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  • Deckside CVO Sneakers NavyDeckside CVO Sneakers Navy

    Deckside CVO Sneakers Navy

    A versatile sneaker, anchored in a traditional of coastal style. The Deckside CVO mens' sneaker is inspired by the original deck sneaker, first developed by Paul Sperry in 1935, with a chambray textile upper sitting atop a classic vulcanized rubber sole, with adaptive Wave-Siping™...
    $26.59
    $55.50
    $26.59
  • Striperiiba Navy Men's SneakersStriperiiba Navy Men's Sneakers

    Striperiiba Navy Men's Sneakers

    Laid back? Yes. Legit? Also yes. Our Striper II looks all summer-ready, with a relaxed beach-blanket vibe. Underneath the chill are no-nonsense specs: intense traction, vulcanized construction (read: insane durability), and breathable woven canvas. Legit is right.Breathable woven canvas with genuine rawhide laces for...
    $15.50
    $23.99
    $15.50
  • Classiccvo Navy Textile Woven Unisex SneakersClassiccvo Navy Textile Woven Unisex Sneakers

    Classiccvo Navy Textile Woven Unisex Sneakers

    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...
    $15.99
    $24.50
    $15.99
  • Classic CVO Sneaker BlackClassic CVO Sneaker Black

    Classic CVO Sneaker Black

    Developed in the 1930s by Paul Sperry, the Classic CVO was the first non-slip deck shoe, thanks to our now iconic razor-cut Wave-Siping™ sole. Crafted with a durable canvas or woven upper, a vulcanized rubber midsole, and a cushioned insole, this easy-going, timeless lace-up...
    $19.99
    $33.00
    $19.99
  • Deckside CVO Sneakers GreyDeckside CVO Sneakers Grey

    Deckside CVO Sneakers Grey

    A versatile sneaker, anchored in a traditional of coastal style. The Deckside CVO mens' sneaker is inspired by the original deck sneaker, first developed by Paul Sperry in 1935, with a chambray textile upper sitting atop a classic vulcanized rubber sole, with adaptive Wave-Siping™...
    $26.99
    $55.99
    $26.99
  • Striperiictx Black Unisex SneakersStriperiictx Black Unisex Sneakers

    Striperiictx Black Unisex Sneakers

    A must-have sneaker to add to your collection. The Striper II CVO Core SW Twill features a relaxed salt-washed twill upper and cotton laces for minimalist style. Plus, a hidden gore construction provides easy on/off convenience so you never miss a beat and molded...
    $15.99
    $24.50
    $15.99
  • Halyardcvost White Men's SneakersHalyardcvost White Men's Sneakers

    Halyardcvost White Men's Sneakers

    The classic CVO sneaker that looks perfectly worn in—and feels it, too. These canvas uppers are paired with a full-length memory foam footbed that will make you want to keep them for the long haul.v Materials: Full-length memory foam insoles provide comfort and arch...
    $17.00
    $28.50
    $17.00
  • Classiccvo White/Multi Unisex SneakersClassiccvo White/Multi Unisex Sneakers

    Classiccvo White/Multi Unisex Sneakers

    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...
    $15.50
    $23.99
    $15.50
  • Striperiibat Black Men's SneakersStriperiibat Black Men's Sneakers

    Striperiibat Black Men's Sneakers

    Laid back? Yes. Legit? Also yes. Our Striper II looks all summer-ready, with a relaxed beach-blanket vibe. Underneath the chill are no-nonsense specs: intense traction, vulcanized construction (read: insane durability), and breathable woven canvas. Legit is right.Breathable woven canvas with genuine rawhide laces for...
    $12.59
    $19.50
    $12.59
  • Davenport Pull Up Leather 1-Eye Driver BlackDavenport Pull Up Leather 1-Eye Driver Black

