian. In the ’50s, collegiate style and new variations largely originated at the Eastern colleges, particularly the Ivy schools. I remember sometime in the ’50s a new boy arrived in our neighborhood wearing khakis with a buckle in the back. Before long, all the kids were wearing khakis with back buckles, and we referred to them as “Ivy League.” Before the war, I think, collegiate dress was based more on English styles–argyle sweaters and socks, plus-fours, tweeds, letter sweaters, flat caps. Watch any college movie from the ’30s and ’40s (and there are lots of them) and that’s what you’ll see.

  50. @MAC

    I too feel insulted when somebody describes my standard outfit of navy blazer, grey flannels, blue OCBD shirt, cordovan penny loafers, and regimental stripe tie as “preppy”.

  51. Nowadays college students dress “preppy” either because that’s the background they came from/how they were raised, i.e. prep school, or just because they want to stand out from the masses in sweatpants, hoodies, and Zuckerberg-esque pajamas and flip-flops.


    Growing up down South, I can also attest to the fact that the “prep neck” is real and alive. Many of my friends are “prep necks”. Though, it’s not a costume or affectation. It’s simply they environment they grew up with….the ability to effortlessly go from duck blind to debutant ball. They love hunting deer and wearing camo, but they also love seersucker, Brooks Brothers, and bow ties.

  52. @AEV

    “What may be missing is a dive into the psychological septic tank which drives/drove this trend.”

    Right, but you said that these folks wearing the “neo-prep” look are attaching some sort of aspirational significance to their outfits – as opposed to just wearing whatever the internet tells them to because it’s deemed the new hotness. Which I believe is really the case. According to Complex.com, goth is now the new look! I cannot wait for Unabashedly Goth. I have some Specimen records I’d like to sell.

  53. @Halby –

    Have you been to, for example, Unabashedly Prep?! You don’t believe Fred – and many others like him – is attaching aspirational significance to, and a yearning for some sort of social/economic transformation through, his new ‘prep’ style, lifestyle, and ‘expertise’? C’mon….the guy has whitewashed the first 29 years of his life (as a small town TX bible beater who dressed like an Aeropostale catalog model and flitted around the west with his band of aging alterna-friends – google Mammoth Men and get ready for a ride)…..and now tweets/blogs/facebooks/instagrams/vines/and pinterests about palm beach, nantucket, new england, the ivy leage, $600 loafers, bmws, $350 jeans, and so on. And, while Fred is easy to pick on because of the grotesque hyperbole of it all, there are lots of people out there just like him (and how admire and copy him)….

    People like Fred who reinvent themelves, nearly completely from an external standpoint, overnight (from, in his case, JV emo-surfer in Abercrombie to Rugby mannequin in shell cordovan sleds) aren’t doing so because the internet told them prep was hot. They’re doing so for terrifying, shallow psychological reasons…..much of which I’ve already described.

  54. Ah yes, more demonstrably false claims that the word preppy is recent.

    Anyway, I don’t think anyone dressing in a neo-prep style is trying to appear as though they’re of any particular culture, whatever one wants to call that or define it, other than that they are into fashion. So those who somehow feel under siege by the existence of Gant Rugger or whatever can rest at ease.

    It sounds like a lot of people here want to define who can, and cannot, rightfully dress Ivy or preppy. That’s problematic for a variety of reasons, notably that the culture that defined that way of dressing simply doesn’t exist anymore. Northeastern WASPs who attended one of maybe ten, at most, New England boarding schools, and went on to a few top colleges or universities are basically nonexistant. The few, if any, who are extant are highly unlikely, in my personal experience, to dress preppy or Ivy or whatever we’re calling it. Anyone with a passing familiarity with the culture of the Northeastern elite institutions would know this, so the natural conclusion to draw is that those who want to impose conditions on dressing a certain way are themselves “not our kind” (which, for all intents and purposes, should be an extinct phrase).

  55. Good lord, AEV’s Fred posts are reaching their apex of inspired prose. Gentlemen, this is Henry James entering the masterly late phase.

  56. @madaket –

    I strongly disagree with a range of your assertions. I, for one, am not trying to decide who can dress like what. My simple, seemingly unarguable point, is that people should dress in an honest manner, one that is a reflection of their actual life and experiences – not, as is the case within much of the modern ‘prep’ world, in a costume-y way that simply copies and postures, attempting to signal and assume all sorts of things which simply aren’t real or accurate.

    Additionally, “prep”/Ivy/trad style is not simply or only derived from 10 northeastern prep schools, a handful of Ivies, or a bygone era of yankee aristrocracy and lineage. I grew up in and now live in CT and went to undergrad in Boston. The way I dress – and, in other ways, my ‘lifestyle’ – is derivative of a wide range of things: my schooling, familial schooling, family history, family values, the places I’ve lived, sports and hobbies, vacation spots, friends, family members, the weather, regional availability and branding, and so on. In other words, I dress in a way that reflects my life. Not in a way that mimics a catalogue, signals my aspirations, is meant to shock or draw attention, drives traffic to my blog or business, or expresses/exaggerates a current trend.

