Preppy Clothing is an Upper-Middle Class Staple. It's Also Becoming a Costume.

In 1676, a young woman named Hannah Lyman was hauled before a Connecticut court for wearing a silk hood despite not possessing an estate worth more than 200 pounds (about $350,000 in today’s dollars depending on how you do the math). She was found guilty under colonial sumptuary laws inspired by the English Act on Apparel passed in 1363, which forced men and women to dress according to their station. The act was not just meant to check vanity. It was meant to check a mercantile class on the rise after the Black Death destabilized Europe’s caste system by wiping out half the population. In America, mercantile from its inception, these laws quickly ceased to be enforced. But they didn’t disappear. They became the basis of our style bibles.

During the 20th century, Esquire, Vogue, and GQ – magazines that began as trade publications – offered middle class Americans dizzied by their own upward mobility style advice in the form of dictates: Don’t wear brown in town. Match your leathers. Never button the bottom button. These rules were less who than how. They assumed anyone could wear anything so long as that anyone knew what to wear it with. The coverage focused on fancy people dressing simply and simple people dressing fancy because that spoke to a national sense of solidarity and because it allowed Condé Nast to reach a broader audience. The result was that so-called preppy clothes casually worn by circumspect elites became the core of the American wardrobe – the heritage of a democratic people.

Preppy is an aesthetic. Heritage is an idea – it describes a continuity of behavior, manners, and obligation that outlasts individuals. Where “preppy” describes clothes, heritage describes the experiences of the people who wore them. But as the core ideas that imbued those clothes with meaning — modesty, sure, but also civic responsibility – were undermined by a wildly successful half-century economic war on the middle class (including the upper middle), heritage had to be replaced with something untethered to history: synthetic heritage.

Synthetic heritage is what happens when products derive their appeal from connection to an invented rather than real past. Invented or implied histories allow brands to market a sense of cultural continuity to broader audiences by implying commonalities that maybe don’t exist. The trouble is that real life has a tendency intercede and expose that there was nothing to belong to in the first place. This kind of marketing has allowed many of today’s most successful brands – Aimé Leon Dore, Buck Mason¹, and Sezane to name a few – to fill the preppy holes in the middle-market. But it has also made those brands dependent on a stories about America that ring increasingly false. That’s why tomorrow’s most successful brands – Sporty and Rich, Parke – are getting into the business of parodying if not outright roasting J. Crew.

For at least one brand (J. Press) it’s kind of a revenge tour.

The O.G. preppy schmatta model was simple: Sell simple clothes to fancy people. Brooks Brothers, founded in 1818, clothed the new professional class in modest luxury – sack suits, dark blazers, white Oxfords. Abercrombie & Fitch sold the same people hunting gear that matched their boots from L.L. Bean and shirts from Gant. J. Press, founded near Yale in 1902, replaced gowns and caps with tweeds and flannels. These businesses were all effectively outfitters selling context-specific clothes to a circumspect elite. Real preppy people. Then they got ripped off by an entrepreneur in New Jersey going after a bigger market.

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