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Cushioned Ankle Boots

1-36 of 56 results
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Cole Haan Rhinecliff Bootie (Women's)
Cole Haan Rhinecliff Bootie (Women's)
Cole Haan Rhinecliff Bootie (Women's)
New!
Sale
Cole Haan Rhinecliff Bootie(
                                      Women's) -
                                     Black Leather
Sale
Cole Haan Rhinecliff Bootie(
                                      Women's) -
                                     Sequoia Leather
Sale
$64.99
$198.00 67% off
Naturalizer Talley Ankle Boot (Women's)
Naturalizer Talley Ankle Boot (Women's)
Naturalizer Talley Ankle Boot (Women's)
Naturalizer Talley Ankle Boot (Women's)
New!
Sale
Naturalizer Talley Ankle Boot(
                                      Women's) -
                                     Black Oklahoma Leather
Sale
Naturalizer Talley Ankle Boot(
                                      Women's) -
                                     Classic Navy Suede/Bridle Brown Mirage
Sale
Naturalizer Talley Ankle Boot(
                                      Women's) -
                                     Dark Camel Suede/Bridle Brown Mirage
Sale
$99.99
$159.00 37% off
Naturalizer Elenor Ankle Boot (Women's)
Naturalizer Elenor Ankle Boot (Women's)
Naturalizer Elenor Ankle Boot (Women's)
Naturalizer Elenor Ankle Boot (Women's)
New!
Sale
Naturalizer Elenor Ankle Boot(
                                      Women's) -
                                     Black Sheep Premium Leather
Naturalizer Elenor Ankle Boot(
                                      Women's) -
                                     Bridle Brown Sheep Premium Leather
Naturalizer Elenor Ankle Boot(
                                      Women's) -
                                     Truffle Taupe Sheep Opera Leather
$118.95
Dr. Martens Jadon 8-Eye Boot
Dr. Martens Jadon 8-Eye Boot
Dr. Martens Jadon 8-Eye Boot
New!
Sale
Dr. Martens Jadon 8-Eye Boot -
                                     Black Polished Smooth
Dr. Martens Jadon 8-Eye Boot -
                                     Cherry Red Polished Smooth
$169.95
Carolinna Espinosa Toulee (Women's)
Carolinna Espinosa Toulee (Women's)
New!
Sale
Carolinna Espinosa Toulee(
                                      Women's) -
                                     Black Calf Leather
Sale
$108.97
$345.00 68% off
Naturalizer Jarrett Ankle Boot (Women's)
Naturalizer Jarrett Ankle Boot (Women's)
Naturalizer Jarrett Ankle Boot (Women's)
Naturalizer Jarrett Ankle Boot (Women's)
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) -
                                     Classic Navy Oiled Suede/Brown Leather
Sale
Naturalizer Jarrett Ankle Boot(
                                      Women's) -
                                     Taupe Oiled Suede/Brown Leather
Sale
$114.99
$129.00 11% off
SoftWalk Ivanhoe (Women's)
SoftWalk Ivanhoe (Women's)
SoftWalk Ivanhoe (Women's)
SoftWalk Ivanhoe (Women's)
New!
Sale
SoftWalk Ivanhoe(
                                      Women's) -
                                     Black Veg Tumbled Leather
SoftWalk Ivanhoe(
                                      Women's) -
                                     Cognac Veg Tumbled Leather
SoftWalk Ivanhoe(
                                      Women's) -
                                     Pewter Antique Metallic Leather
$165.00
SoftWalk Hanover Boot (Women's)
SoftWalk Hanover Boot (Women's)
SoftWalk Hanover Boot (Women's)
SoftWalk Hanover Boot (Women's)
New!
Sale
SoftWalk Hanover Boot(
                                      Women's) -
                                     Black Soft Nappa Leather
SoftWalk Hanover Boot(
                                      Women's) -
                                     Cognac Soft Nappa Leather
SoftWalk Hanover Boot(
                                      Women's) -
                                     Dark Brown Soft Nappa Leather
$140.00
SoftWalk Rocklin Boot (Women's)
SoftWalk Rocklin Boot (Women's)
SoftWalk Rocklin Boot (Women's)
SoftWalk Rocklin Boot (Women's)
SoftWalk Rocklin Boot (Women's)
SoftWalk Rocklin Boot (Women's)
New!
