From JFK to J. Cole, Preppy style has come to symbolise the American Dream for countless individuals keen to make their mark on the world. What does its latest resurgence tell us about culture today?

Any discussion of Preppy must first begin with Ivy style, a look developed by students on the leafy campuses of Ivy League universities in the 1950s, which mixed collegiate sportswear with elements of Italian tailoring and a dash of Americana. After coming to define the sharpest and most cerebral characters of the ‘50s and ‘60s (think Miles Davis and JFK) Ivy style was absorbed by the mainstream and emerged as the more accessible ‘Preppy’, named after the private preparatory schools whose wealthy alumni embraced it. 

Preppy staples like button-down Oxford shirts, polo shirts (collars popped), cable knits and flat front chinos drifted in and out of fashion in the ensuing years, but when a former tie salesman named Ralph Lauren opened a store on Madison Avenue in 1986, Preppy raised its flag at the heart of American popular culture. 

Bronx native Lauren was not born into wealth himself, but the world he’d created with his eponymous brand was, by his own admission, a way of belonging to an elite society that had seemed out of reach growing up. 

As Hip Hop became a dominant global cultural force in the 1980s and ’90s, Ralph Lauren’s upwardly mobile American dream resonated with rappers from Nas to Andre 3000. It even spawned a subcultural offshoot, ‘Lo-Lifes’, Working Class kids from Brooklyn who’d shoplift copious amounts of the brand’s Polo line to signal their luxury taste. 

And now preppy is back. 

Recent years have seen a vanguard of New York-based brands emerge with their own take on the style. Leading the charge is Aime Leon Dore, founded by Teddy Santis, whose perfect ratio of Upper East Side refinement and Hip Hop credibility became an overnight phenomenon, inspiring LVMH to invest in 2022. Noah and Knickerbocker have also enjoyed success by taking cues from the Preppy aesthetic, with flagships all located in and around Manhattan’s NoLiTa district, birthing a microculture of Oxford shirt and baseball cap wearing poseurs parodied by the NoLiTa Dirtbag Instagram account. 

What does this tell us about culture?

Preppy is more than just an arrangement of clothing, it’s a set of ideas, a toolkit with which to express your view on the world. To a certain demographic, adopting the style of your wealthy parents means upholding tradition and basking in your place at the top of the pecking order. To others, appropriating the clothes of the privileged few is about subverting ideas of taste and Class, proving that you too can enjoy rarified status, regardless of upbringing. It’s a show of defiance. Determination. 

But why now? 

One possible explanation for young men especially becoming drawn to Preppy again is that they are embracing conservatism. Research shows a new gender divide emerging in global politics, with Gen Z men identifying with a more right wing worldview than their progressive female counterparts. Perhaps dressing in the style is, and has always been, a subtle way of expressing approval of the meritocratic, fiscally conservative values of the demographic it’s synonymous with. This certainly rings true in hyper-gentrified neighbourhoods like NoLiTa and Marylebone where you’re most likely to see the Preppy resurgence today. 

BUT, there’s a long-read coming soon on the emergence of young conservatism, so for now we’ll keep it light; the costume parties of fashion continue to rotate through phases of irony, commentary, and straight up affiliation. 

Thought starters for brands

• Fashion is a bellwether. Over the years we’ve come to use a simple rule of thumb to track fashion trends; the ‘bootleg barometer’. Once every twenty years bootleg shaped jeans come back en vogue (the 60s, 80s, 00s, and now) and while it tells us about jean trends, it also gives a good indication of other cycles within culture – and can teach us about nostalgia in music, entertainment, and even food too. So while your brand might have a specific category in culture that it focuses on, you can build out these forecasting models by looking elsewhere. What’s cyclical in your category? And how could you begin to measure those cycles alongside other symbols and signs from culture? 

• More play, less PEST (analysis). While the world is currently embroiled in some pretty hefty issues, we can find levity within culture, and bring a little joy and happiness by being more playful. Fashion does this incredibly well, often making fun of itself as well as the rest of the world, yet a lot of other areas of popular culture never feel as self-referentially funny. Humour and irony can be tricky to execute in marketing comms, but everyone can afford to be a little more playful. Imagine your brand as the jester archetype; what’s next to make people laugh, and bring the world a little joy?

To unlock more insights, email discover@culturelab.co 

^{(Sources: CultureLab CultureIndex, January 2025)}