Bootleggers

Fashion Boots

Showing 25–36 of 39 results


  • The British invasion brought us the chelsea boot, and then we amped it up with a rich, full grain leather upper, waterproof construction and our Peak-to-Pavement® rubber outsole. No matter where you’re playing today, our Phil adds rock star vibe to any adventure.

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  • This redesign of our best-selling style maintains the look you love, but adds improvements to the fit, comfort, and traction. A skate shoe with the support of a boot, the Phil Mid II WP features a waterproof leather upper, breathable linings, and the versatility to take on any urban or outdoor adventure.

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  • The Sofia Chelsea modernizes a classic style with an eye-catching mix of materials, textures and colors on its full grain leather and suede upper. Featuring waterproof construction, a PU & memory foam footbed, and our Peak-to-Pavement® outsole, this Chelsea is ready for whatever comes next.

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  • Inspired by the rugged wonders of Wild Sky, WA, the Wild Sky Mid combines premium leathers, heathered textiles, and a waterproof/breathable membrane to deliver a high-performance hiking sneaker with easy-going style. A lightweight EVA midsole and aggressive traction underfoot ensures you’ll be steady and comfortable on the most demanding terrain.

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  • Purchase a Bootlegger’s Gift Card today. Any amount available with a $25 minimum. Cards do not expire and there are no fees.

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  • The slip-on waterproof winter boot to keep by the door. Featuring 200g of KEEN.WARM insulation, environmentally preferred leather, and a snow-ready sole.

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    • Waterproof leather and performance mesh upper
    • Metal eyelets for added durability
    • Breathable textile lining
    • Thermal heat shield insole captures warmth
    • Compression-molded EVA midsole for cushioning
    • Keen.polar traction outsole for more grip on snow and ice
    • Non-marking multi-directional lugs for increased traction
    • 5mm Multi-directional lugs for traction
    • Stability shank delivers lightweight support
    • Keen.dry waterproof, breathable membrane
    • Keen.warm recycled PET insulation rated to -25°F/-32°C
    • Eco anti-odor for natural odor control
    • Environmentally preferred premium leather from LWG-certified tannery
    • Notch in back for achilles comfort
    • High-abrasion rubber tip for added durability and protection
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  • The Oboz Bridger 7″ boot is a great winter option for snowshoeing and other winter activities. With 200 grams of Freeze Guard insulation, you won’t overheat during high intensity activities or be cold in more casual outdoor pursuits.

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  • Adventure in rugged comfort and support with Skechers Relaxed Fit®: Relment – Daggett. This lace-up outdoor trail design features a water-repellent synthetic and mesh upper with a cushioned Skechers Air-Cooled Memory Foam® insole.

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  • Get ready for outdoor adventures wearing Skechers x John Deere: Rowood – Moss Burrow! This waterproof work boot features a durable Goodyear welt construction, leather upper with contrast woven Mossy Oak® camo print, and a cushioned Skechers Air-Cooled Memory Foam® insole.

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  • Get ready for outdoor adventures wearing Skechers x John Deere: Bowland – Rugged-Dozer! This lace-up boot features a synthetic upper with a John Deere tractor charm, second set of laces, and a cushioned Skechers Air-Cooled Memory Foam® insole.

    For youngsters dreaming of driving a tractor someday, Skechers x John Deere for kids has arrived. Your little one can ‘work’ alongside you in total comfort thanks to these fun mini-you styles.

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

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