Ivy Trendwatch: All Roads Lead To Ivy

and those that don’t, lead to prep.

So relax: There’s hope for the future. It’s just that the future includes critter pants.

This chart from that other world known as 2012 brought out some lively discussion. Fashion cycles churn fast these days, so you never know….

67 Comments on "Ivy Trendwatch: All Roads Lead To Ivy"

  1. Christian, your website inspired me to blog. Thanks for your guidance when I had questions. It was very kind of you to take time to answer questions. I have almost 2000 hits!

  2. But what road leads to WASP 101?

  3. Poor Richard | May 18, 2012 at 1:31 pm |

    “Do you have a pretend friend with a private jet who flies you to the Rugby Cafe for lunch?”–>Yes, and I swear my Dad went to Yale–>WASP 101

  4. Johnny Reb | May 18, 2012 at 1:38 pm |

    I think its hilarious that some people can’t tell Richard Wasp is a fraud! How pathetic!

  5. “Are you a dweeb?” –> Yes
    “Did you have no friends in high school?” –> Yes
    “Are you pretentious?” –> Yes
    “Do you like to play ‘dress-up’?” –>Yes
    “Are you a tool?” –> Yes
    “Do you like to play ‘pretend’?” –>Yes
    “Are you lacking in taste and sense?” –> Yes
    –> WASP 101

  6. FIE! I protesteth not and still they seek my ruin!
    Arrows. Arrows of mockery and hate fly!
    Targeting the damnation of my soul and piercing
    with vengeance !!

    Daggers of venom at the ready upon the least
    hint or idea of my work…stabbing me ever inward!!

    Quote my Raven , “NEVERMORE, and NEVERWAS!”

    But curse me with unbridled ridicule……
    seeking my doom, sealing my fate….

    NO. Have I not experienced personal air travel
    and a weekend romp in a friend’s Morgan?

    NO, I have not!! Mine own tongue condemneth me!!
    ASCOTS and VELVET SLIPPERS,where are thy reward??
    Knighthood of WASPDOM. INSTEAD……peasantry.

    Wasp101 is my sentence with no parole.

  7. Johnny Reb | May 18, 2012 at 3:28 pm |

    Can anyone take a guess at what Richard Wasp does for a living? Where do all the Rolls Royces and vintage smoking jackets come from? Could he have inherited them from his great-grandfather, the Duke of Douchebagery?

  8. He states he is in the PR business with many
    politicians as clients.
    There may be the answer to it all as well.
    Applying the bs techniques of the PR business to
    this personal quest of needing, dying to be WASP
    by way of a blog.

    Twas failed from the start.

  9. I believe people failed to note the title: “What Men’s Style Blog SHOULD You Be Reading” (Emphasis added.) No one should be reading Wasp 101.

  10. Honest Abe | May 18, 2012 at 9:23 pm |

    And yet, every morning we check out his blog, don’t we?


  11. Ralf Loren | May 18, 2012 at 9:31 pm |

    At least Richard steers clear of Tuckernuck atrocities and tries to focus on the Real Thing.

  12. Johnny Reb | May 18, 2012 at 11:22 pm |

    The Real Thing? He says he goes fox hunting on a English estate and jets down to D.C. for a cup of coffee, yet the interior of his hiouse gives away heverything! I’ve never seen anything so unjustly pretentious

  13. finally checked out the WASP101 site. I didn’t think it was bad, lots of nice pics, mostly Polo stuff. Lots of old Polo ad prints, a lot stuff I admit owning. A whole lot of costume pics of the blogger, mostly pretty good looks. I enjoyed the photos of the cars, but no motorcycles. I did like the photo at the bottom left margin of the English Springer spaniel holding the pheasant, I got a similar one on my dresser, but it is my dog.

    What didn’t I like?

    Belgium loafers

    99.9% of the preppy women, except in Ralph print ads, weren’t dressed preppy.

    Something Bush One did, wearing a collar pin with a button down collar shirt.

    I like Ivy Style better, it’s more academic.