    Simple….and really, really easy.

  57. Orgastic Future | November 22, 2013 at 12:58 pm |


    I think you prefer America to be India’s Caste system. Sorry to inform you, but America is a free country, and we are free to choose our ways of life. If I wake up one day and want to be a soldier, surfer, skateboarder, rock star, professor, baker etc., who’s to stop me? The basis of your argument against FEC is that he decided to be what he wanted to be?????? Do you actually hear yourself?

  58. @ AEV – “JV emo-surfer”….that’s gold!

    @ madaket – you’re wrong. They exist.

  59. Nice article, but way too analytic for me. All I want to know is whether someone is going to remake the entire contents of the Brooks Brothers Autumn 1975 catalogue, at least in sizes that fit me, and keep the items in stock until I can pay for all of those I want to buy.

  60. @Orgastic Future –

    “Preppy” is not something one can wake up and decide to “be”. That’s the entire point. Dressing like something (e.g. a surfer, a Taft School senior from the mid-1980s) doesn’t make you that thing – it means you dressed up like that thing (like being Batman for Halloween).

    If you, Fred Egan Castleberry, or anyone aspire to ‘be preppy’, all I can do is chuckle. If, on the other hand, you aspire to move to the northeast and raise generations of Orgastic Catleberries who will naturally, slowly, organically wear the clothes and styles that come with a full life in New England, by all means…..start house hunting. You seem to be confused about what we’re actually discussing…..confusion, I’ve found, is a neo-prep hallmark.

  61. @CC – ….it’s more mid-career Kurt Vonnegut, Jr., but thank you.

  62. @AEV

    I think he’s just a dude trying to make money by jocking a particular trend? The internet has blown all these people’s covers, so trying to discredit photo evidence would be insanity. Fred never says that’s not him in those photos, he just never talks about his A&F past. If he did, yeah, that would be nuts.

  63. I guess the issue that you have is that fashion, for a time, has swept up a way of dressing that you, for whatever reason, have chosen to identify with. (Note that it is a choice to identify with preppy or Ivy style, regardless of whether your background imbues you with some perceived cred; those who know the few people who bear more than a couple of indicia of “authentic” affiliation with preppy/Ivy culture know that many choose to ignore the defunct sartorial shibboleths that once may have defined their class. And you could dress in a way that is “honest” to your lifestyle without ever wearing a Repp tie, I’d bet.) This happens, believe it or not, to all clothing styles that are distinctly associated with a particular class, culture, place, way of life, etc. I’m sure punks who were dressing in a way that reflected their life and belief system were annoyed by fashion in the 1980s, for example.

    And yet. And yet! It has absolutely no effect on you, at all. Unless you think you are going to be mistaken for a neo-prep fashionista, you really should have no concern. No one is pissing on your grandparents’ gravestone. You can still stand tall in your Quoddys over your inferiors in Sperrys, secure in the knowledge that your uncle went to Penn.

    You are, by the way, drawing lines about who can, and cannot, rightly dress a certain way. Your comment could be summarized as “Fred Castleberry can’t dress the way that he does because his way of dressing is untrue to his family history, lifestyle, etc”. In the context of this discussion, that essentially means: You can dress Ivy or preppy if you meet certain arbitrary conditions related to education, family history, and lifestyle that I have set. If not, you are dishonest. You may wear boat shoes if you have spent __ number of hours on a boat. You may wear Patagonia fleeces if you grew up skiing at __ resort. You may wear a J. Press blue blazer if your distant relative ___ attended Yale.

    In short, I think we can all agree that Fred sucks on the merits: he dresses embarrassingly badly. Whether he is entitled to wear a blue blazer with gold buttons is beside the point.

    Out of curiosity: How should Fred Castleberry dress? He is, apparently, a half-Asian Texan/California from a middle-class background living in New York City. Ten gallon hat, board shorts, hipster glasses and, I dunno, something Asian?

  64. @Halby –

    Fred, for one (to be clear, Fred is just one obvious, easy target amongst many), does indeed try to explain away his entire life pre-2009. One more than one occasion he has used all sorts of odd, defensive justifications for his style 180, including: he only dressed in flip flops and graphic t-shirts because he was trying to dress in a “CA style” to garner CA wedding photography business (laughable on its face, but also refuted by the dozens of photos of him in similar garb running around in TN, the SW, Vegas, etc. with his band of TX emo-alterna friends…), and that he actually did indeed grow up “preppy”, claiming he now paints his own clothes because it reminds him of painting his picket fence in TX and getting splatters all over his canvas sneakers. Right……just like he worked in “finance” before throwing it all away to be a freelance (wedding, high school, c-lister) photographer.

    Fred sure is trying to take full commercial advantage of a dying trend….but the psychological underpinnings, for him anyway, run much deeper.

  65. “You are what you pretend to be, so be careful about who you pretend to be.”

    ― Kurt Vonnegut, Mother Night

  66. @madaket – I’m not going to re-repeat myself. But, I would say that I’m discussing these issues/ideas within the confines of a specific, Ivy-themed blog. I’m not suggesting at all that Fred, or these concerns, have an outsized/measurable influence on my life….it is, essentially, a curiosity for me.

