Leather Ankle Boots
Leather ankle boots bring timeless style and dependable comfort to any wardrobe. Whether you're heading out for a day in town or exploring the outdoors, these versatile boots are designed to fit seamlessly into your everyday routine. With classic looks that never go out of style and quality craftsmanship you can count on, leather ankle boots are an effortless choice for everything from casual outings to more polished occasions. Find the pair that’s just right for you and enjoy lasting value with every step.
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Men's Bean Boots, 10" Shearling-Lined Tumbled Leather
A Maine-made boot with tumbled leather, shearling lining, and waterproof rubber bottom for cold, wet conditions.
Pros: High quality Waterproof Well-made Warmth Soft fabric
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Men's Bean Boots, 8" Shearling-Lined Insulated
A Maine-made boot with plush shearling lining, waterproof leather, and reliable traction for cold conditions.
Pros: High durability Waterproof quality Made in the USA Excellent warmth Comfortable fit
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Men's Bean Boots, 6.5" Chelsea
A black leather and rubber Chelsea boot with waterproof bottom, soft tumbled upper, and reliable traction.
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Women's Teva Anaya Booties, Waterproof Side-Zip
A waterproof brown leather ankle boot with a side-zip, rubber outsole, and antimicrobial treatment for all-day comfort.
Pros: Perfect fit Good quality Holds up well in rain Warm and cozy Comfortable
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Men's Bucksport Boots, Cap Toe
A rugged coffee bean leather boot with Vibram® rubber outsoles and waterproof oiled-leather upper.
Pros: Quality construction Waterproof Great color High comfort Useful side pockets
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Men's Stonington Chelsea Boots, Leather
A rugged dark oakwood leather pull-on boot with sneaker-like comfort and durable VertiGrip rubber outsole.
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Men's Portland Boots, Chelsea
A heritage-inspired leather Chelsea boot with elastic goring and a durable Vibram® rubber outsole in dark russet.
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Women's Blundstone 9500 High Top Chelsea Boots
A versatile pair of rustic black leather Chelsea boots with cushioned insoles and non-slip polyurethane outsoles.
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Women's TOMS® Everly Chelsea Boots, Suede
An oatmeal suede leather ankle bootie with dual gore panels and a 2 3/4" stacked heel.
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Men's Portland Boots, Lace-Up
A heritage-inspired leather boot with a Vibram® rubber outsole, perfect for city exploration.
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Women's Stonington Chelsea Boots, Leather
A rugged dark oakwood leather chelsea boot with sneaker-like comfort and durable rubber outsole.
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Women's Bean Boots, 8" Shearling-Lined Insulated
A pair of tan and brown leather boots with plush shearling lining and waterproof rubber bottoms.
Pros: Waterproof Well-made Warmth Durable Comfortable
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Men's Storm Chaser Boots 5, Leather Lace-Up
A durable, waterproof leather boot with PrimaLoft insulation and EVA midsole for comfort in cold, wet conditions.
Pros: Perfect fit Quality craftsmanship Great color High comfort Excellent warmth
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Women's Stonington Boots, Moc Toe
A rugged black leather moc toe boot with sneaker-like comfort, waterproof protection, and durable rubber outsole.
Pros: Great fit Versatile Comfortable Well made Looks great
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Men's Kangaroo Upland Hunter's Boots, Insulated
An 8" brown leather hunting boot with 200-gram Primaloft insulation and Vibram Mega-Grip outsole.
Pros: No break-in period needed High-quality leather Great traction Comfortable fit Excellent warmth
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Men's Cresta II Waterproof Hiking Boots, Leather
A brown leather hiking boot with waterproof membrane, Vibram® sole, and cushioned EVA footbed for comfort.
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Women's Camden Hills Chelsea Boots
A stylish black Chelsea boot with full-grain leather, rubber outsole, and cushioned EVA footbed for comfort.
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Women's Camden Hills Alpine Boots
A rugged and stylish black alpine boot with full-grain leather, wool lining, and VertiGrip rubber outsole.
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Women's Camden Hills Boots, Lace-Up
A stylish and functional black lace-up boot with full-grain leather upper and durable rubber outsole.
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Men's Lodge Moc Vibram® Buckle Boots, Shearling
A brown full-grain leather boot with shearling lining, Vibram rubber sole, and adjustable buckle closure.
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Women's Cresta II Waterproof Hiking Boots, Leather
A brown leather hiking boot with waterproof membrane, cushioned EVA footbed, and Vibram rubber sole for traction.
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Women's Frye Kate Harness Boots
A brown premium leather pull-on boot featuring Frye's iconic harness detail and a cushioned insole.
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Women's Blundstone Heeled Chelsea Boots
A versatile black slip-on boot with a 2" heel, featuring weatherproof leather and a cushioned midsole.
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Women's Eco Bay Chukka Boots, Leather
A brown waterproof nubuck leather chukka boot with recycled materials and a grippy rubber outsole.
