Forget ‘preppy’ style — I’m team Ivy

To call someone’s style “preppy” can only be, at this point in the history of style, an insult. It evokes a guy named Chad wearing a belt with little whales on it, who looks like the handsome cad in a John Hughes movie.

At the same time, somehow, to say someone’s style is “Ivy” can still be complimentary. The term might evoke, say, the late Sidney Poitier. The best vintage shops from New York to Paris to Tokyo charge through the nose for good Ivy ephemera. Cool brands draw inspiration from it. Serious books are written about it. None of this can be said of preppy style.

The distinction can be hard to grasp. After all, when Chad graduated from his prep school, he went to an Ivy (Dartmouth, I’m guessing). Many individual items cross over between the two — the Oxford-cloth button-down shirt, say, or penny loafers. And the two refer to the same half-real, half-imagined historical period: a prosperous and energetic mid-century America.

How to distinguish the two? Some items can be used to demonstrate a lack of perfect overlap. Critter prints, polos with popped collars and red trousers are preppy, but not Ivy. Harrington windbreakers and cardigan sweaters are Ivy, but not preppy. Nothing preppy about suede desert boots; nothing Ivy about the preppy item with the most contemporary relevance — the dreaded fleece vest.

Preppy style is basically nautical and sporty, like Nantucket. Preppy clothing peaks when it is almost worn out

But the difference between the two styles does not come down to particular items, but to mood or approach. Preppy style is basically nautical and sporty, like Nantucket, and its posture is emphatic casualness. Preppy clothing peaks when it is almost worn out. Ivy is academic, and its posture is a carefully observed if informal tidiness. It is crisp.

The class angle is important. The message of preppy clothes is multigenerational membership in the summer-home-owning class. Those Bean boots are basically Volvos you wear on your feet. Ivy’s class signal is harder to discern, but it is unmistakably more aspirational. Preppy is a legacy admission who takes it all for granted. Ivy is on scholarship, and its shoes show some polish.

The class differences help to explain very different chains of influence. Ivy style has changed, and been changed in turn, by mods and rude boys and punks (as a trip to John Simons’ shop in London demonstrates to this day). It strongly influenced French New Wave style. As Jason Jules and Graham Mach have documented beautifully in their book Black Ivy, it has a role to play in African-American artistic and political culture, particularly in the 1960s. It has mixed easily with the workwear revival and with the trend towards less structured tailoring. It’s Promethean.

The path of prep leads to the commercial empires of Ralph Lauren and Tommy Hilfiger, where it more or less dead-ended a long time ago. I suspect there was nowhere left to go. The posture of satisfied indifference leads to pinched conservatism about new ideas.

Men, as a group, are floundering on the style front. And maybe a certain kind of Ivy style shows a way forward

The distinction is admittedly fussy, and might be of interest only to serious clothes nerds. And my partisanship for team Ivy reflects my own background. I went to a New England prep school (never made it to the Ivies, though, for lack of both brains and connections). I have the same cringey memories of how I dressed in my teenage years as most people do. All those flannel shirts. Those green-collared field jackets. Oh, dear.

But there is a serious, non-clothes-nerd point somewhere here. Men, as a group, are floundering on the style front. Everyone acknowledges this. And maybe a certain kind of Ivy style, or perhaps just the history of Ivy style, shows a way forward. The lessons: drop the posture of indifference. Respect classic style while searching restlessly for ways to make it contemporary. Reject all nostalgia. Be casual and keep it simple — that’s the modern way — while making sure you look sharp and, most importantly, like an adult rather than an overgrown teenager. Put on a sports coat once in a while. Present yourself, not your class status.

The hardest part of that, of course, is the “make it contemporary” bit. You have to care a little bit, spend some time shopping, and try things out. For most men, this can feel like a chore. But reinvention, which is what style is all about, takes work.

Robert Armstrong is the FT’s US financial editor

Find out about our latest stories first — follow @financialtimesfashion on Instagram