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    • 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
      77

      Strake 2 Eye

      Crafted from high-quality leather, the mens' Strake 2-Eye Cup Sole is a sporty take on the classic boat shoe. Its cup sole with razor-cut Wave-Siping™ technology delivers traction on wet and dry surfaces, while its memory foam insole and 360° Lacing™ provide ultimate comfort...
      $21.99
      $36.78
      $21.99
      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

      Seasock™ II Water Shoe

      $32.50
      $57.33
      $32.50
      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
      SS

      Men's 3-Pack Arch Support Socks

      Built to keep you comfortable from morning to night, these socks pair moisture-wicking fabric with cushioned support for all-day wear. Whether you're breaking in new boat shoes or layering up for cooler days, they add just the right touch of warmth and style. A...
      $4.54
      $6.88
      $4.54
      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 
    • Sale
      3.53.5

      Classic CVO Sneaker – Official Brand Name | Shop Now

      The original canvas deck sneaker that started it all. When Paul Sperry slipped off his boat, the Sirocco, in the early 1930’s, Sperry found inspiration in the natural texture of his dog Prince’s footpads, which never seemed to slip, even on ice. Cutting patterned...
      $27.49
      $45.97
      $27.49
      Unit price
      / per 
    • Sale
      77

      Billfish™ Slip-on Loafer – Comfortable & Stylish Men's Slip-On Shoes

      The mens' Billfish Slip-On sees our iconic boat shoe reimagined with an emphasis on comfort and convenience. A sportier silhouette is crafted from premium leather, with mesh panelling for breathability, a full-length cushioned midsole for superior comfort and support, and our famous Wave-Siping™ outsole...
      $35.98
      $64.07
      $35.98
      Unit price
      / per 
    • Sale
      3.53.5

      Sea Kite Sport Moc Boat Shoe – Official Site | Shop Now

      Our original leather boat shoe meets our performance water sneaker. The Sea Kite Moc is durable, reliable, and always ready to set sail. Its molded EVA midsole minimizes the impact of the sea and a non-marking rubber outsole with Adaptive Wave Siping™ technology enhances...
      $36.00
      $63.99
      $36.00
      Unit price
      / per 
    • Sale
      77

      Authentic Original™ 2-Eye Lug Boat Shoe – Official Sperry

      Inject rugged appeal into your wardrobe with Sperry’s Authentic Original™ 2-Eye Lug Sole Boat Shoe. Its nubuck upper features moccasin stitching and a 360° Lacing System™, while its sole features our famous Wave-Siping™ technology for secure footing in wet or dry conditions. This everyday...
      $56.00
      $103.57
      $56.00
      Unit price
      / per 
    • Sale
      77

      Sperry x Mifland Billfish

      The Billfish offers a modern, more athletic interpretation of one of Sperry’s core styles – and a longtime favorite of Mifland founder, Tobi Egberongbe. Designed to reflect the colorful and playful nature of the Mifland brand, each foot features different-colored suede panels for an...
      $45.00
      $83.29
      $45.00
      Unit price
      / per 
    • Sale
      3.53.5

      Wave Venetian Driver – Official Brand Name & Product Keywords

      Wanted: Sleek drivers only. The Wave Venetian Driver is all that and more with genuine hand-sewn construction for all day function and style.
      $46.20
      $85.85
      $46.20
      Unit price
      / per 
    • Sale
      77

      Authentic Original™ 1-Eye Boat Shoe – Classic Style & Premium Comfort

      Our iconic Authentic Original™ Boat Shoe has defined coastal style for generations. Here, the legendary silhouette is crafted from premium leather in smart shades, with traditional moccasin construction, an adjustable 360° Lacing System™ and our signature razor-cut Wave-Siping™ outsole for superior traction. With their...
      $35.98
      $64.34
      $35.98
      Unit price
      / per 
    • Sale
      77

      Slim Boat Shoe – Classic Slip-On Casual Footwear

      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
      $45.92
      $27.49
      Unit price
      / per 
    • Sale
      SS

      Men's 3-Pack Ankle Socks

      Built to keep you comfortable from morning to night, these socks pair moisture-wicking fabric with cushioned support for all-day wear. Whether you're breaking in new boat shoes or layering up for cooler days, they add just the right touch of warmth and style. A...
      $8.45
      $12.97
      $8.45
      Unit price
      / per 
    • Sale
      77

      Billfish™ 3-Eye Boat Shoe – Classic Nautical Style & Comfort

      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...
      $36.00
      $64.87
      $36.00
      Unit price
      / per 
    • Sale
      77

