We Can’t Believe These “Ugly” Shoes Are Back—4 Styling Ideas That Are Actually So Chic

When we think about fall’s preppy fashion trend, many clothing and footwear options spring to mind. Amid this array of styles, a notable resurgence is capturing attention—the revival of boat shoes for women.

Initially crafted as sturdy and practical footwear tailored for sailing, boat shoes have transcended their utilitarian origins to become a timeless fashion essential. They first made waves in the late 2000s, but their allure has returned, garnering favor among devout followers of fashion trends.

Today’s boat shoes resemble those worn in 2012; however, the styling has been refreshed. After analyzing numerous boat-shoe outfits, it’s evident that there’s a chic way to wear them—style boat shoes the same way you would loafers. For example, fashion aficionados in Paris pair their boat shoes with loose-fitting and light-colored denim, a simple T-shirt, a casually cool leather jacket, and a rich-looking suede bag. Those in Copenhagen pair them with boxer shorts, ankle socks, and a cardigan. London fashion people are also wearing them with monochromatic suits, and fashion enthusiasts in New York are accessorizing the shoes with straight-leg sweatpants, a baseball cap, and a trench coat.

Similarly to loafers, we’re seeing classic leather iterations dominate. Still, fashion people are welcoming a few fresh boat-shoe styles, like chunky platforms and low-profile suede ones, onto the scene. If you need one more reason to justify your purchase, know that we just saw boat shoes on the spring 2025 runway at Monse, indicating that this style isn’t going out of fashion anytime soon.

With that said, look below at the four winning boat-shoe outfit formulas that the style set is behind.

Nothing complements brown leather boat shoes and ankle socks like a versatile, trusty denim dress. Add a matching bomber jacket or chunky sweater over your shoulders for the perfect fall daytime look.

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This outfit perfectly exemplifies the wrong-shoe theory, where boat shoes are mismatched with a sophisticated blazer and pants. The boat shoes work well in this context by transcending their original sporty and preppy function and appearing as a deliberate and refined choice.

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This fall ensemble is one of our favorites. It features a distressed brown leather jacket, a striped button-down shirt, and classic jeans. While any shoes would have worked, the boat shoes added a modern touch to this otherwise classic look.

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Elsa Hosk’s choice of red boat shoes showcases a refreshing update to this classic style. To style them, she skillfully incorporates one of the season’s most prominent dress trends, a drop-waist dress, demonstrating a keen sense of modern fashion. To further enhance the versatility of her look, she complements it with socks. It’s an ideal transitional outfit suitable for the shift from summer to fall.

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