Are You A Twentysomething’s Romantic Nightmare? T&C On Preppy Boyfriends


Today Town & Country’s website posted a humorous piece aimed at female readers that dissects the no-less-than-six distinct types of preppy guy that a preppy girl is apt to date in her twenties. Apparently by 30 she’s either had enough or actually gotten hitched with one of them.

You might find the piece’s sartorial and educational micro-distinctions amusing.

It’s worth noting that there are seven guys in the above photo that T&C chose for the piece, so either there’s doubles on subspecies or the article skipped a type. Perhaps the OPH’s category of “aesthete.” — CC

Photo by Neil Rasmus/

45 Comments on "Are You A Twentysomething’s Romantic Nightmare? T&C On Preppy Boyfriends"

  1. How, exactly, do these guys differ from bros?

  2. Henry-

    There is a difference, but it is hard to articulate, and the two groups certainly share space on a Venn Diagram. And for a time, during college, the lines do tend to blur to the point of being invisible.

    AEV- you’re spot on with your observation about T&C’s tackiness in writing for an audience of women looking to secure wealth via a man. I’d hope that any modern “preppy” women reading that rolled their eyes as well.


  3. Straight Arrow | February 25, 2015 at 12:20 pm |

    The chinos on the guy in the middle have a ridiculously high crotch and ludicrously low waist. And this passes for ivy/preppy style?

  4. S.Arrow- It’s just the trend in clothing manufactures. Not preppy, but easily available.

  5. Who said it passes for Ivy/preppy style?

  6. @ Straight Arrow

    Yes, it appears that our man is still in diapers.

    I lost interest in the inane piece halfway through reading and was not able to continue.

  7. I might add that the subject of this article should read A**holes by Aaron James :

  8. Photo of the bros aside, I thought this was funny and forwarded it to some girls I know would find it humorous. It’s satire guys.

  9. Satire is a sub-strata of society saying, “You can’t make fun of us as good as we can.”

    T&C always has been and will continue to be a nouveau rag. C. Amory’s “Who Killed Society” chronicles how dreck filled glossies like T&C ever became popular in the first place.

  10. I’d get my daughter a chastity belt before I let her near any of those guys in the photo.

  11. I’m always forgetting to give Daddy back his Rolex.

  12. @AEV you and I may be on opposite sides of the political spectrum but I could not agree with you more on this.

  13. Straight Arrow

    You are correct, the guy in the 501s is wearing the highest rise pant. 😉

  14. I wonder how these guys dress when not in their rowing blazers? (Harvard on right, Princeton second from left, and I think Leander in there too).

    Today, I think any young woman would be lucky to grab a preppy man — of any ilk. In a degenerating society like ours they can only do worse.

  15. Funny piece, in my opinion.

  16. Good gosh. AEV nails it. What he said.

    The Southern version is flawed. How did they include Elon, which is essentially a satellite campus of Rutgers, and fail to include Sewanee, Furman, Ole Miss, and Rhodes?

  17. Can I just say – and not just from the multiple mentions in the T&C article, but everywhere and all the time – that, now firmly in my 40s, I could not be more glad to have missed the Barbour trend?

    First because, legacy be damned, they are currently appear to be a hot item centered entirely within a certain 20-something/early 30-something “aspirational” group; and

    Second, because, I cannot see them on a male person and think they look anything but effeminate. Can’t put my finger on why, but I do. Like those Prince Albert slippers you see a certain type of guy wearing these days.

  18. @ Paul: Barbour jackets are unbecoming and unflattering to 90% of the people who wear them. The jackets have a certain utility in the country but, contrary to what people imply on preppy and preppy-like blogs, 98% of us almost never set foot in the country (suburbia is not the country). People wear Barbour jackets, I believe, to impress other people who wear Barbour jackets. “Look at me in this ugly jacket. You know what it is and how much it cost. I’m so special, am I not?” The Barbour jackets look especially ridiculous in Manhattan where they are not suited to anything.

    And I think that one should not wear velvet slippers outside of one’s own home.

  19. Wait, what are we talking about here, quilted Barbour jackets? Are/were these trendy (along with LL Bean boots)?

    I see them on old men of the Upper East Side all the time.

  20. I once went to the Barbour website, and the only jacket I saw that I liked was something called the “Sapper Jacket”, which looked bad-ass: like something you’d wear in the SAS.

