Bootleggers Footwear

Women's Boots

Showing 13–24 of 35 results


  • Michele is a Chelsea boot inspired by our equestrian heritage, designed for all your meaningful pursuits. Crafted from beautiful waxy leathers that only get better with age, developing a rich premium look over time. Built with all-day comfort and support, this boot is as durable and stylish as it is versatile, perfect for whatever your day brings.

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  • This performance bootie is made with tough jobs and long days in mind. Slip-resistant support will help you keep your footing all day long.

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  • Inspired by the iconic Chore Boot, the Women’s Originals Ankle waterproof outdoor boot is a lightweight, 6” essential designed for everyday comfort, protection, and dependable performance in wet conditions.

    Built with a 100% waterproof and 100% Muckproof full neoprene bootie, it delivers flexible comfort while keeping feet dry through rain, mud, and outdoor work. Soft hand-laid rubber wraps the boot for added durability and protection without sacrificing comfort or ease of movement.

    Underfoot, a molded PU footbed with memory foam cushioning provides long-lasting comfort and support, while bioDEWIX™ Dry with NZYM™ technology helps control odor and moisture to keep feet feeling fresher throughout the day.

    The durable rubber outsole features an innovative lug design that delivers reliable traction while quickly shedding mud and debris for cleaner, more stable steps. The exposed neoprene sides improve flexibility and make the boot easy to slip on and off.

    From gardening and yard work to dog walking, outdoor chores, and wet-weather errands, the Women’s Originals Ankle waterproof work boot is built for everyday versatility, comfort, and protection.

    Select options This product has multiple variants. The options may be chosen on the product page
  • Discover the perfect blend of style and functionality with the everyday Kora boot. Embrace your wanderlust and make every day an adventure in these must-have boots!

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  • The Shelby boot is designed with a waterproof PU upper, waterproof membrane, and sealed seams to help keep moisture out. Inside, a soft padded insole and cozy short faux-fur lining and footbed provide warmth and comfort with every step. Finished with a durable rubber outsole for reliable traction and everyday wear, these boots are a practical and stylish choice for wet and chilly weather.

    Select options This product has multiple variants. The options may be chosen on the product page
  • Look and feel your best, even in the worst weather, in these gorgeous Italian leather boots.

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  • Look and feel your best, even in the worst weather, in these gorgeous Italian leather boots.

    Select options This product has multiple variants. The options may be chosen on the product page
  • Fresh autumn slip on boots crafted with unique charm and character.

    Softly structured and incredibly comfortable, our mid-height Tabitha boot makes a casual-cool statement in rich, hand-finished leathers.

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  • Fresh autumn slip on boots crafted with unique charm and character.

    Softly structured and incredibly comfortable, our mid-height Tabitha boot makes a casual-cool statement in rich, hand-finished leathers.

    Select options This product has multiple variants. The options may be chosen on the product page
  • Everyday Ease, Everywhere You Go.
    A relaxed waterproof chukka born from the Caribou™ and built to keep up. Crafted in soft supple leather and lined with faux shearling, it delivers all-day comfort and adaptable style—just as ready for après-ski as it is for city streets or cross-country travel.

    Select options This product has multiple variants. The options may be chosen on the product page
  • Unconditional Style.
    Unshakeable and iconic. With full-grain leather or wool-like felted uppers and waterproof construction, this duck boot holds its ground in all conditions.

    Select options This product has multiple variants. The options may be chosen on the product page
  • Unconditional Style.
    Unshakeable and iconic. With full-grain leather or wool-like felted uppers and waterproof construction, this duck boot holds its ground in all conditions.

    Select options This product has multiple variants. The options may be chosen on the product page

Showing 13–24 of 35 results

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