"When someone asks me how old I am, I say “old enough to remember wearing Sperry’s Top-Siders to school every day.” Although I took my allegiance to boat shoes very seriously back then, it couldn’t have prepared me for what was to come this spring. After years of laying dormant, the preppy shoes—which originally found their footing (literally) as the classic New Englander’s everyday footwear staple in the early ‘60s—have once again risen to popularity.
We first saw boat shoes trickle back onto the scene last spring, when designers at Prada, Miu Miu, and Bally set the internet ablaze by having reinvented top-siders walk down runways. Unlike years past, they weren’t worn in the totally preppy way you might expect; instead, their versatility was shown by being styled with more contrasted pieces, like high-shine leather and polished, top-handle bags. It allowed the once preppy-exclusive piece to be thought of as more than just an accessory for East Coasters or frat boys—now, you can style them with just about anything.
In case you’re not exactly on board (get it?) just yet, keep scrolling for our favorite ways to style the boat shoe revival and the best boat shoes to shop in 2025.
How to Style Boat Shoes in 2025
1. With a barn jacket and rugby shirt
The fashion crowd’s most-worn formula for styling a pair of boat shoes is with a striped rugby polo and a utility jacket (or more specifically, a barn jacket). The pairing is the perfect blend of land and sea, tying back to the traditional fisherman aesthetic, but in a city-inspired type of way.
2. With a trench coat and slouchy bag
If your style veers more classic, pairing your boat shoes with a trench coat is always a good idea. To keep it interesting, though, swap your go-to crossbody bag for a slouchy shoulder bag or tote.
3. With a chunky sweater and long shorts
This look is proof that boat shoes are easier to style than one might think. Pair them with long denim shorts—or baggy jeans, depending on the weather—and an oversized sweater for an easy, all-day look that’s both cool and comfortable.
4. With a structured jacket and white jeans
To avoid looking too nautical, swap slim-fit white jeans for baggy ones and layer on a suede jacket to complete the look.
5. With a leather jacket and straight-leg jeans
For an ultra-cool look, style boat shoes with an oversized leather jacket and slim-fit jeans. The contrast between the edgy jacket and classic shoe (and the relaxed top and fitted bottoms) will create an effortlessly chic effect.
Tinsley Crisp, Fashion & Beauty Staff Writer
Tinsley Crisp is a Fashion & Beauty Staff Writer at The Everygirl and specializes in reporting on the season’s latest trends and hottest products. As a New York City-based stylist, she’s committed to injecting joy into the art of getting dressed and delivering attainable yet aspirational content to our readers.