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How two New England brands are reclaiming authentic preppy style, one tennis polo and collar roll at a time.
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The Boast “1983” pique polo and performance shorts. Clay court not included. (Also, that’s a Japanese maple leaf, ahem.) / Photo by Nina Gallant / Styling by Taylor Greeley for Artists with Agency
Bright colors, big bows, cheeky graphic tees: We’ve all seen the Gen Zers sporting ironic, hyper-stylized “preppy” looks on social media. While cute, the trend has always felt far removed from the original meaning of American prep: heritage clothing built to last. Now, it looks like the pendulum is swinging in the other direction, thanks to two New England brands that are reinvigorating the old-school preppy aesthetic for a new generation.
In 2024, the dormant tennis brand Boast—known for replacing stiff country-club whites with polos and warmup suits designed by players, for players—was purchased by footwear exec Matthew Feuer, setting the stage for a thoughtful return to form under a Boston-based leadership team. And unlike the trend-driven version of preppy dominating TikTok, Boast’s looks have and always will be rooted in sport. “Our version of ‘preppy’ comes from the court, the clubhouse, and the rituals around the sport,” says chief brand officer Sunni Fleming, who helms the Boston-based leadership team. “It’s always been about performance, personality, and knowing the rules well enough to break them.” In other words, tennis isn’t a styling reference for this company—it’s the foundation. The concept is clearly a winner: The brand returned to the tennis world with a presence at the U.S. Open and the debut of its new women’s line last fall.
Boast’s high-waisted pleated skirt. / Courtesy photo
That return to authenticity is echoed on the formal side of prep at J. Press, the more than 120-year-old standard-bearer of Ivy League style, which made an unexpected runway debut this past September at New York Fashion Week, with a follow-up show in February. Last year, the brand hired Boston-bred Jack Carlson—a former national rowing coxswain whose fashion brand, Rowing Blazers, was sold to Burch Creative Capital in 2024—as creative director, tasking him not with reinvention, but with restoration. “Most brands, over time, stray in bigger or smaller ways from the things that made them really special in the first place,” says Carlson, noting that some of J. Press’s Ivy League design hallmarks had fallen by the wayside in recent years. Part of Carlson’s role has involved recommitting to these classic details—patch pockets, old-school collar rolls on Oxford-cloth button-downs—and reinforcing the brand’s authority as the foundation of American prep.
The brand’s Argyll & Sutherland cable-knit cricket sweater. / Styling by Taylor Greeley for Artists
After all, authenticity, Carlson argues, is what separates classic prep from trend-driven interpretations. “It’s not something that goes in and out of fashion,” he says. “J. Press is timeless.” That philosophy extends to production: J. Press manufactures much of its clothing in the United States, including a significant amount in Massachusetts, and is actively searching for a store location here—ideally in Harvard Square, where its Cambridge outpost stood for more than 80 years. If classic prep is going to reassert itself anywhere, Harvard Square—home to one of the country’s original Ivy League campuses—is the most obvious place to start.
Embroidered corduroy pants. / Courtesy photo
J. Press ties in classic and whimsical patterns. / Photo by Nina Gallant
This article was first published in the print edition of the March 2026 issue with the headline: “Prep Rally.”