    How should Fred (or anyone) dress? I think I’ve been clear about this – but: in a way that naturally reflects one’s full life, not in a way that mimics a catalogue, signals aspirations, is meant to shock or draw attention, is intended to drive traffic to a blog or business, or expresses/exaggerates a current trend. For Fred, he’s been documeting his life online -shocker – for the better part of a decade….and for years he dressed in a way that seemed to reflect his actual life, his friends, his job, where he lived, where he vacationed, etc: like a JV emo-surfer. Terrible, but no worse – and far more believable – than his current costume.

  67. @anonymous – Sure is. So is this….all circa 2007-08:


  68. Beware of the man who works hard to learn something, learns it, and finds himself no wiser than before.
    -Kurt Vonnegut

  69. Sounds like golf.

  70. to be fair – the source on that last link is:


  71. @AEV

    “How should Fred (or anyone) dress? I think I’ve been clear about this – but: in a way that naturally reflects one’s full life”

    But his life is that of a blogger who blogs about preppy clothes and affectations? Are we through the looking glass yet?

  72. @Halby –

    No, his blog is obstensibly a reflection and documentation of his life – not his life unto itself.

    When asked, Fred does not claim to be a blogger. He claims to be a freelance photographer and designer (as he would also say, he’s a “creative”…like David Hockney or Slim Aarons. Really.)….his blog simply catalogues his life as those things (at least he believes it does). Interestingly, Fred was also a freelance photographer when these shots were taken: http://attachedphotography.com/blog/Fred%20Egan.jpg

    I don’t know what you looked like in 2008, but I can assure you that I dressed the same then as I do now.

  73. @AEV

    I dressed very poorly in 2008. I dress a bit better now. I sometimes dressed up like Batman when I was a kid. I’ll go buy a cape and cowl tonight. Just please don’t judge me.

  74. Most of my tradionally ‘preppy’ friends dress very poorly – nothing fits, everything’s worn, too much L.L. Bean, always the wrong shoes. Many of them have figured some of that stuff out as they’ve gotten older….but, no one would suggest that their styles or type of dress has changed.

    Dressing poorly is different and distinct from anything I was talking about.

  75. I’m with JGH on November 21. I don’t recall seeing anyone look like this where I live, our here in fly-over country. My daughter is a senior at a Big-10 school, and none of the kids have adopted this look: in hot weather it’s gym shorts and tees, in cold weather it’s sweatpants and hoodies.

    But I don’t mind anyone doing the neo-prep thing; a lot of people would look a lot nicer if they did.

    As Mao said, “Let a hundred flowers blossom.”

  76. I’d have to agree with @Halby on this one…and disagree with @AEV to an extent.

    Back in ’08 I dressed in graphic T-shirts, jeans and sneakers all the time. For some reason, I thought that was “cool”. I had no concept of style. I was still fairly young (and still am very young compared to most of the readers here). I never really paid attention to what I wore. Though around 2009…things changed. When I was at school and saw people in madras trousers, loafers, boat shoes, oxfords, bow ties, and khakis, I knew it was time to change. I wanted to fit in with the other “preppie” types (isn’t that what being “prep” is all about?). I started to read my father’s GQ magazines, and began asking him about his own personal style (finally realized that my father had a serious tassel loafer hoarding problem, and loved Ralph Lauren oxfords and chinos). He was proud that I started thinking/caring about how I dressed, and when I bought my first pair of boat shoes, he reminisced about his first pair.

    The way I had dressed before I was “style-conscious” had nothing to do with my “background”. I went to a private or “prep” school as my parents had, rowed on my school’s crew team, and now I currently attend university in Boston.

    My parents gave me the freedom to dress the way I wanted when I was younger. Same with the parents of most of the kids in my generation. Our fathers wear repp ties, tassel loafers, and navy blazers to work…some of us younger appreciate the style, and we wear it proudly. Others don’t. Many of my friends could be defined as “preppies” by the lifestyle they lead or how they were raised, but certainly don’t dress like it. Either because they don’t care, or as a form of rebellion.

  77. @madaket “Whether he is entitled to wear a blue blazer with gold buttons is beside the point.”

    Agreed, I think my biggest issue with “neo-prep” (a term I claim no credit for, I had originally used a way-too specific title) is that the clothing is too often worn just because it looks cool, not because it is appreciated for what it represents (its history, cultural significance, etc.)

    Who knows whether this is the fault of marketing teams, designers, bloggers, or consumers. It obviously bothers people here that think about these things, and I like that. Re: earlier, I do understand your point, didn’t intend to come off smug. Props for calling out my perceived “airs”, I also like that!

  78. Al, you must be misremembering your life. Rowing and having parents who went to prestigious schools naturally imbues you with the genetic material necessary to wear wide-wale corduroys properly. And your lifestyle of attending school and rowing a boat could only be facilitated by wearing khakis and OCBDs. Perhaps you were just being dishonest with yourself then. Perhaps your friends and colleagues were whispering: “Why is he wearing a tee shirt? He is an affluent white person in New England, attending a private school, and participating in a traditionally preppy sport! How strange.”

