The boat shoe trend has come ashore. It started 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 polo 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.
The Miu Miu interpretation of the boat shoe was different, of course, from the buttoned-up preppy stylings made famous by 20th-century icons like JFK or Princess Diana. This was a boat shoe uninhibited: loose, messy, and undone in a way that felt real and relatable.
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 polished feeling that has now become irresistible to the fashion set—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 by Paul Sperry, designed its signature shoe with non-slip soles for enhanced sturdiness when worn on actual boat decks.
The shoes first gained popularity beyond actual sailors during the ’60s and ’70s when they started to be worn by the likes of JFK and Paul Newman. They were further crystallized as the footwear of choice among American prepsters with the 1980 release of the Official Preppy Handbook. “Boat shoes have stood the test of time by striking the perfect balance between classic style, and timeless craftsmanship,” says Jonathan Frankel, president of Sperry. “Rooted in 90 years of heritage, yet constantly evolving, this iconic style stays fresh through modern updates, collaborations, and endless opportunities for customization.”
Sperry’s most recent collaboration, with Aritzia, consists of two riffs on the boat shoe, offering a slim-cut version and an Original Sperry version, all equipped with customizable colorful laces.
While the collection initially sold out within a few hours, it’s back in stock on Aritzia, but chances are—these won’t last, so act quickly.
Marissa Galante Frank, fashion director at Bloomingdale’s, is seeing the style resonate with customers in a big way. “They are beloved by both the fashion customer who saw them on the runway and the classic customer who never abandoned the silhouette.”
Now that boat shoes are back, it’s all about incorporating them into your everyday style. “I love the boat shoe as a more casual and comfortable option to the loafer,” says Enamorado. “My favorite 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 colorful socks.”
I love styling my Miu Miu boat shoes for daily office looks, with sleek tailored trousers or pleated A-line skirts. They add a sense of ease to my office looks; a not-too-polished polish.
Ahead, shop the best boat shoes on the market, from tried-and-true classics to fashionable iterations.