The Preppy Costume Days Are Over

We posted this back in 2012. Given recent speculations of COVID’s fatal blow to the way people dress (more on that soon), maybe a preppy costume revival isn’t such a bad thing.

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A few weeks ago Esquire’s Matt Sullivan wrote a piece about his high school reunion. And not just any high school, mind you, but the Collegiate School, evidently the nation’s oldest school.

Sullivan attended clad in the outfit above, which got a mixture of mockery and admiration from his Park Avenue-type classmates.

Later Sullivan chats with Gant’s Christopher Bastin, who says:

The whole preppy costume days are over, which I’m kind of happy about because it’s much more personalized today. The stuff we’re working on is a bit more grown-up, a bit more dressy — dressy but messy, not trying to look like your dad, but not trying to look like one of the guys from “Dead Poets Society” either.

Although Sullivan’s credentials are preppy genuine rather than preppy ersatz, readers will of course respond differently to the outfit pictured above. “You can’t just buy a preppy look off some mannequin in Connecticut,” he writes.

Perhaps, but I’ve seen some mannequins who looked pretty damn preppy, and only needed one go-to-hell item in the outfit to do it. — CC

45 Comments on "The Preppy Costume Days Are Over"

  1. Boston Bean | June 3, 2012 at 8:17 am |

    “In 2007, The Wall Street Journal ranked Collegiate number one in the world in terms of percent of the senior class matriculating to eight selective American colleges.”

  2. Boston Bean | June 3, 2012 at 8:25 am |


    I breathed a sigh of relief because I thought
    the title “The Preppy Costume Days Are Over” was referring to a decision about the future content of your blog. After a moment, however, I realized my mistake.

  3. dude looks like he’s wearing a costume. . .

  4. A snob’s view of how the underclass buy their clothes from a thrift shop. The guy look like a grade A tool, and the pose in the photograph just goes on to prove it.

  5. To clarify my comment – are you taking the piss out of your readers?

  6. I thought the pic was that of the costumes that we was referring to; unfortunately I was wrong. He looks like Urban Outfitters version of a prep.

  7. There is preppy, and then there is buffoonery. A fine line separates the two. Multiple go-to-hell items invoke the later.

  8. Old Bostonian | June 3, 2012 at 8:11 pm |

    One go-to-hell item adds a touch of flair.
    More than one makes one look like a nut case,

  9. Ultra-Orthodox Trad | June 3, 2012 at 8:23 pm |

    The link to the Esquire article reads “preppy clothes for men”.
    A contradiction in terms.
    When boys grow up and become men, they give away their preppy clothes and proceed to Ivy or Trad.

  10. U-O Trad:

    I realize you probably meant that in jest, which is fine, but I’ve come to realize that there are far too many people who actually buy into that no true Scotsman fallacy. I’ve known ancient men who wore yellow pants and bright jackets, and middle-aged boys who obsessed over ivy style.

  11. Ultra-Orthodox Trad | June 3, 2012 at 10:00 pm |


    Not meant in jest at all, sir, not at all.

  12. Old New England | June 3, 2012 at 10:05 pm |


    If we didn’t obsess over ivy style, we wouldn’t be devoted followers of this blog.

  13. Main Street | June 3, 2012 at 10:20 pm |

    Taking an Ivy approach does not simply entail introducing an Ivy element into one’s wardrobe, but rather involves an attitude, a way of comporting oneself.

  14. Old New England:

    I simply mean that a person’s classical clothing choices go only so far toward making him a man. His attitude and character take him farther. Those who shirk responsibility or rely on others to provide for them is more like a child than an adult, regardless of their preference of a natural shoulder. So no, an obsession of ivy does not make one childish (at least I hope not).

    I can see how someone who goes full easter egg may be doing so as to force his personality upon others, that he wants to be seen and heard. The term “go to Hell” has stuck around for a reason: you don’t care what others think about you. That outfit’s attitude may be less in line with qualities that we associate with being a man. However, that’s still a shaky, ad-hoc rubric for such a major accusation.

    That being said, this guy does look like a *raging* jackass.

  15. Old New England | June 4, 2012 at 12:54 am |


    Re: “The term “go to Hell” has stuck around for a reason: you don’t care what others think about you.”

