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  • Newman Chukka Boot BrownNewman Chukka Boot Brown

    Newman Chukka Boot Brown

    It’s hard to find anything more versatile than a water-resista+M984:W984nt leather chukka boot. Wear it in all conditions with waxed jackets and khakis, or sweatshirts and denim. Characterful details like a nautical print lining and a stitched welt round out its appeal. Water-resistant leather...
    $32.99
    $78.50
    $32.99
  • Newton Heritage Chukka Boot TanNewton Heritage Chukka Boot Tan

    Newton Heritage Chukka Boot Tan

    A Chukka boot with boat shoe detailing, the men’s Newton Lug Boot offers the best of both aesthetics. Sperry’s traction-enhancing Wave-Siping™ sole lets you step out in stylish confidence, while its rich leather upper, moccasin stitching, and rawhide laces create a timeless silhouette that...
    $41.99
    $116.00
    $41.99
  • Newman Chukka Boot Medium BeigeNewman Chukka Boot Medium Beige

    Newman Chukka Boot Medium Beige

    It’s hard to find anything more versatile than a water-resista+M984:W984nt leather chukka boot. Wear it in all conditions with waxed jackets and khakis, or sweatshirts and denim. Characterful details like a nautical print lining and a stitched welt round out its appeal. Water-resistant leather...
    $33.50
    $79.59
    $33.50
  • Tour Moc Mid Top Sneaker BlackTour Moc Mid Top Sneaker Black

    Tour Moc Mid Top Sneaker Black

    Smart and timeless, the Topsider Tour Mid Moc is a versatile boot that can be worn day in, day out, whether you're exploring, heading out to dinner or heading into work. Crafted from premium leather, these mid-cut ankle boots are a sleek take on...
    $37.50
    $82.99
    $37.50
  • Tour Moc Mid Top Sneaker TanTour Moc Mid Top Sneaker Tan

    Tour Moc Mid Top Sneaker Tan

    Smart and timeless, the Topsider Tour Mid Moc is a versatile boot that can be worn day in, day out, whether you're exploring, heading out to dinner or heading into work. Crafted from premium leather, these mid-cut ankle boots are a sleek take on...
    $37.50
    $82.99
    $37.50
  • Newton Heritage Chukka Boot TaupeNewton Heritage Chukka Boot Taupe

    Newton Heritage Chukka Boot Taupe

    A Chukka boot with boat shoe detailing, the men’s Newton Lug Boot offers the best of both aesthetics. Sperry’s traction-enhancing Wave-Siping™ sole lets you step out in stylish confidence, while its rich leather upper, moccasin stitching, and rawhide laces create a timeless silhouette that...
    $42.50
    $118.00
    $42.50
  • Fenway Pull-on Chelsea Boots BrownFenway Pull-on Chelsea Boots Brown

    Fenway Pull-on Chelsea Boots Brown

    A must-have for any modern man’s wardrobe, the Fenway Pull-On ankle boot delivers classic Chelsea appeal. Pull tabs and elasticized paneling make it quick and convenient to slip on and off while water-resistance and Sperry’s signature Wave-Siping™ outsole help you face the wet or...
    $41.50
    $103.50
    $41.50
  • Fenway Pull-on Chelsea Boots Dark BrownFenway Pull-on Chelsea Boots Dark Brown

    Fenway Pull-on Chelsea Boots Dark Brown

    A must-have for any modern man’s wardrobe, the Fenway Pull-On ankle boot delivers classic Chelsea appeal. Pull tabs and elasticized paneling make it quick and convenient to slip on and off while water-resistance and Sperry’s signature Wave-Siping™ outsole help you face the wet or...
    $41.99
    $104.59
    $41.99
  • Fenway BootsFenway Boots

    Fenway Boots

    The perfect complement to your cool-weather wardrobe, the men’s Fenway lace-up features moccasin construction and sleek metal eyelets for a rugged yet polished aesthetic. Waterproof, warm-lined, and outfitted with a traction-enhancing Wave-Siping™ outsole, this leather ankle boot will keep you warm, dry, and looking...
    $36.99
    $82.00
    $36.99
  • Tour Moc Mid Top Sneaker Dark BrownTour Moc Mid Top Sneaker Dark Brown