  14. This list is all wrong, Laguna Beach Fogey doesn’t seem to have made the cut.

  15. Sixties Ivy | May 19, 2012 at 4:57 am |

    Richard is not The Real Thing, but the men’s clothing he portrays is The Real Thing, i.e., Authentic Ivy. Even Ivy Style, which is the indisputably best Ivy blog, sometimes strays from authenticity when it portrays modern polychromatic variations on the Ivy theme.

    By the way, let’s not forget that for many (most?) old time Ivy adherents, “Ivy League” had nothing whatsoever to do with the football connection. The Ivy League connection was with the ivy-covered mock-British buildings of Ivy League universities.

  16. Theoretically, All clothing not bought at Brooks bros., J. Press, et. al is not Ivy, but pretenders, illegitimate. All those “ivy” shops that spread across the USA, in every major city and mostly college towns, in the late 40s and early 50s are illegitimate. Ralph Lauren and the rest are illegitimate “ivy”.

  17. MAC:

    That’s why engaging in Richard/WASP 101 Bashing is meaningless. If he’s a pretender, so are the vast majority of us. How many of us are blueblooded New Englanders born and bred?

  18. Christian | May 19, 2012 at 12:08 pm |

    There are only two alternatives, “pretenders” and bluebloods?

  19. Diogenes, exactly!

  20. How many of us are blueblooded New Englanders born and bred?
    NO. It’s how many of us start a blog called WASP101
    and not let our REAL life speak for itself.

    How many use a blog as a ring announcer to proclaim to all,
    Oh pretty please? Let’s see, I like – Tartan? Check.
    I like – Madras? Check…..Hmmmmm can a WASP wear
    Jeans? I better review that one half a dozen times a
    year and try to disguise it as a new subject I’ve never
    addressed before.

    Is it ok if i rub my MASSIVE INSECURITY in your
    face in my pursuit of your acceptance and at the same
    time arrogantly refute the kind advice GENUINE WASPS
    offered me at the beginning of my blog?
    As well as claim I am a legitimate authority on
    WASP style.

    Gentleman, you’ve either got or you haven’t got
    style. You don’t need the world to parade yourself and
    make sure EVERYONE understands you’re a WASP.
    Richard stood a greater chance to be invited to
    a “WASP” country club as a guest, obviously a
    goal in his quest, by just being himself and seeing
    where life leads, as opposed to “marketing” his
    REAL LIFE on camera and living out a script
    telling you how you are to see him. The exact
    opposite of of how to get the results he is looking for.

  21. Jinx
    I agree, but tend to be less critical than you. Yes WASP101 is a little put offish since I’m ICWT.

  22. Archimedes Hartwell | May 19, 2012 at 2:36 pm |


    Let’s all slow down a tad. It’s only clothing, after all. Nobody needs a special pass to purchase a Brooks blazer and oxford cloth shirt. Richard may be projecting a bit but it’s not as if he were proclaiming some kind of heresy. A poseur? Not necessarily. He really wears that stuff.

  23. “Nobody needs a special pass to purchase a Brooks
    blazer and oxford cloth shirt”……..

    Archimedes? It is RICHARD you need to tell that to.
    He is the one obsessed with finding a special pass
    called , WASP! in order to justify himself.
    He can wear whatever wants. It is the fact that
    insecurity ,lack of confidence is the wardrobe of his spirit.

  24. Aeschylus | May 19, 2012 at 7:05 pm |

    The Goony Bitch posts an article on how to masquerade as a European and fails to realize how hypocritical she is when she verbally bullies Richard de Wasp Cent et Un.

  25. LB Fogey

    Finally got around to your blog, I liked it, and you are right we Americans are parochial, we don’t apologize.

    We seem to share a shoe fetish, most of mine are tan, followed by cordovan, white buck, only own one pair black. Your Anglo-Continental taste show in your square toed shoes, I appreciate them, but not my cup of tea.

    I don’t speak French, so I have no idea what those post were.

    Watches, I prefer cheap thin tanks. Advise from 20 years your senior, Rolex s are great sports watches, but they will prematurely wear out your favorite shirt and jacket cuffs.

    The motorcycle representations, Italian! Considering all the great British marques I was disappointed.

    On a serious note, Bean, Tolkien, Waugh and more, thumbs up. I was touched by the last paragraph of your memorium to your father.

    Thanks, I’ll return.