    Just ask AEV. The rigors of working in an office building in Connecticut require the high performance adaptability of a repp tie. Nothing else could suffice. Function over form!

  79. DCG: I certainly hadn’t intended to incite a drawn-out conversation about the merits of your bio with my snippy comment. But then, I have always had trouble turning down a completely petty debate, even in the fact of much more interesting matters to discuss.

  80. @madaket

    Nice one! I always enjoy a good dose of humor as a break from these overly-serious comments. God forbid that anyone would wear non-prep attire at prep school. It’s just not done!

    In all fairness, I grew up in the South, and just recently moved to New England. My family is originally from New York City…and, my grandparents are immigrants (how un-preppy!). I’m hispanic. What it ultimately boils down to is…no one really cares what you’re wearing but you. The main reason I decided to dress more respectably was because I enjoyed the look.

  81. Way too many comments about Fred. Not enough about Hilfiger or Rugby, or Neo-Prep. If it weren’t for Neo-prep, I don’t think the PITA revival would have been as strong as it’s been. And if there was no Neo-prep, we certainly wouldn’t be sweatin’ details such as natural shoulders, hook vents, and 3/2 rolls.

    I think having Neo-prep retailers around is not a bad thing. Perhaps the kids will form good roots and want to dress like the big boys and girls in a few years.

    Now, I think the Hilfiger campaign is an abomination. I’d like to punch everyone in that photo. But Rugby has a good place in Neo-prep. Tweed, college campus, the only girls have long hair… Also, the people behind Rugby were visible. Lee Norwood and John Fiske; they dressed like a Rugby kid’s Dad. It didn’t seem too forced, like Hilfiger’s version of prep, which is gross.

    Also, follow https://twitter.com/fecastelberry and thank me later.

  82. @AEV, did you hack Fred’s twitter account?

  83. @madaket –

    You’re willfully misunderstanding my point….and, it’s fairly obvious by now why. But, I never suggested that everyone who went to prep school or grew up in a certain area (e.g. the northeast) should, does, or ever did dress exactly the same. I just never said or suggested that. I explained how and why my style developed the way it did – that was all.

    As for @Al, it simply sounds like you’ve always dressed in a manner that you believed was cool, trendy, or would best allow you to fit in. In 2008, that was graphic t shirts and sneakers. Then, as you realized that dressing like that no longer allowed you to fit in, you changed your style (just like Fred!). (“Caring” how you dress doesn’t have anything to do with the style you’ve adopted or if your wear loafers vs. sneakers. Jay-Z’s sneakers cost more than my loafers and I’m guessing he and his stylists care a lot more what he looks like than I or you do…) . If dressing like that feels right to you – great. That’s not how I dress or approach my life….and, if you think no one cares what you’re wearing but you, you’re living an especially naive life. Enviable, perhaps, but naive.

    You and @madaket should trade email addresses and enjoy the natural beauty of Nantucket together…..lots of other people trying to fit in and be cool will inevitably be mingling with you on the beach. Be sure to tweet about it. And instagram about it. Take a few videos too. Maybe, even, start a blog.

  84. @emjkmj – No. But, whoever did deserves a round of drinks.

    I also don’t believe his account has been hacked….i think someone simply set up a parallel, parody account. For me, it’s hard to discern between the two.

  85. OMG, it is a parody account… Like the GS Elevator of neo-prep.

  86. Aspiration is well and good, but until you actually achieve something you may viewed as a poseur. That is just the way it works.

  87. @AEV…

    Well at least you didn’t call me an imposter. And by no means is wearing traditionally-fitting Brooks Brothers trendy. At least with people in my age group. In fact, my senior year of high school, most of the true “preps” had graduated. Vans or keds with our uniform oxfords, repp ties, and khakis became the new “cool” or “trendy” thing to wear. Though I stayed the same. I grew up and didn’t care what was “cool” or what wasn’t. Honestly, it’s not that I didn’t fit in before, I just liked the idea of dressing like an adult. People take you more seriously as a result.

    I believe due to the quite evident generational gap between us, we don’t tend to see eye to eye on these matters. I support neo-prep in a way because it helps my generation turn kids to good clothing choices in adulthood.
    Also, I already have a blog.

  88. What is “fairly obvious by now” about me poking holes in your silly List of People Who Can Wear Three-Two Roll Blazers? Was that a catty, queeny little burn about your perception of my preppy cred, or lack thereof? If so, three snaps, sister–that was a burn!

    The problem is, if I attempt to refute the implication, I’d be talking about pedigree which as I have mentioned is (1) rude and (2) irrelevant. Your little dig (if that’s not the implication of your passive aggressively vague comment, please elaborate!) also furthers my point that you believe that only people who meet criteria you set can dress in a style that you like.

    Those criteria are: (1) Be AEV. Criterium, then.

