Products

Meticulously crafted to the Gold Cup standard, the men’s Cambridge Penny Loafer features moccasin hand-stitching, premium leather uppers and a lambskin lining and insole for a refined touch, durability and ultimate comfort. Dressed up or down, this luxurious shoe will effortlessly elevate your look...

Elevate any outfit with the Gold Cup™ Cambridge Penny Loafer, a refined expression of Sperry craftsmanship. Designed with exceptional attention to detail, this timeless slip-on pairs premium leather with classic penny loafer styling for understated sophistication that complements both tailored and smart-casual looks. An...

Meticulously crafted to the Gold Cup standard, the men’s Cambridge Penny Loafer features moccasin hand-stitching, premium leather uppers and a lambskin lining and insole for a refined touch, durability and ultimate comfort. Dressed up or down, this luxurious shoe will effortlessly elevate your look...

Meticulously crafted to the Gold Cup standard, the men’s Cambridge Penny Loafer features moccasin hand-stitching, premium leather uppers and a lambskin lining and insole for a refined touch, durability and ultimate comfort. Dressed up or down, this luxurious shoe will effortlessly elevate your look...

A classic style icon is raised to the gold standard in this Gold Cup™ CVO Lace-Up. Made from the supplest leather using masterful craftsmanship, and featuring Wave-Siping™ for a solid grip and a removable insole for ultimate comfort, Sperry’s beloved sneaker silhouette is poised...

A classic style icon is raised to the gold standard in this Gold Cup™ CVO Lace-Up. Made from the supplest leather using masterful craftsmanship, and featuring Wave-Siping™ for a solid grip and a removable insole for ultimate comfort, Sperry’s beloved sneaker silhouette is poised...

Part boat shoe, part driving shoe, the ladies' Gold Cup Driver unites two legendary styles using the utmost of attention. Crafted to the highest standard, it features a sumptuously soft leather upper, thin metal-tipped rope laces, 360° Lacing™, and Wave-Siping™ technology for sure footing....

Part boat shoe, part driving shoe. The ladies' Gold Cup Driver brings together two legendary styles, crafted to the highest Gold Cup-standard. With a sumptuously soft tumbled leather upper and thin, metal-tipped rope laces, this sleek shoe offers a refined footwear option for any...

Part boat shoe, part driving shoe. The ladies' Gold Cup Driver brings together two legendary styles, crafted to the highest Gold Cup-standard. With a sumptuously soft tumbled leather upper and thin, metal-tipped rope laces, this sleek shoe offers a refined footwear option for any...

Go for the highest standards with the Gold Cup Harpswell 1-Eye Driving Moc. Handcrafted from premium leather, with rawhide laces, a luxurious lambskin lining and meticulous moccasin stitching, this stylish shoe sits atop a slim rubber outsole with traction-enahncing Wave-Siping™. When you accept only...

Designed using the supplest leather and the finest moccasin stitching, the Gold Cup™ Harpswell 2-Eye Driver Loafer sets you on the road in elevated style. Built to last, this testament to craftsmanship gets even better over time. Wave-Siping™ and 360° Lacing™ ensure ultimate comfort...

Designed using the supplest leather and the finest moccasin stitching, the Gold Cup™ Harpswell 2-Eye Driver Loafer sets you on the road in elevated style. Built to last, this testament to craftsmanship gets even better over time. Wave-Siping™ and 360° Lacing™ ensure ultimate comfort...

Designed using the supplest leather and the finest moccasin stitching, the Gold Cup™ Harpswell 2-Eye Driver Loafer sets you on the road in elevated style. Built to last, this testament to craftsmanship gets even better over time. Wave-Siping™ and 360° Lacing™ ensure ultimate comfort...

Set a new benchmark for luxury with the Gold Cup Harpswell Venetian Loafer. Handcrafted from premium leather, with a luxurious lambskin lining and meticulous moccasin stitching, this tasteful loafer sits atop a slim rubber outsole with traction-enhancing Wave-Siping™. Comfortable and classic, this shoe is...

