Alex Bilmes on how to do preppy right this autumn

Polo shirts, chinos, boat shoes… The preppy look is having a resurgence, says Alex Bilmes – without the sweater slung over the shoulders, thankfully

The Official Preppy Handbook was first published in 1980. It celebrated (and also poked fun at) a way of dressing, and indeed living, that had been established for decades at elite US universities. The fetishising of the smart-casual lifestyles of well-to-do college kids continues to this day: 40 years on, preppy is a defining menswear code of 2020 – not just Over There, but here, too, where boat shoes, turned-up chinos and colourful polo shirts are once again objects of desire not only for the comfortably middleaged, but among the cuttingedge jeunesse dorée.

Fashion’s chin-stroking sociologists will no doubt diagnose multiple psychopathologies behind this development. But there’s no great secret to it: in this discomfiting year, what could be more appealing than slipping into one of the most approachable styles of the pre-covid 20th century, a golden age when everyone was attractive and wealthy and nothing went wrong?

The zenith of preppy might be thought to be the early ’60s, when preppy icon JFK was in the White House. It’s had its moments in the shade since then, but the look staged a comeback in the ’80s, when tasselled loafers were pressed to the pedals of Porsche convertibles without a hint of irony, and adolescents wore blazers without being bribed to do so. And it’s this version that has made an unscheduled return, revving its engine like the chiselled villain from a teen movie, a pastel sweater tossed over its shoulders like a cashmere cape.

Among menswear aficionados, the new-look preppy is referred to as neo-prep, or prep 2.0. This suggests a major overhaul when, in fact, it’s just had a refresh. A new class of labels offer a slightly bolder take on the established essentials: slogan sweats, rugby shirts, buttondowns, polos, chinos, stripes and checks. Just a few of the young names making the running: Noah, Aimé Leon Dore, Rowing Blazers, Ami, Maison Kitsuné.

I think a bit of preppy, old or new, is just dandy. One doesn’t want the name of an American university one has never visited, let alone studied at, emblazoned across one’s chest, but a smart sweatshirt worn over a buttondown, chinos and loafers: what’s not to tolerate?

A note of caution to the preppy Brit: the aforementioned pullover slung over the shoulders is the sort of thing best left, old sport, to our Gatsbyish cousins. Even if you graduated summa cum laude from Yale, you can’t expect to get away with that. Alex Bilmes is editor-in-chief of Esquire

Fashion editor Simone Marchetti seen at Milan Fashion Week in February

Matt Damon, Jude Law and Gwyneth Paltrow in The Talented Mr Ripley (1999)