Everyone knows Sperry as the go-to for nautical footwear that stands the test of time. From loafers to boat shoes, the brand is an ultimate staple for elevated leisure shoes. While men are still looking for pieces that add a sophisticated touch to their wardrobes, it’s not enough to serve only one purpose. Far from having multiple options that serve various purposes, more users are looking for sleek pieces that can be dressed up or down. And while nautical-inspired footwear remains the hallmark of the summer season, it’s time that this timeless category receives a makeover that turns it into a year-round choice. Along with collaborator PLEASURES, Sperry unveils the second capsule collection with the Los Angeles-based brand, all about adding an edge to the prim-and-proper nautical shoe.
Sperry and PLEASURES ditch the sea for the street with a new collection

Introducing a new three-shoe capsule collection, Sperry and PLEASURES are channeling the charm of classic silhouettes and spinning them to fit with the ruggedness of the city. One of the most recognizable designs in the mini collection is the Sperry x PLEASURES 3-Eye Vibram Turn-Lock Lug Boat. The lug boat retains the classic shape of a boat shoe, but gets a revamp with supple leather inside and out. Fitted with the Vibram 884C Bristol Lake outsole for maximum traction, this sleek construction is redesigned with lace-free turn-lock dial closures.
Elsewhere, the Sperry x PLEASURES 3-Eye Vibram Hike reimagines everything you know about Sperry’s old-school style and transforms it into a hiker boot. Featuring a soft calf leather lining and insole for added comfort, the shoe dons the Vibram 639C Vybrid Hike outsole for durability and traction across any terrain. Rounding out the collection is the Sperry x PLEASURES 3-Eye Vibram Reflective Cold-Bay. Utilizing a reflective leather-and-rubber upper with Thinsulate insulation, this design marks an in-between point between the previous styles. Complete with a Vibram 262K New Bifida outsole, reflective hiker laces, and a leather insole, this shoe combines comfort, warmth, and style. All three designs will be released on November 18 via PLEASURES’ webstore and will also arrive at Sperry’s online store on November 19. The three designs range in price from $150 to $225.