    Al: I’m pretty sure what AEV meant to say in his comment is that he would feel more comfortable if you just wore a sarape-patterned poncho. That would be honest, since you’re Hispanic and all. Clearly, there was some defect in your lineage for which you were punished by God (who is actually AEV) with wearing tee shirts and jeans in high school. If you were born into the right family, you would have had a closet full of sack suits to row crew in.

    Unfortunately for you, AEV–who you should know wore tartan diapers as an infant and attended boarding daycare–is not a forgiving God, and no matter how many LL Bean boat totes you own, this sin will never be forgotten. Give up. If you weren’t wearing natural-shouldered seersucker suits at 6 months, you will never achieve “honesty”.

  89. @madaket –

    Are you kidding me? What is possibly cotroversial – never mind bigoted – about suggesting that people should dress in a manner that naturally reflects their lives, experiences, upbringing, and background? Why does this bother you? How is this somehow less ‘personal’, less honest, or less authentic than, as Al and you have suggested, dressing in manner which you believe to be cool and will best allow you to fit in?

    You desperately want to turn this into some sort of socio-economic class battle. It’s not. Playing dress up in preppy clothes, under the auspices of ‘caring more’ or ‘wanting to fit in’, (or being a preppy blogger come pundit), or magically, suddenly loving critter pants, madras, tweed, and boat shoes all at once, is hardly reflective of some sort of aspirational, American dream realizing, Horatio Alger meritocracy. It’s playing pretend and dressing like a catalog/mannequin because you either lack your own innate sense of style or becaue you want to look like something you believe makes you, as Al so clearly stated, look cool and fit in. If it’s honest, you can look just as ‘cool’, if not cooler, in a t shirt and sneakers as you can in some forced, affected prep get up.

    You want to know how to look cool and fit in? Go live your effing life. Get some hobbies. Learn some new skills. Play sports. Have sex. Earn another degree. Read. Travel. Earn some money. Buy some property. Gain professional experience. Your style and clothes will follow and no one will smell the pretending on you like they most likely do now.

    And, while you’re at it, know when to stop fighting a fight you can’t win and don’t suggest strangers with heaps more experience and credibility on a given subject are bigots or snobs in a desperate attempt to save face. Oh, and stop name dropping Nantucket beaches.

    Time for a beer.

  90. @Al –

    Again, let’s not lose sight of what we’re talking about. Dressing ‘like an adult’ can mean many things, though I assume I know what you mean. It is not the same thing as “neo-prep” or an affected, assumed, contrived, head-to-toe prep persona-costume that this post is highlighting. I’m all for younger guys dressing more maturely and formally – that said, classic Brooks Brothers is a far cry from today’s Gant, Rugby, or York Street….and the many blogs they’ve spawned/thrive off of.

    I graduated undergrad in 2000. While I’m older than you, I’m not antique yet…..

  91. @AEV

    So if I went to prep school and I dress like it, I’m pretending? Still not following your there, man.

    As far as age goes, by the time I graduate college there’ll be almost 20 years since you graduated. Big difference stylistically speaking. Though a decade is not a huge amount of time, I think you finished school before the “prep train” arrived. Thankfully for me, it arrived right around my middle school days. So, instead of taking the neo-prep route, I opted for a more classic approach. Though don’t get me wrong, as much as I love J. Press, I don’t go to class dressed like one of their salesman…slim-fit (but not tight) ocbds and chinos generally. How was the prep look (as far as its popularity) on campus during your school days? Didn’t people wear jean-shorts and overalls back then? Then again, I remember my Dad rocking short pleated shorts sockless with tassel loafers back then then too. A lot of college kids in Boston these days are embracing the prep/neo-prep look. It’s refreshing to see Barbour, bean boots, and duffle coats instead of sweats (which are a minority here) on my way to class.

    And to give you a hint where I go to school…I’ll just say “take the T on the green line to Blandford Street”

  92. I actually liked Rugby. The way they presented the clothing in the ads was just god awful…But there is no law that you have to wear the clothes the way they’re presented…And they were at least slightly more moderatly priced than the Polo

  93. @Al –

    I lived in Boston from 1996-2002 (though I wasn’t a Terrier). My friends and I (and lots of strangers as it was Boston after all) were wearing Barbour jackets, Bean boots, OCBDs, chinos, penny/tassel loafers, New Balance 991s, Leatherman Ltd belts, Sperrys, Murray’s reds, J. Press, RL, Patagonia stand up shorts and snap t fleeces, Bean sweaters, some J. Crew, etc. (frankly, some of the same stuff younger guys are wearing now). The difference is that it wasn’t a “trend” and people weren’t ‘adopting it as a style’ – they either dressed like that because it was how they were used to dressing (most of the stuff was from their high school closets) or they didn’t.

