Sometimes fashion just seems like “Groundhog Day” with better outfits. Designers vanish only to reappear suddenly (looking at you, Alessandro Michele.) Trends sputter out and abruptly are back. Skinny jeans were cool until everyone was wearing oversize drop-crotch khakis — everyone, that is, except that cadre of teen style-setters intent on bringing back 2000s-era jeggings so bad they’re good.
Consider, in this vein, the boat shoe, echt signifier of all things preppy. All but defunct as an element of a stylish wardrobe, it has now become a hot item. This is “the year of the boat shoe,’’ says Vogue, which is far from alone in observing a proliferation of fashionable maritime footwear.
There they were on the Miu Miu spring 2024 runway in Paris, in what was widely considered one of Miuccia Prada’s best collections for that label in years. There, too, they were at Fendi’s fall 2024 men’s wear show in Milan, where the moccasin-style shoe had been stamped to look like crocodile. There they are on virtually every page of a new catalog from the revived hipster heritage brand Quaker Marine Supply Co., a label whose style paragon is not Jacob Elordi but “Papa” Hemingway.
“Every few years there’s another wave,” Lisa Birnbach, 65, the author of “The Official Preppy Handbook” and its sequel “True Prep,” said of boat shoes like Sperry Top-Siders or the similarly beloved, if nautically inappropriate, L.L. Bean Camp Moccasins (they scuff decks).
Ms. Birnbach’s “Handbook,” originally published in 1980 as a satirical take on upper-class folkways, went on to become a canonical text, right up there with “Take Ivy,” a slender volume of photographs from 1965 depicting long-ago Ivy League guys. Both are inevitably cited whenever preppy trends cycle through again. And each time that happens, Ms. Birnbach knows her phone will ring. “My telephone number must be on the bathroom wall at Condé Nast and Hearst,” she said on a call from her home in Glendale, Calif.
The renewed interest in boat shoes could be inspired, Ms. Birnbach said, “by a new retailer selling Top-Siders, a designer that discovers them, an Instagram or TikTok person that puts themselves together with boat shoes in a clever way.” Regardless, she said, it always seems as if people are seeing them for the first time, which is odd for a category of footwear created when Franklin D. Roosevelt was president.
It was in 1935 that Paul Sperry, the inventor of Sperry Top-Siders, is said to have slipped on the deck of his sailboat and fallen overboard into the Long Island Sound. He later experienced a soggy epiphany, out of which came a shoe for boating with simple leather uppers and incised rubber soles that mimicked the ridges on his cocker spaniel’s paws. (Mr. Sperry patented the process of making those grooves, termed “siping,” in 1937.)
The Top-Sider is “the Platonic ideal of the shoe,” said Jason Jules, the author of “Black Ivy,” a 2021 book examining how generations of Black men adopted, improvised upon and made their own the elements of a sartorial code that originated among a largely white Ivy League elite.
“The sudden re-emergence of the boat shoe in fashion is partly a reaction to sneaker fatigue,” Mr. Jules, 60, said on a call from his home in Paraguay. “With sneakers, you’re so overwhelmed by details that you need a manual to know how to wear them.”
Conversely, as any yachtie can testify, Top-Siders are so elementary in their design they barely qualify as a shoe. And though the style has been reinterpreted in pop colorways, metallics and subject to cool designer affiliations (most notably a fashion-bro-friendly collaboration with Chris Echevarria of Blackstock & Weber), it is the classic version that continues to resonate.
“It’s the style iconography,” said Jonathan Frankel, the president of the Aldo Group, whose portfolio includes Sperry. “It ain’t broke, so don’t fix it.’”
On a recent phone call from his company’s headquarters in Florence, Ala., the designer Billy Reid, 59, noted that he’d bought his first pair of Top-Siders at 15 and then “wore them until they were held together with duct tape and Shoe Goo.” Now, he said, seeing 20-somethings wearing Top-Siders “blows my mind.”
Though Mr. Reid replaced his boat shoes with some regularity through the years, eventually he consigned them to the back of his closet. And there they remained until “my 20-year-old son, Walton, started stealing them.”
Therein lies the paradox of the boat shoe, according to Kevin McLaughlin, the owner of Quaker Marine. Styles like Top-Siders are rooted in function, not fashion. Yet they are “simultaneously always coming into fashion again,” he said.
For Walton Reid, Mr. Reid’s 20-year-old son and a musician, the anti-fashion vibe of a boat shoe is intrinsic to its appeal.
“The way style works now, you can take inspiration from a utilitarian classic and put whatever spin on it you want,” he said. “I can walk into a thrift store, find a pair of Dior jeans somebody may have died in, wear them with a suit jacket and boat shoes and, even though it shouldn’t work, it does.”