    Not caring what others think about you is patrician, advertising it is plebeian.

  16. “Go to hell” suggests one doesn’t care about how one is viewed by others? Seriously?

    Oh, the irony.

    The effort–the intentionality and self-consciousness–undergirding the above outfit, and the combinations of Nantucket Red and lime green and hot pink and bright yellow one sees among the Try-Harders: it suggests everything but a lack of concern. “GTH” screams “Please, please notice me. Please.”

  17. How should one dress during the summer to display a more Trad/Ivy sensibility than Preppy? Can one wear a pair of brightly colored shorts and yet still appear to be Trad/Ivy?

  18. Christian | June 4, 2012 at 7:10 am |

    I think the main irony of the term “go-to-hell” is that, knowing Tom Wolfe’s style, he likely merely employed it offhand to mean garish.

    Thirty years later it was taken up by the online trad community who took a literal interpretation, either that the sartorial signal was a message that others could go to hell (hence f*** off), or that the wearer was in some way going to hell, or at least his pants.

    But as in Wolfe’s description the clothes are only worn by tribal members among themselves, the message is hardly for other people to go to hell.

    And Hunter, perhaps “Take Ivy” is a place to start.

  19. Collegiate would like to think it is the oldest school in the nation. Boston Latin School was founded in April of 1635. Collegiate conveniently amended its founding date to 1628 from 1638.

  20. It seems this Mr. Sullivan got the response he was looking for, since he wore this attire tongue in cheek, note the article and photo above.

    Question, would the reaction here been as critical if the jacket fit, the pants were a pair of cuffed Bill’s Khakis and the shoes were Weejuns or white bucks?

    Those striped Sperry Topsiders deck? I hope Sperry financially took it up the ass on those.

  21. Agree with MAC, the shoes are horrible. I would have rethought the patches on the elbows. Overall it was a case of poor execution!

  22. Wear that outfit and expect others to take you seriously…Oh wait I am too cool to be paired with my classmates

  23. spudnik99 | June 4, 2012 at 4:28 pm |

    FWIW, I like the shoes, i’d pair with BK shorts, a white ocbd Mercer popover (long sleeves rolled-up), and a navy belt.

  24. Looks like that clown from WASP 101

  25. Not Richard | June 4, 2012 at 7:17 pm |

    Nope. Not fat enough to be Richard.

  26. Richard may be fat and dumb, but he certainly dresses better than this clown.

  27. Chelsea Drug Store | June 5, 2012 at 7:48 am |

    Another clever article from Christian that seems to have entertained some enraged some, confused others and which most definitely will have an unmentionable psychotic plotting revenge.

  28. Ball-crushing pants like that are a learning experience! =)

    Ideally, Ivy Style is comfy and unselfconscious. That’s the nice thing about it, but why does it have to be so hard?

  29. Roomy Khakis | June 5, 2012 at 9:56 pm |

    The penile bulge was never a part of traditional ivy style pants.

  30. This guy needs to join John J. “Skip” Balderdash IV and join The Preppy Anti-Defamation League. Someone will likely beat him up and take his lunch money.

    For more about the Preppy Anti-Defamation League:

    His choice of go-to-hell clothes renders him an over the top preppy cliche — not the hip preppy updater he would like to fancy himself. For more about this, check out “Go To Hell Preppy: It’s Not an Insult.”

  31. Orthodox Ivy | June 8, 2012 at 9:35 am |

    Incredible how people find ways to justify Gay Ivy style by calling it Go-to-Hell.

  32. Dickey Greenleaf | June 9, 2012 at 3:10 pm |

    Ersatz, like me right?, the murmurmer, just kidding, I know my place in the atmosphere, for instance, I think this guy Mr. Matt Sullivan is basically testing the limits here, let’s just say… how far right can you go, or how far left, can you go?, North, South, etc. But style consciousness is never absolutely available in most, or all cases, transparent. Like all great creators, they must think totally outside the box, to make strides in infinite lampoon, in the attempt to provide illumination.

