The Preppy Costume Days Are Over

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

35 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. Just looks like another urban “glee” fruit

  9. 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,

  10. 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.

  11. 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.

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


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

  13. 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.

  14. 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.

  15. 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.

  16. 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.

  17. Thank god. Someone should forward FEC at Unabashedly Prep the memo…..we have him, in part, to blame for the costumization…..

  18. “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.”

  19. 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?

  20. 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.

  21. 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.

  22. 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.

  23. Christian | June 4, 2012 at 10:23 am |

    Lovely image, MAC, thanks…

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

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

  26. 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.

  27. Looks like that clown from WASP 101

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

    Nope. Not fat enough to be Richard.

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

  30. 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.

  31. 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?

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

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

  33. 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.”

  34. 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.

  35. 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.

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