It is finally happening: those shoes that your posh friend’s dad wore to slope to the shops are being spotted on trains, buses and pavements everywhere. Their return has been rumoured in industry circles for some time – Vogue even dubbed 2024 the year of the boat shoe in February – but no one was quite sure if it would materialise in the real world, outside Nantucket. But lo and behold, there they are, on the feet of people who don’t know their port from their starboard, miles from any boats.
The resurgence of the design can be traced back to the catwalk. Miu Miu, the label designed by Miuccia Prada, featured multiple boat shoes in its spring/summer show. Its versions are for sale for £660 but the label is so influential that resale app Depop credit it for a rise in the popularity of boat shoes. Searches were up 39% last month, with Timberland and Sebago popular brands, available from £12 to £90.
Other designer brands are in on the trend, too. Loewe featured some bulbous boat shoes for autumn/winter and in Aimé Leon Dore’s most recent advertising campaign, Arsenal player Declan Rice wears boat shoes with white socks.
A spokesperson for Depop says they are part of a wider trend. “Rumblings of a preppy style revival have been on the cards for some time … the trend cycle appears to be shifting to classic and more conservative looks.” References range from the original Gossip Girl series and JFK in Hyannis to American influencer Emma Chamberlain.
Boat shoes have long been associated with the preppy look in the US – worn with polo shirts and chinos by the yacht-owning elite in the Hamptons. In the 1980 bestseller The Official Preppy Handbook, Lisa Birnbach wrote that membership of the preppy elite will be judged on footwear: “The Right Shoes give you a fighting chance.” The Sperry Top-Sider, a classic boat shoe, fitted the bill.
In the UK, they were part of the uniform for the equally well-heeled Sloane Ranger in the 1980s. Peter York, the co-author of The Official Sloane Ranger handbook, sees them as shoes “for blokes who like to mess around in boats”. He says wearing them was part of a wider way to signal the trappings of the upper class. “You lived in Parsons Green… [but] you wore Barbours [to say], ‘I’m certainly not part of this urban life.’ That works for boat shoes, too.”
The design dates back almost 100 years. Legend has it that sailor Paul Sperry slipped on the deck of his boat and fell overboard. He later noticed his dog could walk on ice without slipping thanks to the texture on its paws, and cut slits into the bottom of his rubber shoes, meaning more grip on a wet surface. He launched the Sperry Top-Sider in 1935. Other brands followed, including Sebago, GH Bass and Timberland, and the designs became a favoured footwear of those with enough disposable income to own a boat.
Of course, most people wearing boat shoes in 2024 are not part of this demographic. Jason Jules, author of Black Ivy, a book exploring the preppy-adjacent Ivy Look as worn by Black Americans in the 1950s and 60s, says the current interest in them fits into the “old money aesthetic” that is popular on TikTok and that leans to the classic and discreet designs long favoured by the wealthy.
However, Jules – who himself has a large collection of boat shoes – sees the focus on this design classic not simply as an attempt at “looking rich” but rather as a reaction to fast fashion. “People are being a lot smarter with their money,” he says. “A not-heavily-branded pair of shoes lasts you 20 years without much reinvestment or change. [It] is a cost-effective way of dressing.”
With trainers dominating fashionable footwear for most of the last decade, boat shoes also make a change from the endless variety of sports-based footwear. “If I say to you ‘a sneaker’, you have got a whole world to analyse – from a Vans canvas shoe to a Nike Air Jordan,” says Jules. “A boat shoe is always going to be, affectionately, a boat shoe.”
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