Are boat shoes the new loafers? A menswear expert investigates

Loafers had their time in the sun, endorsed by the likes of Jacob Elordi, Harry Styles, et al. But the boat shoe resurgence? That’s snuck up on me. I’ll be honest. I used to really not like boat shoes. In fact, one of the earliest pieces of dating advice I remember receiving was the classic adage: “you can tell a lot about a man by his shoes”. However, I think in the bright, purging glow of 2026, I’m about to eat my words.Prep and collegiate styles have staged a major comeback in recent years. Rugby shirts, knit polos, leather shoes, tube socks, baseball caps and ringer tees have marched down runways and punctuated street-style mood boards just about everywhere. So, it stands to reason that boat shoes should be back on the menu. As for what makes a boat shoe a ‘boat shoe’, let me break it down. This won’t surprise you, but boat shoes were specifically designed to be worn on the wooden decks of boats. The boat shoe origin story goes back to 1935, when Paul Sperry slipped on a wet deck, fell overboard and felt he needed more robust footwear for his sailing trips. Fast forward ninety-one years, and his grooved-sole shoe has left the high seas and found its place in city wardrobes, where it will see a lot more of East London’s pavements than yacht decks. Timberland® Authentic 3-Eye Lug Handsewn Boat Shoe for Men in BrownTimberlandHailing from Timberland’s back-to-school campaign, these boat shoes are defined by their chunky rubber sole and contrast stitch detailing. They’ll look their best with wide-leg or barrel-leg trousers, FYI.Barbour Deck tartan leather boat shoeAsos DesignI’m drawn to these Barbour boat shoes for one simple reason: that tartan panel. A Barbour signature, this detail lends a quintessentially British feel to the Ivy League shoe. Grenson Claude boat shoesGrensonLess edgy and more elegant, Grenson’s boat shoes are characteristically sleek, tailored and luxe-feeling. Cutting a more low-slung, slim silhouette, Grenson’s Claude shoes are more akin to a loafer than any on this list, making them a good sartorial stepping stone for those more in the loafer game right now.