    Davenport Pull Up Leather 1-Eye Driver Black

    Classic style. Premium design. Ultimate comfort. The Davenport 1-Eye Pull-Up flaunts a rich, tumbled "pull-up" leather upper and a podded rubber outsole. A softer, smoother alternative to traditional leather, this shoe features Adaptive Wave-Siping™ technology and dual-density insoles, so you can stay comfortable and...
    $37.99
    $90.00
    $37.99
  • Classcaptoxf Green Unisex Loafers & OxfordsClasscaptoxf Green Unisex Loafers & Oxfords

    Classcaptoxf Green Unisex Loafers & Oxfords

    A classic from the Sperry archives, our 3-eye Captain's Oxford is the first casual shoe designed by  Paul Sperry in 1935. The handsewn moc-toe construction, and the classic Smked Elk Colorway  will make this shoe a standout favorite in your rotation. Genuine all leather upper allows...
    $20.00
    $36.59
    $20.00
  • Made in Maine Vibram Penny LoaferMade in Maine Vibram Penny Loafer

    Made in Maine Vibram 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...
    $62.50
    $222.99
    $62.50
  • Wave Venetian Driver TaupeWave Venetian Driver Taupe

    Wave Venetian Driver Taupe

    Perfect for days behind the wheel and days at sea alike, the Wavedriver is part boat shoe, part driving shoe. A handsewn leather upper, podded rubber outsole and molded Wave-Siping™ technology gives these a refined look with a touch of practical utility. Pair them...
    $28.59
    $59.59
    $28.59
  • Topsfieldpny Black Men's LeatherTopsfieldpny Black Men's Leather

    Topsfieldpny Black Men's Leather

    A classic that can be worn day after day, season after season. Our timeless Topsfield Penny Loafer is crafted from pure leather, with traditional penny loafer detailing and moccasin stitching on the upper. A memory foam insole and flexible rubber sole offer superior comfort...
    $36.99
    $81.99
    $36.99
  • Topsfieldpny Tan Men's LeatherTopsfieldpny Tan Men's Leather

    Topsfieldpny Tan Men's Leather

    A classic that can be worn day after day, season after season. Our timeless Topsfield Penny Loafer is crafted from pure leather, with traditional penny loafer detailing and moccasin stitching on the upper. A memory foam insole and flexible rubber sole offer superior comfort...
    $37.59
    $83.59
    $37.59
  • Sperry x Colbo Captain’s OxfordSperry x Colbo Captain’s Oxford

    Sperry x Colbo Captain’s Oxford

    Colbo’s take on the Captain’s Oxford is intuitively designed to honour its place in Sperry’s 90-year history, while infusing it with a distinctly earthy, grounded design ethos. Like a rich patina, this casual staple only grows better with every wear. All sizes are in...
    $61.99
    $221.50
    $61.99
  • Wave Venetian Driver Other BlackWave Venetian Driver Other Black

    Wave Venetian Driver Other Black

    Perfect for days behind the wheel and days at sea alike, the Wavedriver is part boat shoe, part driving shoe. A handsewn leather upper, podded rubber outsole and molded Wave-Siping™ technology gives these a refined look with a touch of practical utility. Pair them...
    $29.00
    $60.59
    $29.00
  • Billfish Slip-on LoaferBillfish Slip-on Loafer

    Billfish Slip-on Loafer

    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...
    $38.50
    $91.50
    $38.50
  • Davenport Venetian Driver Dark BrownDavenport Venetian Driver Dark Brown

    Davenport Venetian Driver Dark Brown

    Slip into a timeless classic style with the Davenport Venetian Loafer. Flaunting unlined full-grain leather upper, a podded rubber outsole, and Adaptive Wave-Siping™ technologies, you can stay comfortable, grounded, and stylish all day long. Our signature loafer silhouette. Material: Premium, unlined full-grain leather Sole:...
    $38.00
    $90.59
    $38.00
  • Billfish Slip-on LoaferBillfish Slip-on Loafer

    Billfish Slip-on Loafer

    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...
    $37.99
    $90.00
    $37.99