Sperry Boat Shoes Won Me Back. I Never Should’ve Docked ‘Em

Like you, I’ve watched trends rise, die, and rise again like Last of Us zombies, but with more pleats. Which had me thinking about the recently revived boat shoe—specifically, Sperry boat shoes, my gateway drug to a brand that’s now taking over my shoe collection.

I remember getting my first pair of Sperry Top-Siders, the (literal) OG boat shoe, back in high school. I bought them from a Sperry outlet as one of my first grown-up shoe purchases, and teamed them up with a pair of jeans my mom scored using Kohl’s Cash and a plaid button-down from Gabriel Brothers. It was a rough look, but at least I wasn’t pairing my Sperry boat shoes with bone-white Nike Elite socks, swagless frat bro style, in case a surprise game of 21 broke out. My Top-Sider love faded quickly, mostly because mine were a size too big, grating my heels with every step. They shortly landed in the back of my closet.

Leon Hedgepeth

Fast-forward a decade or so, and I gave the brand another shot—not with the classic Top-Siders, but the brand’s retro-reissue Racquet Oxford sneakers. That’s about when Sperry started quietly playing the collaboration game, and doing it really well: team-ups with Blackstock & Weber founder Chris Echevarria, Beams Plus, Todd Snyder, and (up soon) Colbo. None of those shoes shot off on a hype rocketship, but that wasn’t the point. According to Sperry President Jonathan Frankel, it wasn’t about a comeback. “We’ve always been a pillar in the canon of American style and always will be,” he told me (well, bragged to me).

The purpose of it all those team-ups is to reintroduce the 90-year-old brand to a new generation. “Sperry’s resurgence isn’t about chasing trends—it’s about recontextualizing our icons: the Authentic Original Boat Shoe, the Classic CVO, and the Captain’s Oxford,” Frankel said. For Sperry, inventor of the boat shoe, the heritage is the story. The principles that made the brand iconic—inventiveness, functionality, simplicity, craft, and a quiet confidence—just needed a fresh spotlight.