Sperry Boat Shoes Won Me Back. I Never Should've Docked 'Em
ShoppingThe OG Top-Sider is in high demand again, but the 90-year-old brand makes so much more than maritime mocs.By Leon HedgepethMay 23, 2025Photos courtesy of Leon Hedgepeth; Design courtesy of Emily HanhanSave this storySaveSave this storySaveAll products featured on GQ are independently selected by our editors. However, we may receive compensation from retailers and/or from purchases of products through these links.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 HedgepethFast-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).SperryGold Cup Authentic Original 2-Eye Woven Boat Shoe$195 SperrySperryAuthentic Original Made in Maine 2 Eye Boat Shoe$375 SperryThe 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.Leon HedgepethThe canvas CVO sneaker (a Paul Newman favorite) still uses a traditional vulcanization process that locks the upper to the outsole; the Sperry Authentic Original boat shoe still has hand-sewn moc construction, Blake stitching linking the uppers to the sole, and the same Razor-Cut Wave-Siping developed by founder Paul Sperry in 1935 to hug a slippery ship deck like it’s your aunt at a family reunion. For the real Made in the USA connoisseurs, Frankel points to Sperry’s Made in Maine line as the crown jewel: limited in number and handcrafted at the family-owned Rancourt factory in Lewiston, Maine from top-tier US-sourced leather.SperryRacquet Oxford$90 $35 Sperry$90 AmazonSperryClassic CVO Sneaker$70 Sperry$60 AmazonAfter the Racquet Oxford sneakers became daily drivers, I was ready to set sail again. I picked up a pair of Authentic Originals from Sperry’s Gold Cup collection, a premium line launched in the mid-'90s with upscale details and materials like woven suede. I also got the right size this time. They felt great out of the box, and they get better with every wear—by design, I learned.Each pair is lined in lambskin, which molds to the shape of your foot over time, so the best days are ahead. (It also handles sweat and moisture better than cowhide.) A layer of memory foam over EVA gives more comfort than you’d expect from a fairly thin sole.I started my Sperry journey as a young man with suspect spatial awareness, but now? I’ve got a dozen pairs from the brand in rotation, including duck boots, woven penny loafers that rarely leave my feet once June hits, and a pair of heavy-duty Vibram boat shoes that look like they could survive a hurricane.“In a culture that moves fast, there’s something refreshing about putting on a pair of shoes that don’t chase trends, but still look completely at home in the moment,” said Frankel. I like to think that, same as Sperry’s boat shoes, my style’s getting more lived in and legit with age. At the very least, I’m still not wearing any of the shoes with Nike Elites.SperryCold Bay 3-Eye Thinsulate Duck Boot$110 $70 Sperry$110 $88 AmazonSperryAuthentic Original 3-Eye Vibram Boat Shoe$200 $100 Sperry
All products featured on GQ are independently selected by our editors. However, we may receive compensation from retailers and/or from purchases of products through these links.
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.
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.
The canvas CVO sneaker (a Paul Newman favorite) still uses a traditional vulcanization process that locks the upper to the outsole; the Sperry Authentic Original boat shoe still has hand-sewn moc construction, Blake stitching linking the uppers to the sole, and the same Razor-Cut Wave-Siping developed by founder Paul Sperry in 1935 to hug a slippery ship deck like it’s your aunt at a family reunion. For the real Made in the USA connoisseurs, Frankel points to Sperry’s Made in Maine line as the crown jewel: limited in number and handcrafted at the family-owned Rancourt factory in Lewiston, Maine from top-tier US-sourced leather.
After the Racquet Oxford sneakers became daily drivers, I was ready to set sail again. I picked up a pair of Authentic Originals from Sperry’s Gold Cup collection, a premium line launched in the mid-'90s with upscale details and materials like woven suede. I also got the right size this time. They felt great out of the box, and they get better with every wear—by design, I learned.
Each pair is lined in lambskin, which molds to the shape of your foot over time, so the best days are ahead. (It also handles sweat and moisture better than cowhide.) A layer of memory foam over EVA gives more comfort than you’d expect from a fairly thin sole.
I started my Sperry journey as a young man with suspect spatial awareness, but now? I’ve got a dozen pairs from the brand in rotation, including duck boots, woven penny loafers that rarely leave my feet once June hits, and a pair of heavy-duty Vibram boat shoes that look like they could survive a hurricane.
“In a culture that moves fast, there’s something refreshing about putting on a pair of shoes that don’t chase trends, but still look completely at home in the moment,” said Frankel. I like to think that, same as Sperry’s boat shoes, my style’s getting more lived in and legit with age. At the very least, I’m still not wearing any of the shoes with Nike Elites.
