The Preppy Comeback

This article is part of Upstream, The Daily Wire’s new home for culture and lifestyle. Real human insight and human stories — from our featured writers to you.

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There are a lot of reasons to be excited about Ralph Lauren’s America 250 collaboration with the United States Postal Service.

First and foremost are the “American Icon” stamps around which the collection is built: From Jackie Robinson’s glove to the top of the Empire State Building, these 13 images “celebrate the essence of our country.”

Then, of course, there are the clothes: patriotic hats, polos, and a semiquincentennial edition of the brand’s famous American flag sweater. But most exciting is how Ralph Lauren, both the brand and its namesake, describes the collection in explicitly patriotic language.

“I love America,” Lauren said at the launch of the series, which the brand describes as a celebration of “America’s shared values — freedom, independence, equality, opportunity, and the pursuit of happiness.”

In Commentary this month, Robert Pondiscio laments that America’s 250th anniversary does not feel as celebratory as the bicentennial, largely because we have forgotten our “shared ideals.”

The Ralph Lauren collection suggests that those shared ideals may still have some gas left in them. If nothing else, it means that America’s 250th anniversary, if not as triumphant as its 200th, may be more stylish. Gone are the bell-bottoms and kipper ties we associate with bicentennial kitsch; Americans will greet their country’s quarter-millennial milestone in roll-necks and Oxfords.

America is in the midst of a preppy revival. When Ralph Lauren hosted its first men’s fashion show in 20 years this past January, it was only the latest confirmation of this trend. In recent years, we’ve seen J.Crew claw its way back from the brink of bankruptcy and irrelevance as menswear head Brendon Babenzien pushed the brand back to its classic roots. 

J. Press, the original purveyor of Ivy style, is expanding its brick-and-mortar presence under Jack Carlson, the founder of renegade prep shop Rowing Blazers, who took the helm of the 124-year-old retailer earlier this year. And while European luxury brands grapple with plummeting sales, Ralph Lauren’s revenue is up 10% year-over-year.

What makes this trend especially notable is that it’s being driven by Gen Z, a group not known for earnestly embracing tradition. Menswear industry insider R.F. Kenmore points to the popularity of FX’s “Love Story” and the renewed interest in John F. Kennedy Jr. and Carolyn Bessette as a clear instance of this phenomenon. On TikTok, Zoomers valorize the “quiet luxury” and “old money” aesthetics embodied by the Kennedy clan, a prep rebranding for the social media age.

Kenmore sees the entire trend as “a bit of a reset,” a response to the “era of streetwear … and COVID sweatsuits” from which we’ve just emerged.

“I personally watched, while working at a large American brand, as consumers rotated directly out of booming knits categories such as tees, sweats, etc., and into button-up shirting and woven pants like khakis, driven by both a return to work and a desire to leave those days behind,” Kenmore told The Daily Wire. “The natural swing was into more structured and iconic-feeling uniforms or outfits.”

O.W. Root, a menswear writer and cultural critic, also sees a commercial fashion logic to the preppy revival. Style swings back and forth. Young people who came up wearing hoodies on Zoom meetings want to wear ties; after stuffing themselves into slim-fit suits for most of the 21st century, men have decided to embrace looser, more traditional fits.

But Root sees something deeper going on here, particularly when it comes to young men.

“What many men really ache for, even if they don’t know they ache for it, is style that more or less can be recognizable 10 years from now and 10 years prior,” Root says. “Style that follows them through their life, that roots them in their life.”

“Our clothes are our culture, they say something about our values, they say something about who we are, they say something about what we care about and what we believe,” he adds. “The beautiful thing about preppy style is you can wear it when you’re 17 and you can wear it when you’re 70, and you will wear it slightly differently, but you will still have a recognizably preppy through line through your life.”

Unlike trends, which come and go, and fast-fashion garments, which deteriorate rapidly, classic preppy items are durable, both physically and aesthetically. As Kenmore notes, this has to do with economic realities as much as with a desire for authenticity.

“People are getting tired of rotating disposable crap through their closets and are finally saying ‘enough,’” he says. “This is driving them to buy things that they can have as long as their favorite vintage pieces have lasted.”

But will the prep revival last? Leaf through an issue of GQ and you’re bound to find the hallmarks of early-2000s style — front-zip hoodies and running shoes with boot cut jeans — dotting the pages. If the economy dips, we’re likely going to see a return to mid-aughts business casual — because when money is tight, you need one pair of slacks that can go from the office to the bar.

There are also some concerning signs at the recently ascendant preppy stalwarts. Babenzien, who, as Root put it, “basically spearheaded J.Crew becoming good again,” departed earlier this year. And while he made the brand cool again, that may not have boosted sales enough to keep it out of the red long-term.

Then there’s Brooks Brothers, the pillar of American prep, which recently came under fire for an ill-advised attempt to launch a streetwear line.

“Brooks Brothers is terrible,” Root tells me. “They’ve just — and I hate to say use this language, because it’s so lame, but they’ve just lost their way. They’re not servicing any traditional Brooks Brothers customers at all.”

But these setbacks pale in comparison to the strength of the prep revival.

“Brooks will come back,” Root says. “Brooks Brothers is not going to die forever.” Similarly, Kenmore doesn’t think Babenzien’s departure will materially change J.Crew’s direction. Moreover, as he noted, the Ivy style revival has occurred in large part outside major brands. Today’s preppies care less about flashing their Polo horses and buying the newest collections than about acquiring good, timeless pieces and cultivating a sense of style. 

Americans, it seems, want things that last. Things that matter. Things that connect them to what came before. Prep, like all styles, has ebbed and flowed over the years. But this latest resurgence isn’t just about the clothes. It’s about the attitude. It’s about tradition. It’s about America. And like America, it’s not going anywhere.