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Gold Cup™ Harpswell Venetian Driver Loafer Dark Brown
- $33.59
$74.99- $33.59
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More sizes availableSet 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...- $33.59
$74.99- $33.59
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Gold1eyevib Dark Brown Men's Leather
- $33.50
$74.50- $33.50
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More sizes availableA handsome, luxurious take on our iconic Authentic Original boat shoe. The Gold Cup Authentic Original 1-Eye Vibram Wedge boat shoe is handcrafted to an exacting standard using premium full grain leather, copper hardware and sumptuous lamskin linings. The refined upper sits atop a...- $33.50
$74.50- $33.50
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Gold Cup™ Made in Maine Penny Loafer
- $61.99
$220.59- $61.99
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More sizes availableA luxurious take on the classic penny loafer, proudly handcrafted in Maine using the finest materials. The Made in Maine mens' Penny Loafer features a soft and smooth leather upper crafted using handsewn moccasin construction, with traditional penny loafer detailing on the tongue. These...- $61.99
$220.59- $61.99
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Gdbillfishpw Medium Beige Men's Gold Cup™ Luxury
- $29.00
$60.50- $29.00
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More sizes availableClassic style inspired by sport vibes. Made with a premium nubuck upper from a gold-rated tannery and perforated side panels, the Billfish™ 3-Eye Boat Shoe gives you the comfort and support of a sneaker with the stylings of a boat shoe. Material: Premium, Gold-rated,...- $29.00
$60.50- $29.00
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Gold Cup™ Billfish Penny Loafer
- $46.50
$128.99- $46.50
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More sizes availableDesigned to get better with wear, the Gold Cup Billfish Penny Slip-On is built to last. Inspired by our iconic boat shoe, this sporty, casual style is crafted using premium materials and a keen attention to detail. Made from the supplest leather, our finest...- $46.50
$128.99- $46.50
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Gold Cup™ Billfish Penny Loafer
- $45.59
$126.99- $45.59
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More sizes availableDesigned to get better with wear, the Gold Cup Billfish Penny Slip-On is built to last. Inspired by our iconic boat shoe, this sporty, casual style is crafted using premium materials and a keen attention to detail. Made from the supplest leather, our finest...- $45.59
$126.99- $45.59
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Gdharpswel1e Medium Beige Men's Gold Cup™ Luxury
- $33.59
$75.00- $33.59
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More sizes availableOur 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...- $33.59
$75.00- $33.59
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Gdbillfishpw Black Men's Gold Cup™ Luxury
- $24.00
$48.50- $24.00
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More sizes availableClassic style inspired by sport vibes. Made with a premium nubuck upper from a gold-rated tannery and perforated side panels, the Billfish™ 3-Eye Boat Shoe gives you the comfort and support of a sneaker with the stylings of a boat shoe. Material: Premium, Gold-rated,...- $24.00
$48.50- $24.00
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Goldboatwasv Light Brown Men's Gold Cup™ Luxury
- $48.00
$133.99- $48.00
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More sizes availableOur Gold Cup™ Boat Shoe absorbs the effects of shock by up to 30% for superior comfort. And with ultra-soft lambskin inside and 18K gold-plated eyelets outside, well—there’s your shock factor. Premium full-grain leather upper. Rawhide laces with our 360° Lacing System™ technology for...- $48.00
$133.99- $48.00
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Cambridge Tan Men's Leather
- $45.59
$126.99- $45.59
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More sizes availableMeticulously 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...- $45.59
$126.99- $45.59
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Goldboatwasv Amaretto Men's Gold Cup™ Luxury
- $48.50
$134.59- $48.50
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More sizes availableOur Gold Cup™ Boat Shoe absorbs the effects of shock by up to 30% for superior comfort. And with ultra-soft lambskin inside and 18K gold-plated eyelets outside, well—there’s your shock factor. Premium full-grain leather upper. Rawhide laces with our 360° Lacing System™ technology for...- $48.50
$134.59- $48.50
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Gcpennywoven Tan Men's Leather
- $50.00
$139.00- $50.00
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More sizes availableA luxe leather loafer, crafted to an unflinching Gold Cup-standard, for those who appreciate the finer things in life. The mens' Gold Cup Penny Loafer is crafted from premium woven leather with classic penny loafer detailing, for a look that's timeless but imbued with...- $50.00
$139.00- $50.00
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Gdbillfishpw Dark Brown Men's Gold Cup™ Luxury
- $24.50
$48.99- $24.50
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More sizes availableClassic style inspired by sport vibes. Made with a premium nubuck upper from a gold-rated tannery and perforated side panels, the Billfish™ 3-Eye Boat Shoe gives you the comfort and support of a sneaker with the stylings of a boat shoe. Material: Premium, Gold-rated,...- $24.50
$48.99- $24.50
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Gold Cup™ Harpswell Venetian Driver Loafer Charcoal
- $33.59
$74.59- $33.59
- Unit price