    Tour Moc Mid Top Sneaker Dark Brown

    Smart and timeless, the Topsider Tour Mid Moc is a versatile boot that can be worn day in, day out, whether you're exploring, heading out to dinner or heading into work. Crafted from premium leather, these mid-cut ankle boots are a sleek take on...
    $37.00
    $82.59
    $37.00
  • Fenway BootsFenway Boots

    Fenway Boots

    The perfect complement to your cool-weather wardrobe, the men’s Fenway lace-up features moccasin construction and sleek metal eyelets for a rugged yet polished aesthetic. Waterproof, warm-lined, and outfitted with a traction-enhancing Wave-Siping™ outsole, this leather ankle boot will keep you warm, dry, and looking...
    $37.00
    $82.59
    $37.00
  • Stringer Boot TanStringer Boot Tan

    Stringer Boot Tan

    The mens' Stringer Lug Chukka is the ultimate boot to ace cold weather style. Constructed using traditional moccasin stitching techniques, the upper is crafted from luxurious leather with contrast detailing, and rawhide leather laces. A rugged lug sole provides grip in changing weather and...
    $32.99
    $68.59
    $32.99
  • Stringer Boot Dark BrownStringer Boot Dark Brown

    Stringer Boot Dark Brown

    The mens' Stringer Lug Chukka is the ultimate boot to ace cold weather style. Constructed using traditional moccasin stitching techniques, the upper is crafted from luxurious leather with contrast detailing, and rawhide leather laces. A rugged lug sole provides grip in changing weather and...
    $32.59
    $68.50
    $32.59
  • Nortfolk Boot BrownNortfolk Boot Brown

    Nortfolk Boot Brown

    The mens' Norfolk Boot offers a refined yet utilitarian option for cold, wet days. Done up in smart shades, the Norfolk's rounded chukka upper is waterproof, providing comfort and style in equal measure. A molded Wave-Siping™ sole ensures superior traction in wet and dry...
    $25.00
    $45.99
    $25.00
  • Gloucester Duck Boots Other BlackGloucester Duck Boots Other Black

    Gloucester Duck Boots Other Black

    The mens' Gloucester Cold Bay Boots are ready to handle all of your cold weather adventures. Designed with warmth and comfort in mind, these mid-rise ankle boots are waterproof and outfitted with a thermal lining, in addition to a duck boot-style rubber guard around...
    $33.00
    $69.00
    $33.00
  • Ice Bay Chukka BootIce Bay Chukka Boot

    Ice Bay Chukka Boot

    Looking for style and substance in your cold-weather footwear? The men’s Ice Bay Tall Boot will surpass your expectations. Featuring waterproofing, cold rating to -20°C, and Sperry’s famous Wave-Siping™ outsole for secure footing on wet or dry surfaces, this winterized version of our classic...
    $28.59
    $59.99
    $28.59
  • Avenue Duck Boot Black for Men's | Duck & Rain BootsAvenue Duck Boot Black for Men's | Duck & Rain Boots

    Avenue Duck Boot Black for Men's | Duck & Rain Boots

    Don’t let cold temperatures and stormy skies stop you from embarking on your next journey. Take on the elements in Sperry boots designed to withstand wet weather and rugged terrain. Our two-tone men's Sperry duck boots are built with essential features and quality materials...
    $17.00
    $28.50
    $17.00
  • Clifton Boot OliveClifton Boot Olive

    Clifton Boot Olive

    Don't let the weather put a damper on your sense of style with the mens' Coldbay Clifton Boot. With a waterproof rubber upper, these slip-on boots feature duck boot detailing on the toe and covenient elastic panelling at the ankle to make them easy...
    $30.59
    $63.99
    $30.59
  • Cutwater Deck Boot Navy - 2Cutwater Deck Boot Navy - 2

    Cutwater Deck Boot Navy - 2

    A modern waterproof Chelsea boot, anchored in a sea-faring tradition and crafted for the demands of modern sailing. The Cutwater Deck Chelsea Boot features quick-drying perforated neoprene ankle panelling that offers breathability, with a rubber upper providing protection from water. Pull tabs at both...
    $25.00
    $45.59
    $25.00
  • Coldbay Slip-on Duck Shoes BrownColdbay Slip-on Duck Shoes Brown

    Coldbay Slip-on Duck Shoes Brown

    The Coldbay Duck Boot is a coastal classic, ensuring you're ready for colder weather for years to come. With a premium leather upper and a classic rubber duck shell, these boots have a timeless look rooted in preppy traditions. The waterproof upper and thermal...
    $33.50
    $74.00
    $33.50