Is Ivy Cool?


Answer: only as cool as the guy wearing it. Cigarettes and sunglasses help. Here’s a sampling of images we’ve run over the past five years. — CC











64 Comments on "Is Ivy Cool?"

  1. Hey–I posted less than an hour ago about the first (Norman Hilton) ad.

    There he is. Cool.

  2. Christian, may I make a suggestion?–an addition to the photo series you posted.

    An album cover. Among, I’ll venture, the coolest. Ever.

    The Ornette Coleman Quartet. “This is Our Music.”

  3. Clothes aren’t cool. People are cool.

  4. Comparing the first two images, the first one is not cool. It is a put on, an act, an attempt to play a role within ones comfort zone. The second one is cool. The good but not expensive haircut for example, demonstrates self reliance, experience, and confidence while exploring outside ones familiar surroundings.

  5. Norman Hilton man looks cool but leaning against a petrol pump with a ciggy in your mouth ain’t smart!!

  6. Clothing is never going to be able to make an uncool person cool. And it would take really bad clothing to make a cool person uncool.

    It bears mentioning that cool is a questionable goal. Mr. Short Pants and Sunglasses Indoors is probably the coolest of this bunch, but also probably a dick.

  7. Agreed Madaket.

  8. SE, totally agree about the Coleman cover.

  9. Is AEV cool?

  10. Lisa –

    He sure looks pretty cool to me. You?

  11. @Lisa,

    I’ve known AEV for a decade. Yes, the dude is cool. Opinionated, stubborn – argumentative even – but, one of the coolest, well-rounded, loyal, funny, intelligent, and diverse (and typically “right”) dudes I know.

  12. Based on observations of the comments left by followers of this blog and others like it, I’d say no, Ivy isn’t cool. You can’t be a curmudgeonly stickler for rules and expect to be cool. Rules are anathema to cool.

    That said, ‘cool’ has plenty rules of it’s own, but disavows all of its own rules. Cool isn’t even cool, really. So who cares? Fuck cool.

  13. I thought the 2nd image was cool when I posted it on Tumblr last August.

    But seriously, I agree wholeheartedly with OCBD.

  14. Christian, good job pulling it together, blue shirt picks up the jacket nicely. All you need is to be taking a strong drag off of a filterless Lucky Strike. You know, the manly kind of drag where your cheeks suck in. Cool man, cool.

  15. Clothes are definitely cool. If they weren’t nobody would be wasting their time blogging, commenting here, etc.

    I think the Ivy league look is cool if it’s well exectured. Everything goes well together with many options. It’s nice to be insprired by such rich pallette. Poorly executed with cheap clothes and it just makes you look like your wearing a costume. It’s definetly something that you can draw modern inspiration from.

  16. But then, there’s that above-it-all quality that’s even cooler than cool. By this standard, Archibald Cox was cool.

  17. Is Christian cooler than AEV?

  18. I saw AEV on Unabashedly Prep in brown shoes, a pink spread collar shirt and a madras tie in the city. Not exactly formal business attire and definitely not cool.

  19. @Nathan

    Judging from our photos, that’s like asking what’s cooler, heartburn or gas.

    But like I said, sunglasses help.

  20. Coat and tie is cool.

  21. @Eljo –

    Huh? I saw that same pic on UP and thought it was killer (a rarity for that site). A (well fitting, custom) navy suit, solid light pink spread collar shirt, brown cap toes (what he was wearing in the pic you’re mentioning), and a sterling engine turned belt buckle/belt, is certainly business attire. The, “in the city” matra is tired – we’re not living in 1955 – and, DC isn’t NY – and, the pics were taken in upper NW DC (Cleveland Park, as the comments pointed out) which is more suburban CT than it is 5th Avenue.

    The pic, I believe, was also taken in the middle of a DC summer – so, I see nothing wrong with a cotton/madras tie. For all we know, he wasn’t conducting formal business of any kind that day…..prob wasn’t if he was being photographed by Fred.