    If you ‘went to prep school and dress like it’ now, you may or may not be pretending. For one, I never suggested that all people at prep schools do or should dress in the same manner. I know that’s not the case at all….many of my friends are proof. You yourself said that when you were in high school your natural style was t shirts and sneakers…..so, that was your style. Pretending may not be the perfect word…and I don’t know how many times or ways I can say it, but your style should naturally reflect and follow your life, your experiences, your hobbies, your surroundings, cultural tastes, social/family circle, etc. No one should wake up one day – as people do all the time – and decide, ” ‘prep’ seems cool now….I’m going to dress that way” (or, worse, believe that if they dress in what they believe to be ‘preppy’ clothes they will be signaling to others things like affluence or a specific background)….what you get when that happens is a hyperbolic, caricature of the style and everyone ends up looking like idiots and posers (and a lot of people end up embarassing themselves needlessly: http://www.mrporter.com/am/journal.mrp?feature=journal_issue141feature7&pageField=Page%203).

  94. AEV, I think what rings so patently false about your online persona (and it really is a persona) is that the person who can dress preppy, based on your standards, doesn’t exist. It’s certainly not you–you don’t even know the difference between come and, er, cum! (No, really, look it up–your decades of private education, beginning in the womb, must not have been at Peer Institutions.)

    We get it–you hate Castleberry (suspiciously much–do you have a thing for Asians?). But stop projecting your wild psychoanalyses of someone who really isn’t worth the time onto others. You choose to dress preppy. It isn’t an immutable characteristic inherited from the people you wish we believed you call mummy and daddy but are probably just Ma and Pa. Unless your childhood priest wore repp ties and OCBDs, I’m not sure what childhood experiences would have seared a need to dress in a very specific, deliberate way in your memory. (And if so: seek help.) You are discussing clothing on an internet site. By that act alone, you demonstrate a deliberateness that contradicts your thesis that you woke up one day as a small, small boy wearing a Shaggy Dog and never looked back.

    I have a photo of me wearing madras trousers, a blue blazer with gold buttons, a white shirt and a red tie with boat shoes at age 7 or so on my way to a yacht club dance. Do I win this contest? Do I get to wear madras now? Am I on the list? Have I been Honest? Do I get to go to Heaven? Oh, AEV, please do tell.

  95. New Rule: When AEV dressed a certain way, it was Natural. Just Boys being Boys. Now it’s a Trend, and people are Adopting It As a Style, and therefore it is Wrong, and Dishonest, and Bad.

    Actually, this is the same as the old rule: The criterium for dressing preppy is: (1) Be AEV.

  96. AEV, about those angels?

  97. @AEV

    Please be so kind as to advise which Beaufort you would choose to wear: “Classic” Beaufort or Beaufort? Thanks.



    In other words which is closer to the real McCoy?

  98. @AEV

    Though don’t you enjoy dressing this way? I do. It’s about enjoying the clothing you wear. You make it sound like you’re indifferent and you just happen to put on Brooks, Aldens, J. Crew, etc. just because it happens to be in your closet. You were drawn to these items because–you thought they looked good and were ‘cool’ to you (unless you’re a Patrick Bateman-type who only cares about labels and doesn’t even look at colors).

    I’ll be honest and say when I was on Nantucket, I wanted a pair of Murray’s reds. I figured, I was there, they looked great to me, and they were one of the softest pairs of pants I’ve ever tried on, so why not. It was a souvenir of sorts since I just visited the island for the day (I spent most of my time on the cape).

    And since you keep reiterating my earlier t-shirts and jeans comment, let me clear that up: I had no idea what style was. Therefore, these clothes weren’t so much my style, but things I just grabbed at the store to get out of their more quickly (it’s the opposite these days, I take my time).

    @madaket my high school’s priest wore khakis and boat shoes with a candy striped oxford cloth priest-collared button-down (I joke, yet I’m completely serious). Am I in the clear?

    @Christian I’m thinking of going to the Andover Shop tomorrow. Any tips on how to not have Charlie Davidson beat beat me up/throw me out the window of his store? I don’t have a very large budget since I’m a college student (I’m assuming he’ll talk if I buy something) and I want to pull some menswear knowledge out of the guy.

  99. I meant there…not their. Let me correct my own grammar before someone else does.

  100. Wow, FEC publicly admits to (maybe brags about) reading TEEN VOGUE?!

  101. @Al, Re: Charlie

    Say you’re a friend of mine and walk in whistling “So What” by Miles Davis.

  102. @AEV

    Your FEC fixation is taking a turn for the creepy.

  103. A.E.W. Mason | November 22, 2013 at 9:29 pm |

    Just a question. With reference to the fellow standing next to “Mr. Orange Vest”: Is that his shirt or his underwear showing between his trousers and his sweater? It looks like underwear but I find that hard to believe.

  104. A.E.W. Mason | November 22, 2013 at 9:30 pm |

    Never mind. Sorry, I see it’s the shirt. Whew….

  105. Am I the only one whom finds it odd the AEV was feature ON Fred’s blog???? Seems strange to associate oneself with something they so venomously oppose. No?

  106. @ cRc,

    Haven’t you noticed it? AEV and FEC are the same person. It’s just a Jekyll/Hyde creation to increase traffic to his blog and get some publicity.

    Only joking…

    … or maybe not? 😉

  107. There is something very unsettling about AEV’s obsession with MR.FEC. Jealousy does not look good on anyone. If he did despise this man and everything that he stands for it is odd that he visits the site and actually interacts with the community. I never visit places that I hate.