Set a new benchmark for luxury with the Gold Cup Harpswell Venetian Loafer. Handcrafted from premium leather, with a luxurious lambskin lining and meticulous moccasin stitching, this tasteful loafer sits atop a slim rubber outsole with traction-enhancing Wave-Siping™. Comfortable and classic, this shoe is...

Our Gold Cup™ classic driving moccasin is a testament to craftsmanship and comfort that stands the test of time. It'll be smooth sailing from the moment you slip them on your feet. Perfect for enjoying your favorite recreational pastimes, it also works for business...

Set a new benchmark for luxury with the Gold Cup Harpswell Venetian Loafer. Handcrafted from premium leather, with a luxurious lambskin lining and meticulous moccasin stitching, this tasteful loafer sits atop a slim rubber outsole with traction-enhancing Wave-Siping™. Comfortable and classic, this shoe is...

Refined style starts with the Gold Cup™ Woven Penny Loafer, an elevated leather loafer designed for men who appreciate timeless sophistication and exceptional quality. Expertly made from premium woven leather with classic penny loafer detailing, this regular width slip-on brings effortless polish to business...

The men’s Harpoon Lace-Up is a modern, sporty take on our iconic boat shoe. Built for comfort, it features a breathable mixed material upper with 360° Lacing™, and a lightweight OrthoLite® insole that delivers long-term cushioning, fit and performance. This casual shoe easily completes...

The men’s Harpoon Lace-Up is a modern, sporty take on our iconic boat shoe. Built for comfort, it features a breathable mixed material upper with 360° Lacing™, and a lightweight OrthoLite® insole that delivers long-term cushioning, fit and performance. This casual shoe easily completes...

The men’s Harpoon Lace-Up is a modern, sporty take on our iconic boat shoe. Built for comfort, it features a breathable mixed material upper with 360° Lacing™, and a lightweight OrthoLite® insole that delivers long-term cushioning, fit and performance. This casual shoe easily completes...

The men’s Harpoon Lace-Up is a modern, sporty take on our iconic boat shoe. Built for comfort, it features a breathable mixed material upper with 360° Lacing™, and a lightweight OrthoLite® insole that delivers long-term cushioning, fit and performance. This casual shoe easily completes...

Step out in modern, sporty style with the men’s Harpoon Crush Slip-On. Built for comfort, it features a breathable mesh upper with 360° Lacing™, and a lightweight OrthoLite® insole that delivers long-term cushioning, fit and performance. This casual shoe easily completes all your laid-back...

Step out in modern, sporty style with the men’s Harpoon Crush Slip-On. Built for comfort, it features a breathable mesh upper with 360° Lacing™, and a lightweight OrthoLite® insole that delivers long-term cushioning, fit and performance. This casual shoe easily completes all your laid-back...

Soon to become the official shoe of all your warm weather outings, the Havasu Sport Sandal is here to perform. Designed for comfort, it features an EVA cushioned insole and a molded outsole with Wave-Siping™ technology for secure footing even on wet surfaces. Paired...

Soon to become the official shoe of all your warm weather outings, the Havasu Sport Sandal is here to perform. Designed for comfort, it features an EVA cushioned insole and a molded outsole with Wave-Siping™ technology for secure footing even on wet surfaces. Paired...

A sandal that puts comfort and convenience at the fore, with an eye towards performance, the men’s Havasu Sandal sees a perforated leather thong strap sit atop a cushioned sole with Wave-Siping™ that disperses water for superior traction and comfort. Wear it on deck,...

A sandal that puts comfort and convenience at the fore, with an eye towards performance, the men’s Havasu Sandal sees a perforated leather thong strap sit atop a cushioned sole with Wave-Siping™ that disperses water for superior traction and comfort. Wear it on deck,...

A boat shoe with a sneaker sensibility, the Helm 2-Eye is ready to join you on all your outings. Designed with supreme comfort and casual style in mind, this twill lace-up shoe features 360° Lacing™ for an adjustable fit and a molded Wave-Siping™ outsole...

A boat shoe with a sneaker sensibility, the Helm 2-Eye is ready to join you on all your outings. Designed with supreme comfort and casual style in mind, this twill lace-up shoe features 360° Lacing™ for an adjustable fit and a molded Wave-Siping™ outsole...