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.

“J. Crew was the first truly synthetic-heritage success story. Founded in 1983 by mail-order mogul Arthur Cinader as a riff on J. Press – down to the stolen initial – the brand got traction by selling roll-neck sweaters, barn coats, and rugby shirts to customers in Shaker Heights and Naperville who wanted to look like Yalies on break in Nantucket (and had no way of knowing what that actually looked like other than catalog photoshoots). The aesthetics weren’t new, but the distribution was and Cinader’s daughter proved superlative at spotting designer talent so the clothes quickly got good. Before long, upper-class people were actually dressing down in J. Crew. The lie at the center of the brand stopped being a lie and became what French philosopher Jean Baudrillard called “hyperreality.” His description of this phenomenon will ring true to anyone who gets the catalogs:
“Disneyland is presented as imaginary in order to make us believe that the rest is real, when in fact all of Los Angeles and the America surrounding it are no longer real, but of the order of the hyperreal and of simulation. It is no longer a question of a false representation of reality, but of concealing that the real is no longer real, and thus of saving the reality principle.”
It’s all terribly French, but the long and short is that at some point the catalogs ceased to show how students dressed and began showing students how they ought to dress. Fantasy became the critical reference point. The synthetic heritage model – sell simple clothes to fancy people and fancy clothes to simple people – took off.

In 2017, J. Crew transferred about 72 percent of its trademarks to an offshore subsidiary to use as collateral for new debt. In 2020, the company entered Chapter 11. What led to the collapse? Fast fashion, sure. But something more significant as well: The Great Recession. In the late aughts, many middle- and even upper-class Americans lost faith in the idea of a collective identity. The point of getting dressed was no longer meeting in the middle. Prep receded.2
The imagined world ceased to be hyperreal and became hyperfake.
Many shoppers moved on to brands engaged in different synthetic heritage plays. ALD does this by creating a fictionalized Seinfeldian universe rooted in Queens. Buck Mason does this by imagining there was an Ivy League school in California3. Because the locus of women’s fashion in Paris, not New York, Sézane sells a fantasy of cosmopolitanism rooted that owes its entire aesthetic to 1970s French cinema and study abroad.
This is not to say that these clothes are bad – just that brands are delicately positioned because they have positioned themselves as outfitters selling context-specific clothes to a circumspect elite and that elite doesn’t actually exist. It’s the J. Crew trick minus the differentiated distribution and inevitably creates a kind of cognitive dissonance. Emily Oberg, founder of Sporty & Rich, seems to understand this innately.
Sporty & Rich doesn’t engage in any form of synthetic heritage. Its $155 hoodies read “Wellness,” “Health Club,” or “Athletic Department.” The slogans are so broad it’s parodic: metadata as branding. What’s interesting about Sporty & Rich is that it has the integrity to tell baldfaced lies, selling merch for non-existent institutions. But no one thinks the “Beverly Hills Riding Club” really exists. For precisely this reason, the brand can sell aspirational clothing without forcing shoppers to buy into a fiction (or submit to a hyperreality).

Admittedly, this is a kind of silly approach, but it’s also democratic (anyone can join a club that doesn’t exist) and honest. Like the EBITDA dad hat or the NFL logo cap Rob Lowe wore to a playoff game, Sporty & Rich states rather than implies. It admits to the hollowness at the center of the modern American project that J. Crew tried to hide. We crave a sense of belonging and shared purpose our institutions no longer provide. We do not share experiences. We only share aspiration.
The same baldfaced simplicity powers PARKE, Chelsea Kramer’s viral sweatshirt label. Her $125 mock-necks embroidered with PARKE across the chest routinely sell out in minutes. There’s no school, no alumni, no continuity. Parke sells the comfort of a transactional admissions process. It’s young fans don’t know if they can get into a good school (probably not), but they can buy a sweatshirt.
Last year, Jack Carlson – founder of Rowing Blazers, the maximalist prep label that turned Oxbridge crew-team heraldry into unlikely retail success – became creative director at J. Press. Carlson isn’t just a democratizing designer; he’s a designer almost wholly uninterested in the how of clothing. After all, no Oxford student who didn’t row for the Merton College Boat Club would ever wear a blazer embroidered with the team’s crest. (That would be stolen valor – a violation of unwritten sumptuary law.)
One cozy wool sweater from Carlson’s new collection declares “Old Enough to Know Better.” Another has J. Press splashed PARKE-style in varsity letters across the chest. Rather than pretending the world that produced “Ivy Style” still exists, Carlson is playing in the ruins. And that parodic approach is the smart as hell. Carlson’s J. Press isn’t built on a false premise so it doesn’t have to ask shoppers to hold reality and hyperreality in their heads at once. Instead, they can use their clothes to poke fun at reality. They can make it clear to others that they do in fact know better.

There’s an old Swedish saying popular with mom’s who own hiking boots: “There’s no such thing as bad weather, just the wrong clothes.” The weather is still the weather, but the economy has become the climate. Clothes that imply we can – and do – meet in the middle simply aren’t the right clothes. Instead, we need clothes that affirm the similarity of the aspirations we have in common: wellness, wealth, EBITDA, and being in on the joke.
Still, as Baudrillard warned: “It is dangerous to unmask images, since they dissimulate the fact that there is nothing behind them.”4 That danger – the possibility that, if we stripped the signifiers away, we’d find nothing real underneath – is why sumptuary laws existed in the first place.
Hannah Lyman wanted to be sporty and rich.