  33. One GTH item per outfit per season. Anything more is unacceptable.

  34. Old School Tie | August 8, 2020 at 1:34 pm |

    Anyway, eight years and one pandemic on….and he still looks like a proper plonker. Nor has that version of preppy disappeared, unfortunately…

  35. Charlottesville | August 8, 2020 at 2:07 pm |

    Aside from the fit, the elbow patches and the shoes, the items above might be just fine individually. But together? Perhaps on a teenager, but I have to agree with those who find the unfortunate costume to look rather silly on a grown man. “Proper plonker,” a new phrase to me (hat tip, Old School Tie), I think sums it up rather well, but to each his own. I know that my patch madras pants draw the same bemused shake of the head from some well-dressed folks, and for all I know they may be right.

  36. When you are “rich enough to drive an old car,” your car becomes a statement of how rich you are. I used to see Charles Pillsbury — whose name was over the door of the company I labored at — show up in an old VW microbus, and wearing a sport coat with the lining hanging out. Chuckie was making a statement we all understood.

  37. Poison Ivy Leaguer | August 8, 2020 at 3:21 pm |

    In his wonderful 1982 parody of the L.L. Bean catalog, “Items From Our Catalog”,” Alfred Gingold referred to GTH trousers as jackass pants. I’ve used the term ever since.

  38. That outfit (the combo and fit) is ridiculous.

    I agree with this:
    “The whole preppy costume days are over, which I’m kind of happy about because it’s much more personalized today.”

    Yes. The traditional, time tested professions will continue to demand either suit or jacket— a grown-up look for grown-up men who actually interact with people, including clients and colleagues. Military officers, attorneys, clergymen, physicians, bankers, etc.

    Let the nerdy, introverted quants waste away in their home offices, staring at computer screens while wearing their jammies…or athleisure equivalent. The rest of us will put on our uniforms and engage the world on face-to face (not Zoom) terms. And thrive.

    Brooks catered to the men who represented the old professions. So did J. Press. So did the men’s stores of old. Little has changed. The math nerds just get paid more now.

  39. Where was the reunion held? On a yacht or at a yacht club? I’m going to say yacht because the club wouldn’t let him in…..

  40. Preppy Finance Nerd | August 8, 2020 at 7:21 pm |

    While I’m more preppy in the spring/summer and more Ivy in the fall/winter, the “one loud item per outfit” rule is one that has saved me more than a few snickers I’m sure.

    While everyone has their own style, I find that guideline helps to avoid *gestures to picture* this. So I mix it up.

    Rocking the horsebit loafers? Maybe go with solid blue chinos and a pink shirt.
    Draping a baby blue cashmere sweater over your shoulders? That’s all the prep I get.
    Rocking the NR chinos? I should treat lightly with the rest of the outfit.

    Also, it’s my first comment ever here on IS! Let my roasting begin.

  41. The panic over “traditional clothing disappearing forever” because of the pandemic is starting to get on my nerves, honestly. Those who’ve always dressed poorly, still dress poorly, and those who’ve always dressed nicely, still dress nicely and can’t wait for social life to come back to normal, to finally start attending formal events. Yes, some companies filed for chapter 11, but those companies had been in trouble before the pandemic, and merely used the situation for their advantage to restructure and make more more profit as the result. Small companies with dedicated customer base haven’t gone bankrupt, large luxury companies haven’t disappeared either. Everything will come back to normal by spring 2021. Let us be patient and wait.

  42. @S.E. – “Let the nerdy, introverted quants waste away in their home offices, staring at computer screens while wearing their jammies…or athleisure equivalent. The rest of us will put on our uniforms and engage the world on face-to face (not Zoom) terms. And thrive.”

    Have you always been a snobby, internet, prick, or have you had to practice at it?

  43. Well said, I.T.

  44. Old School Tie | August 9, 2020 at 2:30 pm |

    Docere – one comma too many. Enough to take any impact away from your response. Also, as far as I am concerned, practice with a “c” is only ever a noun but you may be American, so I shall overlook that for now…S.E. – it is funny you should mention “jammies” because on closer inspection his jacket appears to be made of some sort of fleece fabric. His belt is too thick for my taste as well.

  45. Old School Tie – ha, fair enough on the comma. Alas I am American and used practice as a verb.

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