The boat shoe trend is nostalgic, cheeky, and so easy to wear

Whether you’re on board or not, the boat shoe trend has come ashore. We first spotted boat shoes taking a fashionable turn on the runway at Miu Miu’s Spring/Summer 2024 show. There, a model came down the catwalk wearing a matching dark brown leather jacket and skirt set, layered over a preppy-style collared shirt that peeked out of her v-neck sweater. “It took an Italian brand like Miu Miu to make us want to dust off our Preppy Handbooks, embrace this collegiate trend, and start dressing like a ‘80s John Hughes movie,” says Harper’s Bazaar’s accessories director, Miguel Enamorado, about the boat shoe redux.

However, the fashion at Miu Miu was different from the buttoned-up preppy fashion made famous by 20th century icons like JFK or Princess Diana. It exhibited a loose, messy, and undone characteristic that felt real, relatable, and effortlessly stylish. Similarly, during Bally’s Spring/Summer 2024 show, a model sporting a pair of black leather boat shoes was dressed in a sleek black leather blazer and mini short set paired with a pale blue button-down shirt. The boat shoes styled in this city context evoked a downtown edge that has now become irresistible to the fashion set—spotted on street style and a favourite among editors, Enamorado and myself included.

While Miu Miu and Bally offered their own fashionable takes on boat shoes, we’d be remiss not to mention the original boat shoe maker—Sperry. The brand, founded in 1935, is known for designing the first boat shoe with a non-slip sole, which was, perhaps unsurprisingly, created to be worn on actual boat decks. The shoes first gained notoriety beyond actual sailors during the ‘60s, ‘70s, and ‘80s when they became popular among the likes of JFK and Paul Newman. They were further crystallised as the footwear of choice among American prepsters with the 1980 release of the Official Preppy Handbook.

Now that boat shoes are back, it’s all about styling them in accordance with your personal style. “I love the boat shoe as a more casual and comfortable option to the loafer,” says Enamorado. “My favourite is the Bally Plume. It’s handmade in Switzerland, so it brings a very upscale construction and leather component to this very casual shoe style—one that can be dressed up or dressed down, especially with colourful socks.”