Sale
SoftWalk Rocklin Boot(
                                      Women's) -
                                     Black Cow Suede Leather
SoftWalk Rocklin Boot(
                                      Women's) -
                                     Black Veg Tumbled Leather
SoftWalk Rocklin Boot(
                                      Women's) -
                                     Black/Tan Soft Tumbled Leather/Leopard
SoftWalk Rocklin Boot(
                                      Women's) -
                                     Dark Brown Veg Tumbled Leather
SoftWalk Rocklin Boot(
                                      Women's) -
                                     Graphite Cow Suede
$144.95 - $149.95
Aerosoles Confidential Suede Wedge Bootie (Women's)
Aerosoles Confidential Suede Wedge Bootie (Women's)
Aerosoles Confidential Suede Wedge Bootie (Women's)
Aerosoles Confidential Suede Wedge Bootie (Women's)
Aerosoles Confidential Suede Wedge Bootie (Women's)
New!
Sale
Aerosoles Confidential Suede Wedge Bootie(
                                      Women's) -
                                     Black Suede
Sale
Aerosoles Confidential Suede Wedge Bootie(
                                      Women's) -
                                     Dark Gray Suede
Sale
Aerosoles Confidential Suede Wedge Bootie(
                                      Women's) -
                                     Dark Green Suede
Sale
Aerosoles Confidential Suede Wedge Bootie(
                                      Women's) -
                                     Mid Brown Suede
Sale
$69.99
$130.00 46% off
Naturalizer Harding Ankle Boot (Women's)
Naturalizer Harding Ankle Boot (Women's)
Naturalizer Harding Ankle Boot (Women's)
Naturalizer Harding Ankle Boot (Women's)
New!
Sale
Naturalizer Harding Ankle Boot(
                                      Women's) -
                                     Black Safari Crust/Leopard Faux Pony
Sale
Naturalizer Harding Ankle Boot(
                                      Women's) -
                                     Black Safari Crust/Snake Print
Sale
Naturalizer Harding Ankle Boot(
                                      Women's) -
                                     Bridle Brown Safari Premium
Sale
$99.99
$169.00 - $179.00 up to 44% off
Drew Zippy (Women's)
Drew Zippy (Women's)
Drew Zippy (Women's)
New!
Sale
Drew Zippy(
                                      Women's) -
                                     Black Soft Nappa
Drew Zippy(
                                      Women's) -
                                     Brown Soft Nappa
$158.95
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
New!
Sale
Stacy Adams Astro 53404(
                                      Men's) -
                                     Black Smooth Leather
Stacy Adams Astro 53404(
                                      Men's) -
                                     Black Suede
Stacy Adams Astro 53404(
                                      Men's) -
                                     Brown Suede
Stacy Adams Astro 53404(
                                      Men's) -
                                     Gray Suede
Stacy Adams Astro 53404(
                                      Men's) -
                                     Sand Suede
$89.95
Eastland Lumber Up (Men's)
Eastland Lumber Up (Men's)
Eastland Lumber Up (Men's)
Eastland Lumber Up (Men's)
Eastland Lumber Up (Men's)
Eastland Lumber Up (Men's)
Eastland Lumber Up (Men's)
New!
Sale
Eastland Lumber Up(
                                      Men's) -
                                     Brown Leather/Sherpa
Eastland Lumber Up(
                                      Men's) -
                                     Brown Oiled Suede
Eastland Lumber Up(
                                      Men's) -
                                     Gray
Eastland Lumber Up(
                                      Men's) -
                                     Natural Leather
Eastland Lumber Up(
                                      Men's) -
                                     Olive Suede
Eastland Lumber Up(
                                      Men's) -
                                     Peanut Leather
$124.95
Aerosoles Tor Guide (Women's)
Aerosoles Tor Guide (Women's)
Aerosoles Tor Guide (Women's)
New!
