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Looking to treat that special someone in your life to the understated luxury look, or just want to treat yourself? Look no further than the Sperry Gold Cup collection. Made with premium materials and high-end comfort in mind, these styles are living large – and, by definition, you are too. Check out the list below for our recommendations of the best Gold Cup styles on our website right now.

Authentic Original Rivingston Boat Shoe

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Boat shoe? More like yacht shoe! Meet the boat shoe that has major swag factor. With an ultra-soft lambskin lining and next-level cushioning underfoot, The Authentic Original Rivingston Boat Shoe is a luxe, multi-tone take on our classic boat shoe. The Rivingston features a shock-absorbing heel cup and an Ortholite® insole for supreme comfort, while style accents like 18k gold-plated eyelets (in select styles) and rich, full grain burnished leather built for comfort and classic luxe style.


Handcrafted in Maine Authentic Original Boat Shoe


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Made in New England never looked so good. Our Handcrafted in Maine Authentic Original is an exclusive member of the Gold Cup collection built on old world tanning techniques, one-of-a kind stitching, and the added layer of New England artisanal shoemaking tradition. Each pair is slightly different, and each has its own character, born of the artisan’s hands. Steeped in history and handcrafted in Maine, these boat shoes are hand-sewn and feature premium Vibram® outsoles for optimum comfort, traction, and durability.


Striper PLUSHWAVE™ CVO Sneaker

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The most comfortable version of the sneaker that started it all. Step into the best of the best with the Gold Cup Striper PLUSHWAVE™ CVO Sneaker. This casual but elegant sneaker flaunts an ultrasoft full-grain leather upper and our signature PLUSHWAVE™ technology for maximum comfort.


Harpswell 1-Eye Driver

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The Gold Cup Harpswell 1-Eye Driver is a testament to craftsmanship and comfort that stands the test of time. With our patented Anti-Shock and Vibration technology™, it’ll be smooth sailing from the moment you slip them on your feet. This classic driving moccasin is the perfect versatile footwear option for the professional on the go, great for enjoying favorite recreational pastimes and for business casual wear.


Authentic Original PLUSHWAVE™ 2-Eye Boat Shoe

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The Gold Cup Authentic Original PLUSHWAVE™ 2-Eye Boat Shoe is soft, sleek, and waterproof. Flaunting premium materials like nubuck and lambskin and featuring a subtle, criss-cross lace, this style elevates any outfit. Plus, our top-of-the-line PLUSHWAVE™ technology significantly increases comfort, making every step feel light as air.




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