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.’”

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