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    • Sale
      77

      Gold Cup™ Harpswell 2-Eye Driver – Premium Golf Club

      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...
      $50.00
      $92.91
      $50.00
      Unit price
      / per 
    • Sale
      3.53.5

      Gold Cup™ Harpswell Venetian Driver Loafer – Official Site

      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...
      $68.25
      $136.83
      $68.25
      Unit price
      / per 
    • Sale
      77

      Authentic Original™ 3-Eye Boat Shoe – Official Site | Classic & Iconic Style

      For those who value a classic aesthetic, the men’s Authentic Original™ 3-Eye boat shoe adds enduring style to any look. Upholding 90 years of Sperry heritage, it’s crafted with a smooth leather upper, traditional moccasin stitching, 360° Lacing™, and a razor-cut Wave-Siping™ outsole for...
      $48.00
      $89.49
      $48.00
      Unit price
      / per 
    • Sale
      77

      Top Sider CVO Sneaker – Official Site

      Introduced by Paul Sperry in 1935, the original canvas deck sneaker is still going strong. This Top-Sider CVO is crafted from lightweight, durable canvas, and a vulcanized rubber sole with razor-cut Wave-Siping™ technology for a solid grip on wet and dry surfaces. Dress up...
      $27.49
      $45.79
      $27.49
      Unit price
      / per 
    • Sale
      3.53.5

      Gold Cup™ Authentic Original™ 1-Eye Boat Shoe

      Our original boat shoe, handcrafted with luxurious materials and unrivalled attention to detail. The Gold Cup Authentic Original 1-Eye Boat Shoe represents the pinnacle of a tradition stretching back nine decades. Crafted from premium full grain leather with lambskin lining, these boat shoes feature...
      $60.00
      $112.25
      $60.00
      Unit price
      / per 
    • Sale
      77

      Havasu Sport Sandal

      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...
      $12.99
      $19.31
      $12.99
      Unit price
      / per 
    • Sale
      77

      Newman Oxford II

      $32.48
      $57.65
      $32.48
      Unit price
      / per 
    • Sale
      77

      Hull 3 Eye Boat Shoe – Classic Men's Nautical Footwear

      The men’s Hull 3-Eye delivers its refined take on our iconic boat shoe. Crafted with traditional moccasin stitching, its premium leather and mixed material upper reads as a hybrid boat shoe. Featuring our 360° Lacing™ for a customizable fit, and a traction-enhancing Wave-Siping™ outsole,...
      $27.49
      $45.89
      $27.49
      Unit price
      / per 
    • Sale
      77

      Baitfish Thong Sandal

      Add the Baitfish Thong Sandal to your warm weather wardrobe to level up your casual style. So much better than a standard flip-flop, this shoe gets the Sperry treatment with premium full-grain leather, an EVA cushioning midsole and our signature molded Wave-Siping™ outsole to...
      $20.99
      $32.91
      $20.99
      Unit price
      / per 
    • Sale
      77

      Baitfish Thong Sandal

      Add the Baitfish Thong Sandal to your warm weather wardrobe to level up your casual style. So much better than a standard flip-flop, this shoe gets the Sperry treatment with premium full-grain leather, an EVA cushioning midsole and our signature molded Wave-Siping™ outsole to...
      $20.99
      $33.19
      $20.99
      Unit price
      / per 
    • Sale
      77

      CVO Helm Sneaker – Official Brand

      Born in 1935, the CVO lace-up quickly became the official footwear of the US Navy’s casual uniform. This CVO Helm offers refreshed styling and the comfort features you’ve come to love including a removable insole and molded outsole with Wave-Siping™ technology. Featuring goes-with-everything great...
      $38.25
      $69.77
      $38.25
      Unit price
      / per 
    • Sale
      77

      Authentic Original™ 2-Eye Woven Boat Shoe – Sperry

      Our classic boater serves up a fashionable twist in this ladies' Authentic Original™ 2-Eye Woven Boat Shoe. 360° Lacing™ provides an adjustable fit, while a Wave-Siping™ outsole makes it anti-slip. Its moccasin-stitched premium leather upper features woven leatherwork for eye-catching texture and breathability, making...
      $36.00
      $64.22
      $36.00
      Unit price
      / per 
    • Sale
      77

      Mini Lug 3-Eye Boat Shoe – Official Site | Classic & Durable

      A fresh take on the classic boat shoe, the men’s Mini Lug 3-Eye combines smooth leather with moccasin stitching and Sperry’s signature 360° Lacing System™. A cushioned EVA insole offers all-day comfort while a rubber mini lug outsole adds a little edge, making it...
      $56.00
      $104.20
      $56.00
      Unit price
      / per 
    • Sale
      77

