In the course of its journey from the playing fields of boarding schools to the streets of the 21st century, the way of dressing that we call “preppy” has evolved from a simple sartorial expression of knowing nonchalance into a hundred various ideologies of style. Sometimes a pair of penny loafers is just a pair of shoes; sometimes it is an emblem of social privilege or a signal of political conservatism. This fall, the shoe—and the whole wardrobe for which it stands—is a symbol subverted in collections that offer trad with a twist.
In recent years, a wave of New York streetwear brands has democratized and deconstructed preppy threads to sensational effect. Labels such as Noah (with its bucket hats and logo tote bags) and Rowing Blazers (with its jaunty rugby shirts and playful accessories) repurpose prep staples as cool-kid casual, and there’s an inside-jokiness to the dad-hat graphics and fun-shirt constructions. But it is an inside joke that invites all listeners to laugh. Their vibe isn’t exclusionary. Everyone is invited to hang at their country club.
This last point is crucial. The problem with prep, particularly at a moment where the culture is addressing structural inequality, is its Social Register pedigree, its connotation of teen-comedy villains in Lacoste tennis shirts and sloppy-drunk frat boys in critter shorts. Thom Browne may be the master of upending (and upcycling) the clichés of this arena. His shrunken suits and tongue-in-cheek turns on golf and tennis gear have garnered accolades for years, in part because of his studied take on traditional menswear—his ironic distance when reworking the meaning of the clothes as uniforms. It matters that Thom Browne, like Ralph Lauren before him, espouses a racially diverse vision of prep. There’s precedence for this: In the 1950s, Miles Davis made the Andover Shop—the kind of Cambridge, Massachusetts, haberdashery where an economics professor might order his tweeds—a must-stop for Black jazz stars. The new prep is all for that, and for evolving a more inclusive aesthetic.
Consider, for instance, the preppy-infused pieces now on offer at Gucci. Historically, the chief connection between Gucci and adherents of The Official Preppy Handbook has been the bit loafers worn with everything from evening suits and Wall Street pinstripes to chinos. This fall, creative director Alessandro Michele imbued his collection with an added dose of edgy prep energy. Vivid tattersall prints worthy of a hipster’s hunt club sit alongside dizzying checks and saturated tennis-lawn solids. The style is so bold as to achieve an elegant punkishness. Similarly, Miuccia Prada, by experimenting with the proportions of sweater vests and corduroy jackets and by reimagining Fair Isle patterns as pixelated expressions of a digital age, has generated a vision that is both urbane and futuristic. Think Wes Anderson outfits adapted to a Blade Runner world.
Meanwhile, younger designers work to evolve prep dressing into a sartorial philosophy to be appreciated in new corners across the globe. Kenneth Ize is among the most exciting of the group. American prep has always looked abroad for inspiration—as with the madras prints and khaki trousers taken from India—and Ize, who was raised in Austria by a Nigerian family, designs clothes that talk back to that history and bring the cross-cultural dialogue into the globalist age. This year, during his debut at Paris Fashion Week, his sharply elegant jackets and coats beautifully blurred the distinction between traditional African prints and old-school yacht-club plaids. He earns an A for reappropriation.