Sperry and PLEASURES Turn the Tide on Classic Icons
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By PAGE Editor
Sperry and PLEASURES have reunited for their second collaboration, launching a bold three-shoe capsule that pushes the boundaries of classic nautical style by injecting a gritty, subcultural edge. The collection sees PLEASURES take three unique Sperry silhouettes to another level, resulting in a striking fusion of classic Americana and rebellion that pushes Sperry’s DNA into unexpected, uncharted waters.
The capsule features three distinct designs: the Sperry x PLEASURES 3-Eye Vibram® Reflective Cold-Bay, the Sperry x PLEASURES 3-Eye Vibram® Turn-Lock Lug Boat, and the Sperry x PLEASURES 3-Eye Vibram® Hiker. Melding exemplary design with an attitude of defiance, each pair is crafted from premium leathers and suedes, while Sperry’s iconic sail logo is reinterpreted through the distinctive PLEASURES lens.
The collection’s inspiration draws from a shared appreciation for the boat shoe and PLEASURES Co-Founder Alex James’ roots in New York and New Jersey’s alternative music scenes—a defining chapter that continues to influence his creative direction.
“This collaboration has always been about reimagining something timeless through a subcultural lens,” says Alex James, Co-Founder of PLEASURES. “Sperry has such a rich heritage, while PLEASURES brings bold, raw energy. Together, we’ve created something that’s both nostalgic and radically new.”
This sentiment is echoed by Sperry’s leadership, who see the partnership as a key to evolving the brand. “Our partnership with PLEASURES continues to challenge what Sperry can represent,” says Jonathan Frankel, President of Sperry. “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.”
A Closer Look at the Capsule:
Sperry x PLEASURES 3-Eye Vibram® Hiker: Crafted from premium leather, this shoe combines elevated materials with rugged functionality. It features a soft calf leather lining and insole for comfort, while the Vibram® 629C Vybrid Hike outsole ensures durability and grip across varied terrain.
Sperry x PLEASURES 3-Eye Vibram® Turn-Lock Lug Boat: This design reimagines the classic boat shoe with modern precision. Crafted from supple leather inside and out, it features a Vibram® 884C Bristol Lake outsole for superior traction and a lace-free turn-lock dial closure, giving the silhouette a sleek, innovative construction.
Sperry x PLEASURES 3-Eye Vibram® Reflective Cold-Bay: This 3-Eye shoe pairs a reflective leather-and-rubber upper with Thinsulate insulation and a leather insole for warmth and comfort. A Vibram® 262K New Bifida outsole ensures traction, while reflective hiker laces, and a secondary lace option, add versatile style.
The campaign for the collection was captured during the winemaking process at Avenales Ranch. Amid the vineyards and rolling, oak-filled hills of California, the radical styling of the Sperry x PLEASURES Collection stands out against the earthy, open landscape, highlighting the unexpected dialogue between high-tech design and legacy craftsmanship.
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