      Slim Boat Shoe – Classic Slip-On Casual Footwear for Men and Women

      Our iconic boat shoe has been reimagined with a slimmer, more modern silhouette. The men’s Slim Boat Shoe features all our famous detailing, including 360° Lacing™ for an adjustable fit and Wave-Siping™ outsoles for enhanced traction. Pair this flattering streamlined style with shorts on...
      $27.49
      $45.80
      $27.49
      Unit price
      / per 
    • Sale
      77

      Smythe Duck Chukka Slip-On Shoes

      An everyday slip-on with a duck boot aesthetic, the Smythe Chukka by Sperry seamlessly blends casual style with reliable performance. Built with an Adaptive Wave-Siping™ outsole for a slip-free grip on wet or dry surfaces and an EVA cushioning insole for elevated comfort, this...
      $32.48
      $57.46
      $32.48
      Unit price
      / per 
    • Sale
      77

      Drake 1-Eye Duck Boot – Waterproof Leather & Rubber Winter Boot

      $35.98
      $64.96
      $35.98
      Unit price
      / per 
    • Sale
      77

      Baitfish Thong Sandal

      Add the Baitfish Thong Sandal to your warm weather wardrobe to level up your casual style. So much better than a standard flip-flop, this shoe gets the Sperry treatment with premium full-grain leather, an EVA cushioning midsole and our signature molded Wave-Siping™ outsole to...
      $20.99
      $33.00
      $20.99
      Unit price
      / per 
    • Sale
      77

      Authentic Original™ Venetian Loafer – Official Site | Classic Men's Shoes

      Slip 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...
      $46.20
      $87.53
      $46.20
      Unit price
      / per 
    • Sale
      77

      Gold Cup™ Harpswell Venetian Driver Loafer – Official Site

      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...
      $52.00
      $97.03
      $52.00
      Unit price
      / per 
    • Sale
      77

      Ventura Sandal

      Destined to become your favorite warm weather shoe, make sure the Ventura Sandal is part of your wardrobe. Its cushioned footbed ensures ultimate comfort while its quick on and off design delivers ease of wear. Plus, with its molded Wave-Siping™ sole, you can be...
      $12.99
      $19.10
      $12.99
      Unit price
      / per 
    • Sale
      77

      Ripple Resort Boat Shoe – Official Site | Comfortable & Stylish

      $32.49
      $57.53
      $32.49
      Unit price
      / per 
    • Sale
      77

      Authentic Original™ 2-Eye Cross Lace Boat Shoe – Sperry

      The classic silhouette you know and love gets an update with convenience in mind in this men’s Authentic Original™ 2-Eye Cross Lace Boat Shoe. EVA cushioning delivers comfort, a Wave-Siping™ outsole ensures a secure foothold, and crossed laces and hidden gore construction provide easy...
      $38.40
      $69.32
      $38.40
      Unit price
      / per 
    • Sale
      77

      Dipsail Mesh 3 Eye Boat Sneaker – Official Site

      $27.49
      $45.70
      $27.49
      Unit price
      / per 
    • Sale
      77

      Helm Lace to Toe Sneaker – Official Site | Men's & Women's Footwear

      With a classic CVO silhouette, the Helm LTT Leather Sneaker delivers refreshed styling and crafted details for a shoe that’s as timeless as it is comfortable. Its high-quality leather upper is paired with a vulcanized rubber sole featuring our famous Wave-Siping™ technology for stability...
      $30.00
      $53.24
      $30.00
      Unit price
      / per 
    • Sale
      3.53.5

      Gold Cup™ Authentic Original™ 2-Eye Boat Shoe

      Experience the finest expression of Sperry craftsmanship with the Gold Cup™ Authentic Original™ 2-Eye Boat Shoe. Handcrafted for men who appreciate exceptional quality, this iconic silhouette is elevated with luxurious materials, including premium full-grain leather in a versatile medium beige finish and a supple...
      $68.25
      $139.89
      $68.25
      Unit price
      / per 
    • Sale
      77

      Harpoon 3-Eye Boat Shoe

      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...
      $17.99
      $28.38
      $17.99
      Unit price
      / per 
    • Sale
      77

      Newman Oxford II

      $32.48
      $57.19
      $32.48
      Unit price
      / per 
    • Sale
      77

      Gold Cup™ Harpswell 2-Eye Driver – Premium Golf Club

      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...
      $50.00
      $92.69
      $50.00
      Unit price
      / per 
    • Sale
      77

      Authentic Original™ Mini Lug Captain's Oxford

      Say aye aye to sophisticated style with the men’s Mini Lug Captain's Oxford. Crafted from premium leather with moccasin stitching, this smart lace-up is rooted in preppy tradition to elevate your looks for any season. The timeless upper features 360° Lacing™ for an adjustable...
      $56.00
      $103.30
      $56.00
      Unit price
      / per 
    • Sale
      Tan3.5

      Gold Cup™ Woven Penny Loafer – Official Site | Classic Men's Shoes

      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...
      $64.00
      $134.02
      $64.00
      Unit price
      / per 
    Showing 31 -60 of 216 total
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