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Chelsea Boots

Chelsea Boots

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  • 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
  • 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 Other BrownColdbay Slip-on Duck Shoes Other Brown

    Coldbay Slip-on Duck Shoes Other 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...
    $35.50
    $88.00
    $35.50