Are Boat Shoes Really Back?

Shannon Adducci
·7 min read

Photographs: Getty Images, Dries Van Noten; COllage: Gabe Conte

Another summer, another round of boat shoe discourse. It feels like just about every year—or at least every time a new Vampire Weekend album drops—there’s a fresh debate over whether the oft-derided, dad-coded slip-ons are “back.” This latest boat shoe media blitz, however, feels especially notable. They’ve been creeping their way back into fashion-world consciousness in recent seasons via the runways of Miu Miu and JW Anderson, making headway among “old money style”-obsessed Gen Zs on TikTok, and attracting headlines across the internet.

The question is: Are boat shoes actually back now, just because designers and newspapers are telling us they are? The veteran designer Todd Snyder, for one, says yes. “In menswear you have these pieces that are classics, they’re icons. Whether you consider it cool or not, once you hit classic, you’re forever in,” says Snyder, who recently dropped a collaboration with Sperry inspired by the white boat shoes he used to wear in the ’80s. “The boat shoe is forever in.”

Snyder’s not wrong in his assertion: For many, the boat shoe never went away. But the confluence of the 20-year trend cycle with the current old money obsession hints at an extra layer in the preppy shoe’s current return—something rooted in nostalgia, cultural cosplay, and a heavy dose of irony. The boat shoe is just one cog in the wheel of a revival machine that could bring back double popped polo collars or even a few Judge Smails-esque Ralphcore fits any minute now. “There’s always been a bit of that thing, looking in your dad’s closet and how you interpret it,” Snyder says. “But there’s definitely a vibe going on right now to be ironic in a way. I think that’s where it’s taking things that have a certain pedigree and figuring out how to reinterpret that in today’s tone, which is a lot more inclusive and less about status.”

Todd Snyder's '80s-inspired Sperry collaboration.
Todd Snyder's '80s-inspired Sperry collaboration.

While some conversation about the old money aesthetic has homed in on its history of gatekeeping non-WASPs—or the suggestion that a new, more diverse generation can subvert preppy style—that narrative might actually obscure parts of the boat shoe’s past. “As much as there might be a side of history where, this was a country club thing or this was something for white people, I look back at my history and I wore this stuff — my grandfather wore this stuff,” says Blackstock & Weber founder Chris Echevarria, who also heads up an American-made sub-label for Sperry.

Echevarria points to author Jason Jules’s 2021 book, Black Ivy: A Revolt in Style, for a closer look at how the likes of James Baldwin, Miles Davis, Sidney Poitier, and other 20th-century Black artists already claimed Ivy League fashion as their own decades ago. “The pictures that exist [in preppy culture] are prominently of white people because of where we were in history,” says Echevarria. “So there might not be as many pictures of black people wearing these things. But if you look at Martin Luther King, Jr., he wore Top-Siders. He has a presidential Rolex on in most of his photos. Most people would say that’s old money aesthetic.”

The designer classifies the boat shoe as an all-American classic, something everyone probably already has—and will need again someday. “You’re not going to wear Rick Owens to your grandmother’s funeral,” Echevarria says. “There is always a place for a Top-Sider. We don’t necessarily wear them all the time, but they are there. It’s part of the American wardrobe.”

The rise of low-profile shoes in menswear—from ballet flats to Mary Janes—also helped precipitate the boat shoe’s comeback. “The moment that shoes become the rug that ties the room together, as opposed to the main event, they kind of take a backseat in favor of something that promotes the overall harmony of an outfit,” says Jian DeLeon, Nordstrom men’s fashion director. “It’s about the nuance and contrast of stereotypically masculine big pants balanced out with something not as stereotypically masculine, like a low-profile shoe, including a boat shoe.”

Snyder agrees. “[Boat shoes are] your summer dress shoe,” he says. “It’s a nice way to dress up an outfit without being too serious.” He recommends pairing ‘em with a nice linen suit or light-wash jeans.

And while the luxed-up spins from labels like Dior and Fendi have garnered plenty of attention, DeLeon points to the Sperry Billfish as an option for those looking to pull off both function and fashion at a more advanced level. “The classic Top-Sider is the platonic ideal of the boat shoe, but the Billfish is what billionaires are actually wearing on their boats,” he says. “It’s something that has been embraced as an authentic style staple of a certain way of dressing. And because of that provenance, I think that’s the shoe that would be worn in an intentional fashion way. So many fashion trends now are around this idea of, ‘I’m going to pull this thing off.’”

Troye Sivan sporting boat shoes on the Miu Miu runway last fall.
Troye Sivan sporting boat shoes on the Miu Miu runway last fall.
Getty Images

For Jack McBride, a sailor who travels more than 2,000 miles annually in offshore trips around the Caribbean and up and down the Eastern Seaboard, a proper boat shoe shouldn’t be precious, meaning no leather or suede. “You have water splashing on the deck. If they get wet with salt water you can just hose them down and dry them out in the sun,” he says of the salt-washed twill sneakers he wears on his maritime excursions. McBride also touted the well-known rule that a boat shoe should only have white soles, to avoid any scuffing on white or teak decks. There’s also a difference between a boat shoe and a deck shoe: The former has a lacing system that runs around the entire perimeter to give a snug fit, while the latter might just slip on or use decorative laces.

Don Smith, a seasoned yachtsman whose Falcon 2000 raced with America’s Cup teams out of the New York Yacht Club, divides the world of boat shoes into three categories. “The first is the old-fashioned loafer type. It may have a good bottom but the shoe doesn't provide any support. The second is a strong athletic shoe with a squeaky bottom. It doesn’t slip and they advertise it as a shoe where water slips out from under it. It’s a racing shoe, like the Helly Hansen Skagen F-1 Offshore. The third has a lot of support, fabulous soles, and it’s something you would also wear to the bar. That’s what I have.”

And what does a real yachtsman think of wearing boat shoes and jeans? “Cool as a moose,” says Smith. “The idea is that I might not be a yachty but I identify with the glamor, the excitement, and the quest of yachting.”

Just don’t take those new suede Top-Siders of yours out to sea.

Originally Appeared on GQ

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