    I suspect that neither the 20/30-something “aspirational” crowd on the preppy blogs, nor the UES crusties, are trying to look “bad-ass”… or even know what the SAS is.

  21. They even have the Sapper in waxed camo. If you wear that, you’re basically saying, “I used to poison people’s toothpaste in Rhodesia … when there was a Rhodesia.”

  22. Paul & JR,

    I’ve been wearing the Barbour Bedale model for 20 years. I love it. It’s wonderfully made, classically styled, and works in town as well as the country. Just because you don’t like it (which is fine, its all about personal style and opinion) doesn’t mean you need to make judgement calls of those who do. Do you know how stupid you sound with your pseudo-psychological profiling? For god sakes, out of all the crap people wear, you’re going to mentally shit on people you pass on the street who wear “Barbour coats”???? Assholes, both of you.

  23. Charlottesville | February 27, 2015 at 11:17 am |

    Paul — I also tend to dislike fashion trends involving what had been traditional items of dress, although I don’t get the effeminate vibe from Barbour jackets that you do. I got mine in England in 1990, and at that time I didn’t see them often in the US, certainly not for general street wear. Now, like Burberry, they are trendy and even come with the company name stitched on the outside. My ancient version, sans external logo, is a bit frayed, and in bad need of a thorough reconditioning, but I still drag it out from time to time. I wore it last week to shovel snow, and found it serviceable. Rowing blazers (whether earned or not) also seem to be a trend. I didn’t row, and so will never wear one. And just this week I read in the WSJ that Hunter wellies are a fashion must, and are available in bright colors, some two-toned or patterned. I can attest that the local 20-something girls seem to don them every time there is a sprinkle of rain but, while I live in the country, I have not found that the mud at my place is sufficient to merit the acquisition of rubber knee boots. What next, I wonder. Christys’ bowlers in stripes? Denim Norfolk jackets? One can harrumph, I suppose, or simply smile. I tend to do a bit of both.

  24. @ Charlottesville: We’re on the same page – Bean Boots are also trending right now with the “local 20-something girls”; but I got mine 20 yrs ago, treat the uppers every year, and they are my go-to turkey-hunting and show-shoveling boots. I don’t wear them to happy hour.

    @ Ethan: I wasn’t judging you, I was bemoaning the trend (which, as a long-time owner/wearer, I might think you’d join me in). Instead, ironically, your post makes you sound pretty much like the guy JR was describing.
    Ultimately, though, as you say it’s all just style and opinion. No wrong answers.

  25. I prefer to sleep under a quilt rather than wearing one on the street.

  26. Paul,

    What upset me is making judgements on the those who wear them, without knowing the person. It’s snobbish as well as petty IMO. Personally, I want more people dressing in the classics, whatever their motive may be. It helps keep the companies in business making them, and encourages more companies to produce classically inspired clothes, plus they look better. I don’t have any psychological need to be/feel “exclusive” in my attire.

  27. @ Ethan: in my view, the 20/30-something wearing it “aspirationally” is a different animal than the life-long customer. I’d think that, as the latter, you’ve probably earned the right to roll your eyes at these kids who are going to throw their jackets in the back of the closet 18 mos. from now when the next trend comes along. Although, as you say, if it keeps the companies alive …

  28. Charlottesville | February 27, 2015 at 12:15 pm |

    Ethan — Hope I gave no offense. I confess that I am sometimes guilty of judging by appearance, but the characteristic is a nasty one, and I try to catch myself (looking askance at trousers without cuffs is a particular nonsensical bugaboo of mine, and let us not even think about gym wear and worse worn on the street). For the record, my Barbour is the waxed cotton type, not the quilted version, although my wife has a knockoff quilted vest from Talbots which, worn with a sweater, is very fetching in my opinion. I also have a quilted vest, but it is the conventional down-filled sort from Lands’ End. Incidentally, it works well under the Barbour coat if it is especially cold. That said, I have no quarrel with the quilted Barbour, for man or woman, and think it fine for strolling on the UES if one is so inclined. And Paul, I too am a fan of my Bean Boots, which have come in very useful during the recent snowfalls.