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More sizes availableSet 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...- $33.59
$74.59- $33.59
- Unit price
- per
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Gdharpswelvn Medium Beige Men's Gold Cup™ Luxury
- $46.00
$128.00- $46.00
- Unit price
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More sizes availableOur 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...- $46.00
$128.00- $46.00
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Authentic Original™ Mini Lug Captain's Oxford Amaretto
- $36.99
$82.00- $36.99
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More sizes availableThe mens' Topsider Mini Lug Captain's Oxford is the perfect shoe to bring a touch of sophistication to your fall looks. Crafted from premium leather, these smart lace ups are rooted in prepwear tradition and feature mocassin stitching construction. The timeless upper sits atop...- $36.99
$82.00- $36.99
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Authentic Original™ Harbor Loafer Other Brown
- $34.99
$82.99- $34.99
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More sizes availableAnchored in nautical tradition and crafted for days and nights spent ashore, the Authentic Original™ Harbor Penny Loafer is a smart choice for loafer lovers. Crafted from premium leather with traditional moccasin construction, these loafers bring a preppier look our iconic boat shoe silhouette....- $34.99
$82.99- $34.99
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Authentic Original™ Mini Lug Captain's Oxford Tan
- $37.50
$83.00- $37.50
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More sizes availableThe mens' Topsider Mini Lug Captain's Oxford is the perfect shoe to bring a touch of sophistication to your fall looks. Crafted from premium leather, these smart lace ups are rooted in prepwear tradition and feature mocassin stitching construction. The timeless upper sits atop...- $37.50
$83.00- $37.50
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Authentic Original™ Chukka Boot Light Brown
- $26.59
$53.00- $26.59
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More sizes availableThe Authentic Original™ Double Sole Chukka offers a bold new take on a coastal classic. Our iconic Authentic Original™ boat shoe upper has been reimagined as a mid-cut chukka, crafted from premium leather, with traditional moccasin construction. The preppy upper sits atop a double...- $26.59
$53.00- $26.59
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Authentic Original™ Venetian Loafer
- $34.59
$82.59- $34.59
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More sizes availableSlip into the men’s Authentic Original™ Venetian Heritage Loafer to experience the best in comfort and elevated casual style. Crafted from supple leather, it features EVA cushioning and our signature razor-cut Wave-Siping™ outsole for supreme comfort and confidence with every step. Wherever your day...- $34.59
$82.59- $34.59
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Saltwater 2.0 Duck Boot Black
- $20.00
$36.50- $20.00
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More sizes available
Reworked, reimagined and ready to handle whatever Mother Nature throws your way, the Saltwater 2.0 is the ultimate boot for your fall and winter adventures. This water-resistant boot features a premium leather upper, with a rubber duck shell that sits atop a raised rubber...
- $20.00
$36.50- $20.00
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Newton 3 Eye Lug Boat Shoe | Sperry Boat Shoes
- $37.99
$105.00- $37.99
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More sizes available
Add an extra dose of preppy style to your footwear collection with the double welt detailing and contrast rawhide lacing of the men’s Newton Authentic Original™ 3-Eye Boat Shoe. With a traction-enhancing Wave-Siping™ outsole and memory foam insole, this leather upper wardrobe essential is...
- $37.99
$105.00- $37.99
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Leather lotion No Colour Unisex Socks, Laces & Shoe Care
- $7.59
$11.59- $7.59
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More sizes available
Reinvent your favorite boat shoes with a Sperry colored lace kit. Choose a classic colour for a fresh look or a colored, genuine raw hide laces allow you to make your mark on a classic American icon. Kit includes two 46 inch laces and...
- $7.59
$11.59- $7.59
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Gold Cup™ Billfish Boat Shoe | Sperry Boat Shoes
- $45.50
$126.50- $45.50
- Unit price
- per
More sizes available
Crafted to an exacting standard using premium materials, the Gold Cup Billfish Plushwave is a modern, elevated take on our iconic boat shoe. Featuring the supplest leather and our finest moccasin stitching, this shoe is built not only to last but to get better...
- $45.50
$126.50- $45.50
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Drizzle Chelsea Rain Boot
- $33.59
$74.99- $33.59
- Unit price
- per
More sizes available
Stay dry and stylish with the ladies' Drizzle Chelsea Rain Boot. These lightweight rain boots are crafted from rubber, for a fully-waterproof upper and feature molded Wave-Siping™ technology on the outsole, for grip in wet and dry conditions. These boots have a sleek, timeless...
- $33.59
$74.99- $33.59
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Dakota Mid Winter Boots
- $32.59
$68.00- $32.59
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More sizes available
From après-ski to jaunts around town, bear the elements in style all winter long with the ladies’ Dakota snow boot. Constructed with a waterproof leather upper, cold-rating to -20°C, and Sperry’s signature Wave-Siping™ for secure footing, this mid-shaft performance boot will keep you warm...
- $32.59
$68.00- $32.59
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