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Style Advice

Style SOS: How do I pull off boat shoes?

Style SOS: How do I pull off boat shoes?

"I love how easy and comfortable boat shoes are, but I'm not a preppy dresser usually. Can I still pull them off?" - Jacob via email

While boat shoes are generally linked with more preppy styles of dressing, you definitely don’t have to dress like an Ivy Leaguer to wear them. As the name suggests, boat shoes were originally designed to stop sailors and boaters from slipping on wet decks. From these functional beginnings, they were adopted as a fashion statement by yacht owners, which is why we often think of them as a preppy style. But the soft leather and sole, the low tongue, and the short laces make them great for warmer weather when you don’t want to wear sandals, but don’t need formal footwear either.

“Because of their inherently preppy look, boat shoes work best with classic styles like polos and chinos,” says stylist Artemis Crowley. “You can style them into a more contemporary look by choosing a tipped collar or knitted polo and a pair of cropped loose or tapered chinos. Simple styles will help you to avoid the preppy vibe, so be sure to keep things fairly minimal and wear no-show socks to keep your shoes in good condition.” 

Boat shoes are an easy way to show that you’ve made a little bit of effort, as they still look considered when paired with the most laid back warm-weather outfits. Just don’t take them too far out of their comfort zone, and steer clear of boat shoes with formalwear.

If your style is more indie-inspired, take inspiration from the  likes of Vampire Weekend and other influential bands, who adopted boat shoes in the mid-00s. They prove that the style also has a place in alternative summer wardrobes. Think rolled-up jeans, a denim shirt worn open over a grey t-shirt, and a blazer if you need extra layers. The look nods to preppy roots, but each piece alone is versatile and not tied to any specific style. So go ahead and style them in the way that feels right for you – no polo shirt (or yacht) required. 


Words: Ella White
Illustration: Ryan Gillett