Boat shoes are finally getting their day in the sun. Spurred on by the resurgence of prep and Americana more broadly—think Zendaya serving tenniscore in Challengers, TikTok co-opting the old money aesthetic, and Bella Hadid's equestrian era—the boat shoe trend revival has been percolating for a few seasons now, with early co-signs from Miu Miu and JW Anderson. But I wasn't convinced until I started seeing Sperry top-siders bounce down the spring Spring 2025 runways and worm their way into the wardrobes of fashionable women like Nordstrom associate fashion director Linda Cui Zhang, who recently took her tricked-out brown leather Sperrys to New York Fashion Week.
"I customized them with some beads from Don’t Let Disco and it makes them that much more special, and personalized," she tells me. "They offer a more relaxed look than a classic loafer."
Elsewhere at New York Fashion Week (NYFW), street style muses have been pairing their boat shoes with slip skirts, baggy trousers, hot pants, and knee-socks. Collina Strada's Hillary Taymour sent mud-caked black leather Sperry boat shoes down her outdoor catwalk. Ella Emhoff was photographed wearing the same style sans mud in the front row.
The boat shoe trend got another nod at NYFW from Monse, where models hit the catwalk in slouchy black socks and three different Sperry styles: the Authentic Original Boat Shoe, the lug-soled Wells Boat Shoe, and the extra-chunky Bayside Boat Shoe. The show, which opened with a jacket Michelle Obama recently wore at the Democratic National Convention, was a landscape portrait of American sportswear influences. By pairing the boat shoe with prairie-ready dresses and city-chic blazers, designers Laura Kim and Fernando Garcia demonstrated how a shoe style meant for sea-faring can be re-contextualized for land-dwelling.
Allie Pellerano-Rendón, co-founder and CEO of the fashion consulting agency Collection Atelier, has been wearing boat shoes—from black glitter top-siders to brown ballet flat-inspired versions—all her life. She tells me she's originally from Connecticut, where boat shoes reached uniform status decades ago.
"Although my closet is no longer lined with them, I do have two pairs left that I still wear," she says. "To me, the boat shoe carries the same energy as the L.L. Bean boot. It’s classic, nautical, Americana, East Coast energy."
With Fashion Month falling right between the summer Olympics and the upcoming election, it just feels right to see nostalgic American styles re-enter our collective consciousness. But there may be another reason the boat shoe is seeing such a concerted push this season, Pellerano-Rendón says.
"Collaborations are the key to cool in the fashion world right now. Since the licensing for Sperry was taken over by the Aldo group this past year, that is exactly what Sperry has been focusing on," she says, citing the brand's summer collaborations with Tod Snyder and Palmes Tennis Society. "The energy and the audience of the boat shoe is definitely shifting with these collabs."
We've seen what can happen when designers decide to elevate an overlooked shoe. The Ugg boot comeback tour and the neverending Crocs craze offer a glimpse of just how far the humble boat shoe trend could go with a little wind in its sails. Here's hoping Sperry teams up with Dries Van Noten next. But if you're looking for a something a little freakier than a traditional boat shoe, look no further than Labucq's It Girl-ified verison, which comes outfitted with metal beads.
