How Preppy Is Too Preppy?


In the name of JFK, Paul Newman, and Ralph Lauren, amen. Praise be to the holy trinity of prep. May we, as they, loaf with ease in white sock and chino, in oxford-weave, varsity cotton and cable knit. May our athletic club colors light the way, and the sun of an endless Hamptons summer warm our backs.

No? Just me?

I caught up with one of the high priests of prep this week. Jack Carlson is a former cox of the American national rowing team, turned clothing designer. He represented Oxford in the Boat Race and his country at the world championships, so it’s safe to say his prep credentials are assured. He runs a brand called Rowing Blazers, which began by making blazers for rowing clubs (duh), but has since evolved into the outfitter to aspiring prep-lords across the world. Button-downs, slacks, rugby shirtssignet rings; RB does it all. There are block-color baseball caps with phrases such as ‘Archaeology Club’, ‘Byzantine Art Club’ and ‘Finance’ stitched across the front. There are even Pierce & Pierce gym bags, made in honor of the most depraved prepster ever conceived, Patrick Bateman.

I love it all. I love the colors, the energy, the irreverence, the Americana. But I worry that I only love it in principle. When I met Carlson he was wearing RB’s new ‘Spring Squall Sailing Jacket’, made in collaboration with Land’s End, one of the great institutions of American prep. (You could lump it in with Gant, J Crew, Polo, for example.) I had seen it already, and nearly bought it (just $99!), but I wondered how the primary-color patchwork of the jacket would translate to London, so my basket stayed empty. Of course, it looked great on Jack because he was an actual rower from actual America. There’s authenticity. But what about me? I’ve never sailed and I only ever row at PureGym.


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At Aime Leon Dore, another New York brand that has just unveiled its SS20 collection, the prep is approached from a more sporting angle. Sweats are chunkier, colors are dustier and the overall vibe is kind of Seventies, kind of Nineties, kind of outdoorsy, kind of diamond-geezer-at-leisure. Tony Soprano on a fishing trip, maybe. They deal in the preppy classics – Harrington jackets, patchwork shirts, cardigans etc—but do so with a bit more edge. It’s still easy and irreverent—Lesbos fishing village knitted into a sweater, anyone? – but it’s just slicker. (One very strong piece of evidence for ALD’s slickness lies in the recent collab with Porsche.) Perhaps that’s more my scene, but should I be a US prep-lord or stick closer to home?

Drake’s, who worked on a capsule collection with ALD last year, does the best line in British prep, if you ask me. I normally stop in and see the gang at Pitti Uomo in Florence, the second stop on the biannual fashion jaunt around Europe. This year Drake’s stand was four times bigger than that of the season before, but it was just as jammed a with cool, sartorial dudes as usual. In what seems like a very short time, Drake’s has moved from venerable men’s outfitter with a slightly kooky vibe, to de facto outfitter to all discerning eccentric prep-lords across the globe. Big in Japan (a very good sign), the shtick at Drake’s is one of a sexy college professor with an eye for Neapolitan tailoring, a penchant for edibles and a Vespa. The sportswear is the latest Drake’s revelation. Track tops, ruggers, jersey sweats, pique polos and the like. All in the color palette it takes to scrap in the prep octagon; all the build quality you need to hold your own at Pitti Uomo.

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But again, can I go full Drake’s? In the look book, the young dudes often have sweaters tied around their wastes or looped carefree across their shoulders. Is that OK, or a touch… much? One lad wears a shirt and tie under a polo shirt under a blazer. I don’t think it’s right, and yet there’s nothing I want to do more.

I've considered the cowboy trend, but I don't have the bum for chaps. And my feet are too big for those Bottega Veneta Chelsea boots everyone's wearing. So, no, it’s fine, I’ll go full prep-lord for Spring 2020. Now, who’s my house captain? Where’s the Sorting Hat?

This story originally appeared on Minor edits have been made by the editors.

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Charlie Teasdale
Esquire Deputy Style Editor
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