      CVO Max Sneaker – Official Brand

      Inspired by Paul Sperry’s iconic 1970s Circular Vamp Oxford, the CVO Max carries forward the original look that won over generations. Featuring a cushioned comfort insole and the same trusted molded Wave-Siping™ outsole and classic design, it’s reimagined for today for even more comfort...
      $46.20
      $87.73
      $46.20
      Unit price
      / per 
    • Sale
      77

      Authentic Original™ 2-Eye Boat Shoe – Official Site | Classic Style & Premium Comfort

      Our most iconic silhouette, the Authentic Original™ 2-Eye Boat Shoe stands out for its superior craftsmanship and attention to detail. It features traditional moccasin construction, 360° Lacing™ for a snug fit, EVA cushioning for ultimate comfort and our famous razor-cut Wave-Siping™ outsole for stability...
      $46.20
      $86.76
      $46.20
      Unit price
      / per 
    • Sale
      77

      Authentic Original™ 2-Eye Boat Shoe – Official Site | Classic Style & Premium Comfort

      Our most iconic silhouette, the Authentic Original™ 2-Eye Boat Shoe stands out for its superior craftsmanship and attention to detail. It features traditional moccasin construction, 360° Lacing™ for a snug fit, EVA cushioning for ultimate comfort and our famous razor-cut Wave-Siping™ outsole for stability...
      $27.49
      $48.80
      $27.49
      Unit price
      / per 
    • Sale
      77

      Authentic Original™ 2-Eye Lite Boat Shoe – Sperry

      Crafted from high-quality textile, the ladies’ Authentic Original™ 2-Eye Lite Boat Shoe delivers a lightweight twist on our iconic leather style. Comfort features include an EVA cushioned insole, 360° Lacing™ for a custom fit, and a molded Wave-Siping™ outsole for enhanced traction. This shoe...
      $27.50
      $48.67
      $27.50
      Unit price
      / per 
    • Sale
      3.53.5

      Authentic Original™ 2-Eye Boat Shoe – Official Site | Classic Style & Premium Comfort

      Our most iconic silhouette, the Authentic Original™ 2-Eye Boat Shoe stands out for its superior craftsmanship and attention to detail. It features traditional moccasin construction, 360° Lacing™ for a snug fit, EVA cushioning for ultimate comfort and our famous razor-cut Wave-Siping™ outsole for stability...
      $46.20
      $87.16
      $46.20
      Unit price
      / per 
    • Sale
      77

      Coastal CVO Crush Sneaker – Official Brand

      Whether you crush down its collapsible heel for quick sprints to the dock or lace it up as a traditional sneaker for outings in town, the CVO Coastal Crush Back Lace-Up has perfected two-way wear. Comes with two pairs of laces and an elastic...
      $21.99
      $36.57
      $21.99
      Unit price
      / per 
    • Sale
      77

      Sperry x Todd Snyder x Mister Rogers' Neighborhood CVO Sneaker Reissue

      Inspired by Mister Rogers’ enduring warmth and approachability to American style, the Sperry x Todd Snyder x Mister Rogers Neighborhood collaboration reimagines Top-Siders through a nostalgic lens. First introduced in 1935 and made iconic by figures like Mister Rogers, the 70s re-issue CVO comes...
      $48.00
      $89.79
      $48.00
      Unit price
      / per 
    • Sale
      77

      Authentic Original™ 1-Eye Boat Shoe – Official Site | Classic Style & Premium Comfort

      Our iconic Authentic Original™ Boat Shoe has defined coastal style for generations. Here, the legendary silhouette is crafted from premium leather with traditional moccasin construction, an adjustable 360° Lacing System™, EVA cushioning and our signature razor-cut Wave-Siping™ outsole for superior traction. Wear this men’s...
      $29.99
      $53.20
      $29.99
      Unit price
      / per 
    • Sale
      77

      Billfish™ Slip-on Loafer – Official Site | Comfortable Men's Casual Shoes

      Embrace the lace-less life and step out in style with this men's Billfish Slip-On shoe. The perfect finishing touch to so many casual outfits, its leather and mixed material upper, removable insole, and molded Wave-Siping™ outsole make your comfort their mission so you can...
      $31.49
      $55.50
      $31.49
      Unit price
      / per 
    • Sale
      77

      CVO Helm Sneaker – Official Site

      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
      $70.35
      $38.25
      Unit price
      / per 
    Showing 61 -90 of 260 total
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