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    Cushioned Ankle Boots

    1-36 of 253 results
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    Dr. Martens Church Monkey Boot
    New!
    Sale
    Dr. Martens Church Monkey Boot -Black Kaya
    New
    Dr. Martens Church Monkey Boot -Tan Carpathian
    New
    Dr. Martens Church Monkey Boot -Navy Waterproof Hi Suede
    Sale
    Dr. Martens Church Monkey Boot -Black Ajax/Reflective Glassine
    Dr. Martens Church Monkey Boot -Black Vintage Smooth
    Dr. Martens Church Monkey Boot -Charro/Dark Brown Brando/Hi Suede WP
    Dr. Martens Church Monkey Boot -Oxblood Vintage Smooth
    Dr. Martens Church Monkey Boot -White Smooth
    $65.95 - $144.95
    $130.00 - $145.00 up to 49% off
    Dansko Mina Bootie (Women's)
    New!
    Sale
    Dansko Mina Bootie(Women's) -Red Oiled Leather
    Sale
    Dansko Mina Bootie(Women's) -Taupe Milled Nubuck
    Sale
    Dansko Mina Bootie(Women's) -Black Milled Nubuck
    $147.95 - $184.95
    $185.00 up to 20% off
    Naturalizer Jarrett Ankle Boot (Women's)
    New!
    Sale
    Naturalizer Jarrett Ankle Boot(Women's) -Black Classic Vintage Leather
    Sale
    Naturalizer Jarrett Ankle Boot(Women's) -Bridle Brown Classic Vintage Leather
    Sale
    Naturalizer Jarrett Ankle Boot(Women's) -Wine Leather
    Sale
    $89.99
    $129.00 30% off
    Naturalizer Elisabeth Bootie (Women's)
    New!
    Sale
    Naturalizer Elisabeth Bootie(Women's) -Black Leather
    Sale
    Naturalizer Elisabeth Bootie(Women's) -Graphite Leather
    Sale
    Naturalizer Elisabeth Bootie(Women's) -Oxford brown Leather
    Sale
    $49.95 - $79.99
    $119.00 up to 58% off
    Clarks Devington Hi Lace Up Ankle Boot (Men's)
    New!
    Sale
    Clarks Devington Hi Lace Up Ankle Boot(Men's) -Black Smooth Buffalo Leather
    Sale
    Clarks Devington Hi Lace Up Ankle Boot(Men's) -Tobacco Buffalo Leather
    Sale
    $79.99
    $115.00 30% off
    Dansko Lee Zip-Up Bootie (Women's)
    New!
    Sale
    Dansko Lee Zip-Up Bootie(Women's) -Black Nubuck
    Sale
    Dansko Lee Zip-Up Bootie(Women's) -Grey Nubuck
    Sale
    Dansko Lee Zip-Up Bootie(Women's) -Khaki Nubuck
    Sale
    $143.95
    $179.95 20% off
    Cole Haan Grantland Waterproof Chelsea Boot (Men's)
    New!
    Sale
    Cole Haan Grantland Waterproof Chelsea Boot(Men's) -Black Waterproof Leather
    Sale
    Cole Haan Grantland Waterproof Chelsea Boot(Men's) -Burnt Chili Waterproof Leather
    Sale
    Cole Haan Grantland Waterproof Chelsea Boot(Men's) -Woodbury Waterproof Leather
    Sale
    $180.95
    $240.00 25% off
    Naturalizer Fortunate Bootie (Women's)
    New!
    Sale
    Naturalizer Fortunate Bootie(Women's) -Black Suede
    Sale
    Naturalizer Fortunate Bootie(Women's) -Camelot Suede
    Sale
    $99.99
    $169.00 41% off
    Dansko Lola Chelsea Boot (Women's)
    New!
    Sale
    Dansko Lola Chelsea Boot(Women's) -Black Antiqued Calf
    Sale
    Dansko Lola Chelsea Boot(Women's) -Black Nubuck
    Sale
    Dansko Lola Chelsea Boot(Women's) -Sand Burnished Nappa
    Sale
    Dansko Lola Chelsea Boot(Women's) -Stone Burnished Nappa
    Sale
    Dansko Lola Chelsea Boot(Women's) -Taupe Burnished Nappa
    Sale
    $135.95
    $170.00 20% off
    Naturalizer Quineta Bootie (Women's)
    New!
    Sale
    Naturalizer Quineta Bootie(Women's) -Black Leather
    Sale
    Naturalizer Quineta Bootie(Women's) -Graphite Lead Nubuck
    Sale
    $99.99
    $129.00 22% off
    Cole Haan Grantland 6
    New!
    Sale
    Cole Haan Grantland 6
    Sale
    Cole Haan Grantland 6
    Sale
    Cole Haan Grantland 6
    Sale
    $187.95
    $250.00 25% off
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    Clarks Edgewick Mid Ankle Boot (Men's)
    Description:
    The Clarks Edgewick Mid Ankle Boot is a contemporary take on classic sneakers. The Cushion Soft™ technology and a removable OrthoLite® sheet footbed ensure a comfortable walking experience, and an EVA midsole offers excellent stress and impact resistance. Pair this ...
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    Description:
    Vintage looks and modern comfort are what make the Randol Ankle Boot a solid addition to any wardrobe. Mesh liningsMemory Foam insole shapes to foot for instant comfortFusion Footbed adds an extra layer of cushionFlexible construction Fit: True to Size ...
    The Naot Limba lace-up ankle boot's rugged good looks will spruce up any casual ensemble. Padded tongue and collarRemovable, anatomic ...
    Naot Limba Ankle Boot (Men's)
    Description:
    The Naot Limba lace-up ankle boot's rugged good looks will spruce up any casual ensemble. Padded tongue and collarRemovable, anatomic cork and latex footbed wrapped in suedeLightweight lug sole for long-lasting performance and excellent grip in cold weatherHandsewn strobel construction ...