When Jonathan Anderson made his debut at Dior in June, the models in his menswear show could just have easily been walking through the Yale or Harvard campuses a century ago. Anderson was all-in on the preppy trend with his modernized versions of Donegal tweed jackets, repp ties, pinstriped oxford button-down shirts and salmon chinos.
But the designer is far from alone as young men globally have embraced the timeless classic collegiate-inspired wardrobe defined by rugby shirts, pink cable-knit sweaters, skinny ties and blazers.
A look from Jonathan Anderson’s preppy-inspired Dior spring 2026 collection.
Giovanni Giannoni/WWD
Preppy can trace its roots to the early 1900s in America when privileged male students at preparatory schools — hence the name — and Ivy League universities showcased their take on the WASP-y, country club look in their Brooks Brothers and J. Press outfits.
While both of these brands continue to be bastions of preppydom, along with such labels as Ralph Lauren and Tommy Hilfiger, they have plenty of company these days as men are turning to companies from J.Crew to Vineyard Vines for the style.
But like any trend, it’s only a matter of time before guys set aside their loafers and argyle sweaters and move on to the next big thing. So how long will the preppy trend last?
“You’ll always see touches of preppy in a man’s wardrobe,” said Todd Snyder. “It’s always in the background.”
For the last decade, it was “street culture” that was prevalent in menswear, the designer said. But a couple of years ago, that started to shift. “It felt like the time was right again. Preppy cleans things up and is a more proper way of dressing.”
Todd Snyder has often leaned into preppy codes for his collection.
Giovanni Giannoni
Snyder embraces many classic men’s codes in his designs, as evidenced by his collaborations with Sperry Top-sider and L.L. Bean, both favorites of the preppy contingent. “And with Jonathan Anderson at Dior, it helps to cascade [the trend] through fashion,” he said. “Others will jump on it.”
Even so, fashion has a short shelf life and Snyder thinks preppy will run its course in a couple of years. “I don’t think it’s a five-year trend,” he said. “But from a cool perspective, it’ll be two years — but it’ll be more country squire preppie.”
Michael Bastian, creative director of Brooks Brothers, the company credited with popularizing many essential preppy pieces such as argyle sweaters, madras, Harris tweed and the polo coats over the course of its 207-year history, is “on fire,” with particular strength in preppy sportswear.
“This goes back about three years to the end of the maximal phase of big logos and branding,” he said. “Then we moved into quiet luxury, but now it’s not so quiet, there’s more color and pattern. Men are responding to sportswear and mixing it with tailored pieces.”
As a result, tweed sport coats, button-down shirts and neckwear have been strong sellers. “Ties are better than ever and it’s all repp stripes, foulards and little critter patterns,” Bastian said. Moleskin and corduroy are also popular.
Bastian said even when other trends take hold, preppy never truly goes away — at least not for the Brooks Brothers customer. In fact, the retailer featured Lisa Birnbach, author of “The Official Preppy Handbook,” in a campaign last year celebrating the 125th anniversary of its invention of the button-down shirt.
Lisa Birnbach, author of “The Official Preppy Handbook,” in a Brooks Brothers ad.
“It catches a wave, but it’s always there when the needle shifts,” he said.
Like Snyder, he believes the needle will continue to point to preppy for another couple of years. “For the general public, it’ll be at least two or three years,” he said.
After that, he expects the pendulum will swing back to “some iteration of street. “In the early ‘90s, there was a nostalgia moment with rugby shirts and early Calvin Klein that was really preppy, and that was a reaction to Lacoste in the ‘80s. Everything is a reaction to what came before.”
Brendon Babenzien, founder of the Noah brand and men’s creative director of J.Crew, said in fashion, “whether it’s the preppie trend, or any trend, we tend to operate on a pendulum swing. When you look at what’s dominating streetwear, it’s youth-driven, outlandish and aggressive so it’s obvious the pendulum will swing the other way and that choice is more conservative, clean-cut and tradition.”
He agreed that preppie styles have always been foundational in menswear “and then other things are layered on top. And for men, that’s a great place to exist — most can do that successfully and look good.”
A look from Brendon Babenzien’s inaugural men’s collection for J.Crew.
Courtesy of J. Crew
As a result, “preppy isn’t going away anytime soon,” he said. “It will always be there but we will see it evolve into other parts of American style, but tangentially.”
But as a fashion trend, “I think prep will be here for a while. With Jonathan Anderson, we should be good through at least next fall. For a lot of people, this is the first time they’re seeing this, so I think we’ve got another 24 months. I think we’ll see it for a couple of years on the trend side and then it’ll be foundational after that. It’s the start of a relatively long cycle.”
Jack Carlson, founder of Rowing Blazers and now president and creative director of J. Press, said: “The preppy look is perpetual, but the extent to which it influences the runway and penetrates other genres and markets changes over time — and by those measures, it is in ascendance. I think this has been percolating for years, but it’s really hit its stride in 2025.”
He said preppy is “a nebulous word, and there are many different denominations within it. I think in 2006 to 2013 or so, we saw a maximalist, English-inspired version blossom, led by labels like Rugby. That was the era of Jack Wills, Gant Rugger, J. Press York Street, Brooks Brothers Black Fleece and Red Fleece. A now-famous 2009 photo of Kanye [West], Virgil [Abloh] and their crew at Paris Fashion Week shows both how colorful and maximalist this look could be, and the extent to which it penetrated culture more broadly.”
But by the early to mid-2010s, “I think a much more pared-down shade of preppy came to dominate the ‘Millennial optimism era,’ epitomized perhaps by the J.Crew Ludlow suit. And more recently, I think a more ‘90s-inspired variant came to the fore, taking some cues from streetwear and from 1990s Ralph Lauren: Aimé Leon Dore, Rowing Blazers and Noah were all part of this.”
Jack Carlson’s J. Press spring 2026 collection.
Courtesy of J. Press
But to Carlson, there’s a new chapter in 2025: Ivy style. “The predecessor of preppy, as well as a subgenre within preppy, is enjoying a resurgence,” he said. “I see it on the runway, social media, celebrities, tastemakers, etc. The ‘old money aesthetic’ microtrend helped to influence it perhaps, but this is a much bigger movement.”
At J. Press, the company that he said essentially created Ivy style, “we can’t keep our Made in USA tweed sport coats in stock. Same with our Made in Scotland Shaggy Dog sweaters, and really classic Ivy outerwear pieces like our Made in USA camelhair polo coat. I think this is the beginning of this movement, and I think it will last a long time. The last major cycle for preppy was that 2006 to 2013 period. That was a good eight years. But the good news for brands like J. Press is that this look never goes away. And while trend-driven fashion labels can play on this aesthetic more or less in any given season, J. Press is always going to be its authentic home.”