  26. @Sixties Ivy

    “The Ivy League connection was with the ivy-covered mock-British buildings of Ivy League universities.”

    Mock-British? Many of those Ivy League schools actually pre-date the USA, so in fact they WERE British at the time. If you want to get technical about it.

  27. Sixties Ivy | May 20, 2012 at 4:46 am |

    @ Ivy Drip

    I stand corrected. Sorry for the anachronistic error.

  28. Christian | May 20, 2012 at 6:37 am |

    I share a lot of similar tastes with LBF too.

    I mean, except for the Nazi sympathies and stuff like that.

  29. Christian
    I don’t think LBF has Nazi sympathies, Catholic, nationalist, anti-immigration and anti-Islamic expansion yes, Nazi no.

  30. Johnny Reb | May 20, 2012 at 11:39 am |

    Richard Wasp’s clothes do not bother me as much as his pretending to be a true blueblood. He could blog about style all he wants without mentioning how he goes fox hunting on English estates or how his aunt picks him up on Thanksgiving in her 80 year old Rolls Royce. Everyone sees right through him and that is the pathetic part, not his taste in dress.

  31. Ox E. Moron | May 20, 2012 at 8:48 pm |

    Johnny Reb and others:

    You fail to appreciate the fact that Richard is a master of humor. His aim is to parody pretentious wannabes.

  32. Johnny Reb | May 20, 2012 at 9:24 pm |


    I don’t think that’s accurate at all. His grammar is horrendous. His writing is laughably ineloquent. His followers are dull-minded. His comment section is censored. He assumes different names to compliment his pieces (it’s painfully obvious). You should take another look at his blog.

  33. Ox E. Moron | May 20, 2012 at 10:22 pm |

    @Johnny Reb

    I was being ironic.
    That’s why I chose a nom de plume including “Ox” and “Moron”.

  34. Richard Cent et Un | May 20, 2012 at 10:35 pm |

    Whats wrong with my spelling, word choise, and grammer? You oughta check you’re grammar.

    Also, it’s complement, not compliment!

  35. whoa….save some of the fraud bashing for Castleberry.

  36. Richer Richard | May 21, 2012 at 5:56 am |

    Does anyone else wonder why Richard’s wife stopped taking pictures of him? He used to post picture after picture of him in his silly outfits. Now it’s just Ralph Lauren ads.

  37. Philly Trad | May 21, 2012 at 7:01 am |


    Who is Castleberry?

  38. RR
    Unless a blogger worked in a clothing related business, sooner or later one would run out of things to photograph. That’s most likely the reason so much of the content on most blogs are not original. That’s why I call Ivy Style academic, almost all the post are interesting and one learns somethings.

    Ralph Lauren ads aren’t a bad thing, especially as they relate to the Ivy look since around 1970. Prior to the net, print ads in magazines, and his full blown “life style” products, RL produced brochures distributed to the ivy shops around the country. From a historical prospective, it would be interesting to post them in chronological order to visualize how his clothing changed from a small clothing company to a “life style” conglomerate.

  39. For Richard, For Poorer | May 21, 2012 at 8:23 am |

    Who knows? Maybe she got tired of snapping glamour shots of Pretty Ricky, packed up the Dachshund, hopped in the Rolls Royce, and scooted on out of West Virginia.

  40. Johnny Reb | May 21, 2012 at 2:30 pm |

    Richard Cent et Un:

    You aren’t Richard WASP, are you? Please excuse my drunken grammar, I was typing on my iPhone at a party. Besides, I’m a commenter, not the blogger. “Choise”? “Grammer”? Please tell me your another impersonator trying to be funny.

    Moron: I was wondering about your name. Sorry for not catching the humor!

    Green: We should talk about that. If you question his prep authenticity, he’ll delete your comments. Anyway, I think the style is something that should have been shed sometime around his college years.

  41. @ Johnny Reb – Yes, Fred deletes any dissenting opinion….there’s no intelligent dialogue on that site at all. My fundamental issue with him is that he knows absolutely nothing about the prep aesthetic. And how could he? He grew up in some small Texas town. Everything he’s learned is torn from the Rugby catalog….which itself is a caricature of prep style. He has crap taste and a penchant for large logos and ersatz crests. Tacky to his core. And absolutely no sense of humor about himself.