  108. Eljo
    AEV’s response is normal human behavior, almost everyone slows for a car wreck. 😉

  109. @ MAC

    Agreed most people slow down to look at a car wreck. AEV slowed down to take a look, then got out of his car, proceeded to explore the wreckage, took pictures and now is writing a conpresenvive play by play of the accident and is now working on filming a reenactment.

  110. @Lou –

    Honestly, I’d hunt for a vintage Barbour at this late stage (one that accomodates a snap in/sip liner would be best…not all of the older ones did). They aren’t making them like they used to. I prefer the Bedale as I find the Beaufort length odd and the rear game pocket is superfluous…

    @JazzMan –

    I think the spectacle that is Fred Egan is especially relevant given the topic of this and recent posts. And, I believe it’s a stretch for anyone who’s taken their affinity for “Ivy” clothes to the point of regularly reading multiple blogs on the subject to suggest someone else is ‘obsessed’ with just about anything related to the same genre….but, noted; thanks.

  111. @madaket –

    Huh? When did this become about you or how you dress? I certainly never took it there – my points were quite general, benign, and fairly straight forward and were all outlined in the context of this and recent posts about the rise of neo-prep. You took personal offense (bunot really, I suspect….this has oddly become about you attempting to dress me down for some reason…one more swing at the plate I suppose) and have bent over backwards suggesting I’m a snob, dishonest, a bigot, and inexcusably judgemental. You can keep beating that drum, and being a dick, but it won’t change my very simple and common sense perspective: dress naturally, based on your life and experience, not in a dress up, costume-y, trendy manner which tends to look forced, comical, and can run the risk of presenting an appearance which isn’t in agreement with any of your own natural experiences, skills, hobbies, background, affinities and/or accomplishments (e.g. not unlike how rediculous I would look dressed in head to to skateboarding gear, a full hip-hop inspired ensemble, surf wear, western wear or any number of other styles…). Legions of ‘style experts’ would and have said exactly what I just did…..but, you won’t have any of it. Right.

    Go ahead, misread that. Find a way to take offense. But first, stop name dropping Nantucket beaches and ironically giving into the temptation of telling us all more bits and pieces of your heritage and pedigree….

  112. As a twentysomething New Yorker who falls into the (neo)prepster category, I can assure all of you that I purchased and continue to purchase Rugby et al. because the clothes are fun as all hell to wear. I guess I just see it as youthful insouciance, and that’s always appealed to me. I mean… look how many people here are glad Rugby’s gone! I’d call that a success. In any case, anybody without a short torso that picks up 8″-rise pants when there are higher-rise options probably has bad taste. I’d say at least 25% of the stuff that’s been sold during the period mentioned by the author crosses the line from “go to hell” into “bad taste”.

  113. Dick declares it was just what everybody wore. True of many high schools and colleges, but probably not all.

    It’s worth remembering that, while the Ivy League college and their feeder schools had their fair share of smart guys (back in the Heyday), intelligence–and especially all-out brilliance–was downplayed. Who won the day? The self-confident, athletic, charming, easy-going lad who smiled easily (but not too often) and laughed heartily.

    This is not true of the Ivy’s today. Geeks, nerds, and wonks prevail. And there is no shame. Indeed, there’s a strange pride about it.

    What’s interesting isn’t that, once upon a time, the look was favored mostly because it was ubiquitous. What’s interesting is why, well into the 70s, 80s, and beyond, some continue to favor the look.

    I’ve gone on record as saying that it’s the most flattering of all styles for most men. High, wide shouldered jackets and pleats don’t help anybody.

    If some people see the look and hear “A Punk,” others hear 60s-era Motown. Some may hear Jerry and Phil.

    So long as no one hears Pat Benetar.

  114. Hey guys

    Some thoughts here from us in Prague, watching people who worshipped all-denim and ABBA haircuts just a few years ago to people who all want to act preppy. Number of Prep Schools here? Zero.


  115. @DCG-Welcome Aboard.

  116. @Lou

    The Beaufort is the real McCoy. I have the “Classic Beaufort,” however, which is coated with this new sylkoil that looks nicer, doesn’t rub off as easily, and smells slightly pleasanter. Purists or traditionalists, or whatever they’re called, would prefer the regular coating of the other Beauforts because they develop a beautiful patina with age. I also have a navy Bedale from the 90’s that was my dad’s. I like both, but would recommend the sykoil coating.

  117. I think people should wear the clothes they like. If the current swing of fashion helps keep some of my favorite brands thriving, so much the better. Please, hipsters, buy more Aldens!

    I think if you’re over 5′ 8″ or so, the Beaufort is a better choice than the Bedale. (Although my sister, at 5′ 8″, wears a Border and it looks great on her. Go figure.) And I think that if you want one with the old tartan and the snap-in liners, then you should buy a good one off eBay from the UK and have New England Reproofers re-wax and repair it for you… or call O’Connell’s, they may have brand-new old ones, they did last time I checked. I have an older one, but I have no opinion as to whether you should want an older one. Know-it-all message-board comments notwithstanding, the new ones seem pretty well-made to me. (For all of the talk of Barbour quality, there’s a reason that Barbour repair services 1) exist and 2) have months-long waits.)

