Sperry and Pleasures have reunited for their second collaboration.
For the duo’s latest tie-up, the Los Angeles-based streetwear label has updated three Sperry footwear styles that draw on Pleasures co-founder Alex James’ roots in New York and New Jersey’s alternative music scenes as well as a “shared appreciation” for the boat shoe.
“This collaboration has always been about reimagining something timeless through a subcultural lens,” James said in a statement. “Sperry has such a rich heritage, while Pleasures brings bold, raw energy. Together, we’ve created something that’s both nostalgic and radically new.”
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First up in the offering is the 3-Eye Vibram Reflective Cold-Bay, which pairs a reflective leather and rubber upper with Thinsulate insulation and a leather insole. The style also includes a Vibram 262K New Bifida outsole, reflective hiker laces, and a secondary lace option.
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Up next is the 3-Eye Vibram Turn-Lock Lug Boat, which reimagines the classic boat shoe with a lace-free turn-lock dial closure and a Vibram 884C Bristol Lake outsole.
Finally, the 3-Eye Vibram Hiker features a soft calf leather lining and insole and a Vibram 629C Vybrid Hike outsole.
To highlight the collection, the duo captured the styles amid the vineyards and rolling, oak filled hills of Avenales Ranch in California.
“This collaboration has always been about reimagining something timeless through a subcultural lens,” James said in a statement. “Sperry has such a rich heritage, while Pleasures brings bold, raw energy. Together, we’ve created something that’s both nostalgic and radically new.”
Jonathan Frankel, president of Sperry, added that the partnership with Pleasures “continues to challenge” what the footwear brand can represent.
“By merging our rich heritage with Pleasures’ boundary-pushing vision, we’re redefining classic silhouettes for a new generation that values both authenticity and creative expression,” Frankel noted.
The Sperry x Pleasures collection, which retails between $150 and $225, will be released in U.S. men’s sizes 7–13 on Nov. 18 at Pleasuresnow.com and Nov. 19 at Sperry.com.
Sperry and Pleasures first linked up in 2023 to update the footwear brand’s Authentic Original 3-Eye boat shoe into a creeper style. The other silhouettes in the range include the Captain’s Oxford delivered with distressed pewter leather, a fur-lined Moc-Sider Mule with pronounced Pleasures branding at the top and two colorways — black and cream — of the Float Slide with punk fishnet print.