  42. Green
    All of you say may be true, but exactly why would someone that grew up in a small town outside Dallas-Ft worth not know something about the “prep aesthetic”?

  43. @ MAC
    Just my personal opinion but I believe that unless you grow up in the prep community you really can’t know what it’s about. You can observe and learn and mimic but you can’t know the why behind the what….if that makes sense.

  44. Green
    I think many think shops weren’t selling ivy style clothing outside the NE. Don’t forget this was the vogue of dress trough out the USA in the 50s. Most all major cities and university towns had ivy shops, many that have been around since the late 40s, some still exist.

  45. Johnny Reb | May 21, 2012 at 5:17 pm |

    MAC: Castleberry’s blog isn’t Trad, it’s prep. Hence the name, Unabashedly Prep. I think Trad is accessible to anyone, but the go-to-hell prep look is somewhat exclusive to the New England WASP establishment.

  46. Reb
    I never heard of the term “prep” or “preppy” in relation to clothing till the 1980s. The first I ever heard the term “preppy” was in the movie Love Story. I grew up in the 50s and 60s, in the South and Mid West, we always called it ivy league. We bought what you call “prep” and “trad” in the same shop. I guess what you call “trad” is what I call are dress or work clothing. What you call “preppy is how I dress casually. I costume myself appropriately for the occasion.

  47. Johnny Reb | May 21, 2012 at 6:46 pm |

    MAC: I wouldn’t know much about the 50’s or the 80’s because I’m only sixteen, but I think Ivy Style has, in a number of posts, established the difference between preppy and Trad. Heres one:


  48. Reb
    I’ve read that post, but thanks. I understand the difference as defined here, but I think of it like a Ralph Lauren Shop or Brooks or J. Press, in all of them you can do both. I’m 60, the funny thing is that in college everyone wore bell bottoms, chambray work shirts and Frye boots, I was told I dressed like an old man. A decade later in the 80s, I was cool again, they called me preppy. For the last decade, everyone dresses in black Italian looking suits and but ugly shoes and they tell me I dress like an old man. I think I’m due for at least one cool decade before I die. 🙂

  49. Castleberry’s most grievous flaw is, as you said, his total lack of self-awareness and sense of humor. I understand if he doesn’t want his comment section to become a discussion forum (CC is incredibly kind for letting us prattle on over the same subjects endlessly). I’ve kept an eye on his blog for about a year now, and he’s actually pretty good at not explicitly saying what’s prep and what’s not. Except that, of course, he named the blog “Unabashedly Prep,” so there are are some implicit prep proclamations going on. And because of that title, he has become a posterboy for this neo-prep movement.

    Wearing double monkstrap shoes (why did those become popular?) with one strap undone, a twisted tie knot with a pinned buttondown collar, and self-applied painted khakis, all at the same time, *does* look clownish to me. That’s his style, I don’t have to like it, and I don’t think “prep” is so sacred that it needs to be defended from his interpretation of it. But he does it as if there is nothing ridiculous whatsoever about stuffing a pocket square in his denim jacket pocket. You can admit that you look silly while still owning that look.

    Also, I think Rugby was started to just contain all of Polo’s increasingly absurd items into one absurd label. Polo is far more restrained now than it was in the years before Rugby came about.

  50. Dan
    I believe Rugby is probably the new Chaps, lower price point and over done for the younger crowd.
    Double strap monks? blame that on Ralph L., maybe he should spend more time in NYC than the ranch. Yes, it’s a dog, they should have modeled it like the 60s Cole Haan, it would have sold like hot cakes, we would have been grateful.

    I cut Castleberry some slack, first off he works for RL, is a fashion photog in NYC, and admits to having some paid content on his site. In the context of where and what he does, he really isn’t that far out of bounds, it’s par.

    Painted khakis, I wear a pair, to the paint store for more paint. L.L. Bean hunting boot, I own two pair, I upland game hunt in them. The great thing about others wearing skinny jeans and high water pants, is that it guarantees me looking better.

  51. Double monkstrap shoes are fine. Leaving one of the buckles undone, however, is ridiculous. It’s the same level of clothing hipsterism as leaving a sleeve button undone. It’s ostentatious and therefore gauche.