  22. @james

    Forgive me, I did not know that it was for a photo shoot and not a formal business day. That makes more sense, but you say well fitting and I say too small. However, I am not a young buck, but I am not a septuagenarian either. We also must do business in very different places.

  23. The place to go for cool looking men in tweed smoking filterless lucky strikes clearly is Mad Men 😉

  24. Wow, Thomas and James write almost exactly like AEV… hmm.

  25. Yup, I’m convinced. AEV is writing as Thomas as well as James. Note their tones, style and most notably the use of the “dash” ( – )

    How cheap.

    Here is a sample of Thomas, James and AEV’s writing…

    Comment by Thomas — November 14, 2013 @ 12:31 pm

    I’ve known AEV for a decade. Yes, the dude is cool. Opinionated, stubborn – argumentative even – but, one of the coolest, well-rounded, loyal, funny, intelligent, and diverse (and typically “right”) dudes I know.

    Comment by James — November 14, 2013 @ 7:45 pm
    @Eljo –

    Huh? I saw that same pic on UP and thought it was killer (a rarity for that site). A (well fitting, custom) navy suit, solid light pink spread collar shirt, brown cap toes (what he was wearing in the pic you’re mentioning), and a sterling engine turned belt buckle/belt, is certainly business attire. The, “in the city” matra is tired – we’re not living in 1955 – and, DC isn’t NY – and, the pics were taken in upper NW DC (Cleveland Park, as the comments pointed out) which is more suburban CT than it is 5th Avenue.

    The pic, I believe, was also taken in the middle of a DC summer – so, I see nothing wrong with a cotton/madras tie. For all we know, he wasn’t conducting formal business of any kind that day…..prob wasn’t if he was being photographed by Fred.

    Comment by AEV — November 11, 2013 @ 10:23 am
    I stand corrected – there is a single, ‘washable tropical’ (how’s the ‘washable’ suit stood the test of time….?) suit pictured in the Brooks catalog with a OCBD. Every single other pic of OCBDs – dozens of them – has them paired with casual, non formal suiting (and, the one other (formal, wool) suit is pictured with a point collar shirt).

    Yes, I do indeed link my preferences to tradition and custom – both my own personal traditions and those that happen to be (ironically) profiled in the Brooks catalog from 1980…..perhaps those that believe OCBDs are well-paired (and well established) with formal suiting should spend some time studying it.

    Comment by AEV — November 12, 2013 @ 9:13 am
    @Malvernlink –

    I think – for the non-rubes – it’s fairly obvious that I’m only using the term “formal business suit” to differentiate and avoid confusion. It’s a general phrase, used only in this instance to clarify that I’m not referring to cotton suits, seersucker suits, corduroy suits, linen suits, washable/dacron suits, leisure suits, skinny/trendy/shrunken suits, etc. – all of which would be far more acceptable with more casual shirting and none of which would be acceptable in a large percentage of today’s white collar, business settings.

    I understand that people – like you, I’m guessing – who like to wear OCBDs with suits and ties will disagree with me. That’s ok with me. But, to suggest, with an aire of certainty and defiance (self ascribed ‘sophistication’, even!), that no debate exists about the appropriateness of OCBDs in formal/business settings (mostly because of personal taste, anecdotal historical cherry picking, and/or an odd fetishization of trad style), is pure foolishness.

  26. I’ll await AEV’s response during “working” hours.

  27. Are cigarettes and jazz cool?

  28. Cool is about being, not looking.

  29. Ivy gents stopped using the adjective “cool” when they graduated from high school. Ivy style is about being an adult.

