Sperry x PLEASURES Collection Releases November 2025

Sperry and PLEASURES are joining forces once again, unveiling a three-shoe collection that redefines the brand’s nautical legacy through a modern, subcultural lens. The Los Angeles-based label injects its signature rebellious energy into Sperry’s heritage silhouettes, blending American craftsmanship with a street-ready edge.

Each pair pushes beyond traditional boat-shoe boundaries while keeping the rugged functionality that defines Sperry. The lineup features three distinct styles:

The Sperry x PLEASURES 3-Eye Vibram Hiker leads the collection with a durable Vibram sole and premium leather upper designed to handle any terrain. The Sperry x PLEASURES 3-Eye Vibram Turn-Lock Lug Boat swaps traditional laces for a mechanical turn-lock closure, offering a futuristic, lace-free fit that modernizes the classic boat silhouette. Rounding out the trio, the Sperry x PLEASURES 3-Eye Vibram Reflective Cold-Bay introduces reflective paneling and insulated construction for cold-weather comfort, fusing performance and bold visual flair.

The campaign, shot in a raw industrial setting, mirrors the collection’s spirit — grounded in craft, elevated by attitude. Each pair is equipped with heavy-duty Vibram outsoles for maximum grip and longevity, while weather-resistant uppers and thick rope-style laces enhance the functional-meets-fashion aesthetic.

Dropping first on November 18, 2025, via pleasuresnow.com, and later on November 19 through sperry.com, the collaboration marks another evolution of Sperry’s recent reinvention — one that welcomes grit, rebellion, and the unpredictable energy of the modern street scene.