    IMHO, of course.

    And yes, CC, is a great blog host. He has a knack for knowing where to draw the line on discussions, and I thank him for his numerous indulgences towards all of us who have received them.

  52. Arthur Orton | May 22, 2012 at 11:22 am |

    Ah, now I understand: this thread is why Richard belatedly posted this ancient photo (CC has tossed the old newsboy cap, I hear):


  53. Henry
    IMHO, I think you will see a lot owners of that particular Ralph double buckle monk worn without the top buckled, it’s uncomfortable. The vamp is too high, it’s like they intended to do jodhpur boots and ran out of leather. 🙂

  54. MAC,

    People shouldn’t buy, or wear, shoes that don’t fit.

    Not that I expect that to happen any time soon. 🙂

  55. Johnny Reb | May 22, 2012 at 1:40 pm |

    My point was not to specifically criticize Castleberry’s style as much as his posing to be a prep. Emblazoning a crest on a blazer when you did not go to a boarding school is absolutely ridiculous. Buying a 30 year old car to give off the impression that daddy passed it down to you is absolutely ridiculous. Dressing like a twelve-year-old school boy when you’re in your thirties is absolutely ridiculous.

    I’m emphasizing that Trad is a style that anyone can respectfully wear, no matter their who they are. Prep, on the other hand, requires the background and lifestyle.

  56. Ralflorins | May 22, 2012 at 9:41 pm |

    Sorry Johnny,

    The whole ivy/trad thing is about posing…and we love doing it.

  57. Orgastic future | May 23, 2012 at 12:45 am |

    Wow you guys are all pretentious jerks with the class of a summer school in Chernobyl. I love unabashedly prep and other blogs that celebrate awesome lifestyles. Who would’ve thunk that after all of these years Holden Caufield would still be right about the classlesness of the culture.

  58. “Orgastic future” and “classlessness of culture”… Gatsby and Rye, well done.

    I don’t get the Chernobyl reference, no one lives there.

  59. Hey, love it all you want. To each their own. Enjoy Fred’s awesome lifestyle. BTW, I made air quotes when I typed awesome.

  60. The dude at WASP101 is a pasty chubby blowhard pretending to live in some country estate. Just looking the pics of his bland style provides a lot of tells. The cramped background of his living room suggests the dimensions of an 800 sq foot efficiency apartment. Pathetic doesnt even begin to cut it. Its embarrassing to observe due to his lack of self-awareness.. I can say that it is satisfying to join others in mocking, especially when he tries to mock the regulars of IvyStyle.

  61. Castleberry is a pretender. Should I spot his fat Rachel Maddow look-a-like profile in Melon’s he’ll be wearing my bloody mary on his painted khakis (inspiration, Fred?). Dressing like Emmet Kelly or playing dress-up is a sign of a pathology – or several. Too short blazers with gorges on the shoulders, little sister’s pants on “men,” and deep v-neck tees and monk straps without socks are not preppy, ivy or trad. What can be said is most of the preppy, ivy and trad style blogs constitute an echo chamber of the ersatz.

  62. Hardbopper | August 5, 2020 at 2:57 pm |

    I was on track until I hit the RL roadblock. Ivy should be to the right of prep; Polo to the right of Rugby.
    I’ve always found RL to be a little bit overstated.
    Does this make me “Trad”? I guess you can put me in the “fogey” camp, although I prefer “classicist”, or maybe “doctrinally orthodox”.

  63. Henry Contestwinner | August 5, 2020 at 6:50 pm |

    2012 was another world indeed….

  64. Haha indeed– the readership of this is full of wannabe preppies without ivy league degrees who obsess about authenticity!

  65. Old School Tie | August 6, 2020 at 10:22 am |

    He DOES look like a Iesbian dressing preppily….I could not put my finger on it until I read this thread.

  66. This blog is one of the few left with any regular activity and/or new posts from time to time. So many of them ceased posting within a few years of that 2012 high water mark in the #menswear movement. Or, they commercialized and are now either a shell of their former selves or nothing at all like the original. It makes me all the more appreciative that we still have Ivy-Style; let’s hope it’s still around for at least another eight years.

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