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    Gold Cup™

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    • Sale
      Gold1eyevib Dark Brown Men's LeatherGold1eyevib Dark Brown Men's Leather

      Gold1eyevib Dark Brown Men's Leather

      A 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...
      $33.59
      $74.99
      $33.59
      Unit price
      / per 
    • Sale
      Gold Cup™ Made in Maine Penny LoaferGold Cup™ Made in Maine Penny Loafer

      Gold Cup™ Made in Maine Penny Loafer

      A 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...
      $63.00
      $225.50
      $63.00
      Unit price
      / per 
    • Sale
      Gdbillfishpw Medium Beige Men's Gold Cup™ LuxuryGdbillfishpw Medium Beige Men's Gold Cup™ Luxury

      Gdbillfishpw Medium Beige Men's Gold Cup™ Luxury

      Classic 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,...
      $28.99
      $60.00
      $28.99
      Unit price
      / per 
    • Sale
      Gold Cup™ Billfish Penny LoaferGold Cup™ Billfish Penny Loafer

      Gold Cup™ Billfish Penny Loafer

      Designed 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...
      $45.50
      $126.00
      $45.50
      Unit price
      / per 
    • Sale
      Gold Cup™ Billfish Penny LoaferGold Cup™ Billfish Penny Loafer

      Gold Cup™ Billfish Penny Loafer

      Designed 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
      Unit price
      / per 
    • Sale
      Gdharpswel1e Medium Beige Men's Gold Cup™ LuxuryGdharpswel1e Medium Beige Men's Gold Cup™ Luxury

      Gdharpswel1e Medium Beige Men's Gold Cup™ Luxury

      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...
      $33.99
      $75.50
      $33.99
      Unit price
      / per 
    • Sale
      Gdbillfishpw Black Men's Gold Cup™ LuxuryGdbillfishpw Black Men's Gold Cup™ Luxury

      Gdbillfishpw Black Men's Gold Cup™ Luxury

      Classic 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
      Unit price
      / per 
    • Sale
      Goldboatwasv Light Brown Men's Gold Cup™ LuxuryGoldboatwasv Light Brown Men's Gold Cup™ Luxury

      Goldboatwasv Light Brown Men's Gold Cup™ Luxury

      Our 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...
      $49.00
      $136.59
      $49.00
      Unit price
      / per 
    • Sale
      Cambridge Tan Men's LeatherCambridge Tan Men's Leather

      Cambridge Tan Men's Leather

      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...
      $45.50
      $126.50
      $45.50
      Unit price
      / per 
    • Sale
      Goldboatwasv Amaretto Men's Gold Cup™ LuxuryGoldboatwasv Amaretto Men's Gold Cup™ Luxury

      Goldboatwasv Amaretto Men's Gold Cup™ Luxury

      Our 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...
      $48.99
      $135.99
      $48.99
      Unit price
      / per 
    • Sale
      Gcpennywoven Tan Men's LeatherGcpennywoven Tan Men's Leather

      Gcpennywoven Tan Men's Leather

      A 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...
      $49.59
      $137.99
      $49.59
      Unit price
      / per 
    • Sale
      Gdbillfishpw Dark Brown Men's Gold Cup™ LuxuryGdbillfishpw Dark Brown Men's Gold Cup™ Luxury

      Gdbillfishpw Dark Brown Men's Gold Cup™ Luxury

      Classic 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
      $48.59
      $24.50
      Unit price
      / per 
    • Sale
      Gold Cup™ Harpswell Venetian Driver Loafer CharcoalGold Cup™ Harpswell Venetian Driver Loafer Charcoal

      Gold Cup™ Harpswell Venetian Driver Loafer Charcoal

      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...
      $33.50
      $74.50
      $33.50
      Unit price
      / per 
    • Sale
      Gdharpswelvn Medium Beige Men's Gold Cup™ LuxuryGdharpswelvn Medium Beige Men's Gold Cup™ Luxury

      Gdharpswelvn Medium Beige Men's Gold Cup™ Luxury

      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...
      $45.50
      $126.00
      $45.50
      Unit price
      / per 
    • Sale
      Authentic Original™ Mini Lug Captain's Oxford AmarettoAuthentic Original™ Mini Lug Captain's Oxford Amaretto

      Authentic Original™ Mini Lug Captain's Oxford Amaretto

      The 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...
      $37.59
      $83.59
      $37.59
      Unit price
      / per 
    • Sale
      Sperry x Colbo Authentic Original™ Boat ShoeSperry x Colbo Authentic Original™ Boat Shoe

      Sperry x Colbo Authentic Original™ Boat Shoe

      Material: Leather Boat Shoe Round Toe Flat Heel 360° Lacing System™ technology for a customized fit Heel Height: 0.75"
      $49.99
      $151.50
      $49.99
      Unit price
      / per 
    • Sale
      Authentic Original™ 2-Eye Lite Boat Shoe lite Black Men's MenAuthentic Original™ 2-Eye Lite Boat Shoe lite Black Men's Men

      Authentic Original™ 2-Eye Lite Boat Shoe lite Black Men's Men

      Crafted from high-quality textile, the men’s Authentic Original™ 2-Eye Lite Boat Shoe delivers a lightweight twist on our iconic leather style. Comfort features include an EVA cushioning insole, 360° Lacing™ for a custom fit, and a molded Wave-Siping™ outsole for enhanced traction. This shoe...
      $19.99
      $33.00
      $19.99
      Unit price
      / per 
    • Sale
      Billfish 3-Eye Boat Shoe Tan - 2Billfish 3-Eye Boat Shoe Tan - 2

      Billfish 3-Eye Boat Shoe Tan - 2

      A sporty, modern take on our iconic boat shoe, the Billfish is equipped to handle everything life–and the sea–throws at you. These reimagined boat shoes are made with luxurious nubuck, mesh panelling and our classic moccasin stitching, with a full-length cushioned midsole and a...
      $37.99
      $90.00
      $37.99
      Unit price
      / per 
    • Sale
      Authentic Original™ 3 Eye Mini Lug Boat ShoeAuthentic Original™ 3 Eye Mini Lug Boat Shoe

      Authentic Original™ 3 Eye Mini Lug Boat Shoe

      A stylish and fresh take on our iconic boat shoe, the mens' Mini Lug 3-Eye Topsider brings a bold touch to any outfit. Crafted from premium leather, with moccasin stitching around the toe and stitched detailing across the side panelling, these boat shoes feature...
      $29.00
      $60.59
      $29.00
      Unit price
      / per 
    • Sale
      Authentic Original™ 2-Eye Lace Boat Shoe Other BlackAuthentic Original™ 2-Eye Lace Boat Shoe Other Black

      Authentic Original™ 2-Eye Lace Boat Shoe Other Black

      The mens' Authentic Original™ 2-Eye Cross Lace is perfect for those who prefer sleek footwear to round out their looks. These shoes feature our iconic Authentic Original™ boat shoe upper, crafted from premium leather, with traditional moccasin stitching construction. A sleek, streamlined cross lace...
      $26.59
      $53.00
      $26.59
      Unit price
      / per 
    Showing 1 -20 of 33 total
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