    And to AEV, I think that if you went to school in Boston — not Cambridge, but Boston — then perhaps you don’t get to be the self-anointed arbiter of who gets to sport “Ivy Style”. Seriously, dude, you sound like a Brooklyn hipster with all this I-was-wearing-it-before-it-was-cool nonsense. Knock it off.

    (And before you start with me… I’m considerably older than you, and I was wearing it before the last time it was cool, and I grew up in an affluent coastal New England town and went to an actual Ivy school, so there.)

  118. Neo-prep is a new form of prep dress. It takes the old form and re-creates it for the time of today. Peopl would wear polos in light shades i.e. baby pink, blue, and green, cut off kahkis, flip-flops, and a cute tote.

  119. long live Rugby!

  120. Sheesh, guys. Relax. All this arguing about what constitutes genuine preppiness is very unbecoming.

  121. No idea where to put this, so I’m putting it on this post in case anyone catches it in the Latest Comments section. Rather fascinating remark in which the fashions of entire decades can be summed up by youth styles:

    “What did the 1990s “look like?” What did real people wear? Even now, nearly 15 years later, it’s kind of hard to say. There was the grunge trend, of course, and the mainstreaming of hip-hop gear.”

    From here:


  122. It seems I would be classified as a neo-prep, as evidenced by my blog: http://swisssartorialist.tumblr.com, and especially posts like these: http://swisssartorialist.tumblr.com/post/59035618633/loud-summer-chinos-in-summer-go-loud-or-go-home

    These aren’t Nantucket Reds, they aren’t even 100% cotton (2% spandex, sigh), but I love the way they look. I was born in Québec and raised (and still live) in Switzerland, and as such have no affiliations with preppy culture whatsoever. I’m not trying to make it look like I’m something I’m not by wearing those clothes, I simply think it looks really good, and therefore, I wear it. I see pictures like these:


    And simply like the look, and wear it because I like it. Therefore, I ask, what’s so wrong about that?

  123. I am not sure that Neo-Prep is not a useful term at all, but it is an interesting one. Has Prep really changed? Yes, there has been an immeasurable increase in the number of people writing about Prep, and Seeking To Be Prep in the last five to ten years. There is Prep and there is Not-Prep – hard to define – easy to recognize. Prep is a lifestyle, and a Prep’s Prep is a Practical Prep, as I write about on my modest site. Preps are not conscious of becoming Preps, They Just Become Preps. There is a core to prep, but it comes naturally, and should not be forced on anyone through the use of Advertising Campaigns, although it is obvious that some of these brands have hit the mark in showing us what could be the core of prep. What preps are raised to look for and practice (I like to call them the Tenets of Prep) are 1. quality 2. longevity and 3. utility 4. frugality.

    As I travel, as Preps have done to Europe and elsewhere through the ages, I have developed a sense of what it is like to not have a huge wardrobe or house in which to store my belongings, and belongings, and fashion, are how many people define Preps, although Preps should not be defined only through these things. I guess you could call it Hobo Prep: “Hobo Prep is a Practical Prep. Its the Prep’s Prep Style. For a Hobo Prep is a Prep’s Prep, and is in a sense the Ultimate Prep. Put your beanie in the back pocket of your newly tailored Brioni suit pants if its practical – easy to access and easy to walk with, and a much needed protection if you do slip on the ice on the cobblestones. ” Ultimately however, “Hobo Prep” is nothing more than “Prep”, and perhaps like Neo-Prep, doesn’t deserve a category of its own. Hence the lack of hyphen, For A Hyphenated Prep Is No Prep, as we Preps do not believe in a hyphenated world.

    I say this while writing this from a cafe, where I can feel the presence my warm woolen gloves in my other back pocket as I sit. Ultimately, Prep is about a way of life, and a way of raising children, or being raised as one yourself and following the Tenets of Prep – these are more important than any one fashion item to any Prep.

    The Hobo Prep 2013

  124. “Neo-prep” is when people dress in traditional style clothing while they are, in fact, altering the style to insinuate the “nuances, realities and experiences of their own, actual lives.” The world changes. The environment changes, the workplace changes, infrastructure changes, language changes. To expect that a certain clothing style (which is itself an amalgamation of items borrowed from other times, places and classes) will remain constant, or that they shall be limited in perpetuity to a particular geographical area or to folks with a specific financial or social profile is folly. Nowadays, even people other than cowboys wear cowboy boots.

  125. “Nowadays, even people other than cowboys wear cowboy boots.”

    True, but they do not call themselves cowboys (but remember the Urban Cowboy phenomenon?), and more importantly they do not think like cowboys. This is the difference between prep and Neo-prep. Being preppy is a way of living, including a way of thinking and a way of acting. It is not just a way of dressing. Neo-prep clothes are rarely preppy clothes, and Neo-preps rarely act preppy.

  126. Would love to read a follow up to this, I’d still like to see neo prep continue to thrive, but it seems to be difficult….

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