  30. Apparently smiling isn’t very cool.

  31. @emjkmj –

    Ha ha – I love the ‘use of the dash’ conspiracy theory. I have, from day one – and unlike many other commenters – always provided my actual initials (and email address to CC). I also know it would be very easy for CC to cross reference IPs addresses and know if people were commenting from the same computers under false/different names….i’m no IT wizard, but isolating my IP address is how Fred Castleberry has been able to block me from commenting over at his little masquerade ball….

    And, as years of comments on here and other blogs have proven, there’s no need for me to manufacture support from strangers, friends, or colleagues…..

    But….now that you mention it….amazingly your blog comment syntax, use of fragments, punctuation, and style is also very similar to numerous other commenters – maybe, just maybe, you, me, and CC are the only ones commenting on here!

  32. Funny if Curmudgeon turned out to be a college sophomore.

  33. @AEV

    In my briefcase I have two iPhones (one work, one personal), a cellular iPad, and a Laptop… all of which has different IP’s, let alone my office computer and my home computer. So that isn’t a very good defense counselor.

    Secondly, for the guys who itches at a chance for any fight, I find it odd that you never come to your own defense of your photos. When the original photos of yourself posted on UP, a fresh new commenter who came to your defense and argued on your behalf against everyone, all while you didn’t say a peep. Like Thomas and James, that commenter also argued with everyone in your exact same tone and syntax. As much of a jerk I think you’re, you do have a very strong command of the english language, and have a very unique polished writing style. You should love the “dash” conspiracy, it was your tell-tale sign. Take a look through hundreds of pervious comments, I think you may be the only person on this site who uses them in the manner that you do (besides Thomas and James of course).

    I didn’t expect you to come clean on this, just having a little poke, at the guy who loves to poke.

  34. @emjkmj –

    I come to my own defense, using my own initials, all the time and believe I’ve made it clear I have nothing to hide and no reason to create ‘fake friends’ or supporters. You may think I’m a jerk, but the reality is that the opinions I hold are shared by lots of other people….just how it is. As any fair analysis shows, it’s hardly just Thomas and James who’ve agreed with me across the many months/years I’ve been commenting on this blog…if it’s easier/more comfortable for you to chalk them all up as phony duplicates, so be it.

    I have one laptop and one phone, both of which operate off of the same IP address. Again, I’m no tech expert….if I was I suppose I could have bothered to find a way around Fred blocking me over at his nut house. Sounds like you are, in fact, well-versed in skirting IP blocking and the ways in which commenters might of obfuscate their identities…….figures, doesn’t it?

  35. I just checked and James, Thomas and AEV all share the same first two digits of their IP addresses, though I don’t know enough about IPs to know what that means. It could simply mean they’re all in Washington DC, and possibly the other guys are friends. In which case, cheers to AEV for having bros willing to back him up.

  36. @AEV,

    AEV, so two people who i’ve never seen comment, come to “your defense”, and only yours… writing exactly like you on… in your same local? Yea right. They also just both happen to pop on the blog yesterday.

    You do defend your opinions and comments and love to argue with anyone one any subject, but never the photos of yourself.

  37. @Emjkmj (btw, very interesting what one finds when those letters/initials are Googled…)-

    You really are reaching here, huh? Is surprises you that my friends live in the same city as me? While I have (multiple) friends/colleagues/co-workers who are named Thomas and James, I have no idea exactly who these guys are. If they’re the Tom and James I think they are, then yes – they live near me and, as far as I recall, are relatively new readers of this blog. This most recent post, for whatever reason, led to personal critiques and criticisms of me…this hasn’t happened in some time; hence their comments. That said, for all I know ‘Thomas’ and ‘James’ aren’t real names at all – they could indeed be you given your expertise on such concealment…I’ve always sensed that you harbor a love/hate dynamic for me.