  29. Paul,

    First off, I’m sorry for calling you an asshole. Secondly, unlike some people, I don’t feel there’s a sartorial caste system… Dressing “aspirationally” esp in your 20’s is expected if not encouraged right? “Dress like the man you want to become” and all that Dickensonian stuff. Dressing well, even aspiring to elevate yourself, isn’t the same as making up a fake story of who you’re, or where you come from (We’ve seen enough of that on preppy blogs).

    Next time you see someone in there 20’s dressing “aspirationally” compliment them, maybe that nice item won’t see the back of the closet 18 months later… 😉

  30. “Missing the Barbour trend” is like missing the bow tie “trend” or the L.L. Bean boot “trend.” There are many, myself included, who’ve been wearing these things for decades without giving a damn whether or not they’ve cycled back in fashion with bandwagoneers.

    I also couldn’t care less if my Border, Northumbria jackets are flattering–they transition from hunting to happy hour flawlessly, even with multiple patches and repairs. I like the fact that they’re so obviously old, and I cringe every time I see someone with a flawless jacket and shiny new Barbour collar pin.

  31. @Ethan: apology certainly accepted. And that’s a good point: maybe by receiving a compliment, a young person will start the migration from “trends” to classics.

  32. @AnotherDave: re: patches and repairs, my wife is sick of hearing me complain about off the rack broken-in, and frayed, chinos and how “when I was young” you had to ‘earn’ your broken-in pants by starting out with stiff as a board Duck Heads, and only after a year or two did they achieve perfection.

    Which, ultimately, is probably over-thinking your pants.

  33. I often wonder what some of you would think of me if you passed me on the street. I’m 32 and have been dressing in a relatively traditional manner since I could reasonably afford it, both monetarily and socially. For years my job denied me the ability to dress professionally, thus my leisure time wardrobe was the only place I could go to look my best. My mood and my wardrobe seem to mimic the seasons here in Ohio. Winter is cold, drab, and usually reserved for navy blue, grey, and more grey. Summer is bright and fun, thus color is necessary. If you saw me in July, wearing bright yellow pants and a lime green polo, would you regard me as just another wannabe preppster, lost in a sea of Millennial twits? Because when I get the rare occasion to feel the sun on my face I want to celebrate, both through attitude and through my clothing. Am I alone in this?

  34. @ Mr. Watchman

    I praise you for wearing traditional attire, and everyone else, who thinks dressing up is more than a clean t-shirt and jeans.

  35. Watchmen, I’m with you. I, too, like to celebrate the seasons in my clothes. Autumn sees fabrics such as tweed, corduroy, flannel, and Oxford cloth, colors such as green and brown, and patterns such as plaid, tattersall, and game birds (for ties). Winter continues the trend, with lots of navy and gray.

    When spring rolls around, pastel pink and yellow, as well as pale green, make their way into the rotation. The plaid wool and game bird ties get put away, replaced with ties in brighter colors and seasonal fabrics, like mogador and raw silk. The segue into summer sees linen, seersucker, white ducks, white bucks, cotton ties, madras cloth, and other joys of summer clothing getting their days in the sun.

    So no, I don’t think you’re alone in this.

  36. “I see them on old men of the Upper East Side all the time.”

    So, they’re firmly New Money, then?

  37. “of” the Upper East Side? “of”? Seriously?

  38. Charlottesville | March 2, 2015 at 1:03 pm |

    Watchman – I will be right there with you come summer weekends, wearing light blue or pink oxford cloth or seersucker pants, Nantucket reds, white ducks or perhaps even what a friend calls my “clown pants” (i.e., patchwork madras), all with cuffs, of course. They work with penny loafers, bucks or Topsiders, topped by a polo or ocbd, under a navy blazer or not, and all say SUMMER. Glad that you, like our frequent commenter OCBD, are keeping the light burning in Ohio.

  39. Malvernlink | March 4, 2015 at 11:54 pm |

    Gentlemen possess charm and a sense of humor. Many of the above commentators have neither. Only the painfully insecure could read so much into what was just a humorous tongue in cheek article.

  40. Haha! I found this great. Thanks.

  41. @ Malvernlink:I will agree. It’s a shame, really. The seriousness towards the article is telling.

  42. Gentlemen also possess “a coat of arms and some landed property”, to quote C.S. Lewis, but I imagine (could be wrong) many of us have neither.

  43. James Dalessandro | December 29, 2021 at 6:34 pm |

    I’ve noticed the diversity in the group picture?????

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