    “The photos of myself”, which are 2 1/2 years old at this stage, consist of 5 photos and 5 photos only. I refrained, deliberately, from commenting directly on them as they were posted on Fred’s site as I felt it would have been forced and inappropriate for me to do so (I did leave a single, general comment at the end of the week/spread acknowledging the many comments and confirming they were of me). That said, in the ‘GQ treason’ post on this very blog (from just two days ago) I do indeed defend the pictures using my initials….as I have a number of times in the past. So, your assertion that I’ve ‘never’ defended or commented on the old UPrep photos is just plain wrong (and strange given how obvious your incorrectness is)….sort of like your odd disbelief that my friends live near me.

  38. @AEV

    “maybe, just maybe, you, me, and CC are the only ones commenting on here!”

    Now that would be cool!

  39. @SE

    Cheap is just that. Cool assumes perception. So he (Cox) may be in some eyes. Just as each like minded group has their definition of cool. Obviously my definition would differ from a community of tech geek’s. Likewise Hipster believe that tight fitting clothes are cool. Those with common sense know better…

  40. @AEV,

    You’ve sensed a “love/hate dynamic” from me (When you’re a jerk, i’ve called you out, when I think you’re funny or right, i’ve agreed) You’re a megalomaniac… which explains why you could never allow others to criticize you and sit on your hands. Also, I am a long way from D.C… they aren’t my IP address.

  41. Emjkmj-

    No delusional fantasies of power or omnipotence here. You accused me/my friends of something incorrectly. I defended myself. You brought that to me – not the other way around.

    It’s an odd person who (grasping at straws) lobs (factually broken) criticism at a stranger and then, when that person defends himself, accuses them of being delusional and maniacal. If I’m a megalomaniac, you’re a glutton for punishment.

  42. Here are two gentlemen wearing sunglasses: Are they cool? (AEV undoubtedly thinks so.)

  43. The photo series hints at CC’s (possible) take on “cool.” No surprises. Plenty of cigarettes, sunglasses, and ennui-inspired frown. The usual kit. The three, put together, may very equal “cool” in any setting. Add a beer or drink in the hand or a trumpet about to be played, and the coolometer might just break.

    I can’t say I’ve ever aspired to “cool,” but I know the popular take on “cool” when I see it. Is “Ivy” cool? Well, Ivy’s ascent coincided with the advent of rock n’ roll and James Dean and McQueen and so on. So, the affiliations have staying power. But before Ivy, there was veddy British Brooks. And I’m not sure how many of us affiliate WASPy-Fogey-Anglophilia with cool. Evelyn Waugh was cool, though. Right?

    AsI think about it, some of the most composed, self-confident, charming people I know neither smoke nor wear sunglasses habitually. And–(gasp.)–they don’t listen to jazz. So…?

  44. If picture # 5 is any indication, a coat made of stonewashed denim cloth is cool.

  45. its both the cloths and who wears them.

  46. A.E.W. Mason | November 15, 2013 at 3:23 pm |

    Ten suggestions for follow-up posts in the form of a question:

    1. Is “cool” stupid?
    2. Is “cool” contrived?
    3. Is “cool” a sublimation for the lack of substance?
    4. When has one achieved total “cooliosity”?
    5. Is “cool” the proper subject of your Berkley PhD. dissertation?
    6. Was the Boeing B-29 Superfortress “cool”?
    7. Is it “cool” to aspire to “cool”?
    8. Is it “cool” to discuss what’s “cool”?
    9. Was dueling “cool”?
    10. Is it “cool” to smoke a cigarette, turn your collar up and knit your brow whilst contemplating your future condiment empire?

    By the way, I thought momentarily that the emjkmj vs. AEV controversy had the potential to be Ivy Style’s Buckley vs. Vidal moment. Now, that would have been “cool.” Alas.

  47. Please, no crypto-nazi name calling cool?

  48. #6 and #9:

  49. A.E.W. Mason | November 15, 2013 at 7:56 pm |

    DCG: Agree.

  50. At 19, shortly after taking up fencing, I was involved in something duelish (pain and lashes involved) at the Renaissance Faire. Pretty intense experience. I’ll have to tell you the story sometime.

  51. I don’t know if a B-29 was cool. I don’t know how it was in the Pacific, but relatives who had been there and done that in Europe always told me that the bomber guys were not the cool kids (though they were often the bravest kids. You had to be pretty badass to hold course without flinching when the Luftwaffe showed up.) The cool kids flew fighters.

  52. A.E.W. Mason | November 16, 2013 at 1:50 pm |

    My son was a fencer until he was about 19. He was pretty good. Love to hear your story. Are you referring to the Renaissance Faire here in So. Cal.?

  53. No, Northern California. Was held in Novato, I believe.

  54. Orgastic future | November 16, 2013 at 4:57 pm |

    A.E.V challenge: Go at least 5 articles without mentioning Fred or Unabashedly Prep.

  55. A tedious obsession with cool
    Is the infallible mark of a fool;
    Jazz music bores
    And dark glasses indoors
    Should be avoided at all costs.

  56. Somewhere there’s an Ivy Style article asking the question What Kind of Ivy Are You? Or something like that.

    Best I recall, CC presented three options: cool, elegant, and, if my memory serves, traditional. I think the first was a hybrid of 60s era-hipness and circa 2013 hipster cool. Elegant: okay, I forget. The Traditionalist, likely Southern, takes inspiration from 80s-era Brooks Brothers: a sort of Preppy/Trad hybrid. (am I getting any of this right?)

    Hipness is just too hard for me. “Is this hip?” Just too much work. Trying for elegance doesn’t feel right, either. I could be wrong but a certain overbearing neatness undergirds both.

    But Traditional–not only does this resonate with me, I think it’s probably where many if not most sack jacket, striped repp tie, OCBD-wearing men locate themselves. There aren’t many of them. A lof of the better known devotees of the look (P.J. O’ Rourke, George Will) came of age in the 80s. Or at least bought a lot of their clothing then.

    If Charlie Davidson likes to use the word “Cool,” I have to believe he’s not entirely opposed to “traditional.”

  57. Another obvious one is Tucker Carlson. No one would say he’s doing the hipster or 60s-era hip thing. Yet, it seems he consistently prefers sack jackets and suits and repp and club ties. And loafers. I’ll guess–and this makes sense when one considers his age–he garners a fondness for 80s Prep. Most of it, anyway.

  58. SE
    How did G. Will come of age in the 80s, in 1980 he was about 40 years old. He would have started Princeton before 1960.

    P.J. O’rourke most likely changed course some time in the 1970s. He was born in 1947, so college mid-sixties Ohio, he was a self described leftist hippie.

    Tucker? don’t know anything about him.

  59. For O’ Rourke I’d bet it was either late or post Lampoon years. Pre Bachelor Home Companion, for sure.

    As for Will: wrong about the dates. he wasn’t a Princeton undegrad. I think he finished his doctorate in ’69 or maybe ’68.

    He was a liberal Democrat. While at Trinity, co-chair of Trinity Students for Kennedy.

  60. I didn’t bother to read all the preceding comments, so this may be redundant.
    Picture #1 is approaching an abomination: No collar roll; Even worse- that padded
    shoulder. Not Ivy, period. I was there, Cornell ’62. I shopped at Brooks, John Lewton,
    Ithaca, NY, Chipp and Paul Stuart.

  61. Roger, I believe you’ll find this post very interesting, and the comments even more so:

  62. Scotch & Soda | November 26, 2013 at 8:23 pm |

    Yes, let it be said that Ivy is as cool as Cool gets. The “uniform” is purely about style, and there is no question that the trappings are flattering to the male and female form alike. Ivy is a projection beyond mere clothing, which defines the very street address of Cool. No cigarette required.

  63. AEV, you got blocked by Fred sun!?!? thats hilarious, I just thought you stopped showing up. And uhhh let go of the hate on FEC, its only a website.

  64. Cigarettes are never, ever cool.

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