Sale
Aerosoles Tor Guide(
                                      Women's) -
                                     Black Suede
Sale
Aerosoles Tor Guide(
                                      Women's) -
                                     Mid Brown Suede
Sale
$69.99
$99.00 29% off
Naturalizer Quintana Ankle Boot (Women's)
Naturalizer Quintana Ankle Boot (Women's)
Naturalizer Quintana Ankle Boot (Women's)
New!
Sale
Naturalizer Quintana Ankle Boot(
                                      Women's) -
                                     Black Sheep Premium Leather
Sale
Naturalizer Quintana Ankle Boot(
                                      Women's) -
                                     Brown Sheep Premium Leather
Sale
$99.99
$139.00 28% off
Propet Sidney (Women's)
Propet Sidney (Women's)
Propet Sidney (Women's)
New!
Sale
Propet Sidney(
                                      Women's) -
                                     Black Velour
Sale
Propet Sidney(
                                      Women's) -
                                     Cigar Velour
Sale
$48.95
$59.95 18% off
Trotters Ladue (Women's)
Trotters Ladue (Women's)
Trotters Ladue (Women's)
Trotters Ladue (Women's)
Trotters Ladue (Women's)
New!
Sale
Trotters Ladue(
                                      Women's) -
                                     Black Veg Tumbled Leather
Sale
Trotters Ladue(
                                      Women's) -
                                     Cognac Veg Tumbled Leather
Sale
Trotters Ladue(
                                      Women's) -
                                     Dark Brown Nubuck/Textured Leather
Sale
Trotters Ladue(
                                      Women's) -
                                     Graphite/Dark Grey Nubuck/Textured Leather
Sale
$148.95
$165.00 10% off
Eastland 1955 Edition Sherman 1955 (Men's)
Eastland 1955 Edition Sherman 1955 (Men's)
Eastland 1955 Edition Sherman 1955 (Men's)
Eastland 1955 Edition Sherman 1955 (Men's)
New!
Sale
Eastland 1955 Edition Sherman 1955(
                                      Men's) -
                                     Black Leather
Eastland 1955 Edition Sherman 1955(
                                      Men's) -
                                     Dark Tan Leather
Eastland 1955 Edition Sherman 1955(
                                      Men's) -
                                     Oak Leather
$209.95
Aerosoles First Plan Quilted Suede Wedge Ankle Boot (Women's)
Aerosoles First Plan Quilted Suede Wedge Ankle Boot (Women's)
Aerosoles First Plan Quilted Suede Wedge Ankle Boot (Women's)
Aerosoles First Plan Quilted Suede Wedge Ankle Boot (Women's)
New!
Sale
Aerosoles First Plan Quilted Suede Wedge Ankle Boot(
                                      Women's) -
                                     Black Combo
Sale
Aerosoles First Plan Quilted Suede Wedge Ankle Boot(
                                      Women's) -
                                     Black Leather
Sale
Aerosoles First Plan Quilted Suede Wedge Ankle Boot(
                                      Women's) -
                                     Dark Brown Combo
Sale
$79.99
$99.00 19% off
Naturalizer Transform Ankle Boot (Women's)
Naturalizer Transform Ankle Boot (Women's)
Naturalizer Transform Ankle Boot (Women's)
Naturalizer Transform Ankle Boot (Women's)
New!
Sale
Naturalizer Transform Ankle Boot(
                                      Women's) -
                                     Dark Brown Sargeno Polyurethane
Sale
Naturalizer Transform Ankle Boot(
                                      Women's) -
                                     Dark Taupe Sargeno Polyurethane/Microfiber
Sale
Naturalizer Transform Ankle Boot(
                                      Women's) -
                                     Jet Black Sargeno Polyurethane
Sale
$69.99
$99.00 29% off
Eastland Seneca (Women's)
Eastland Seneca (Women's)
Eastland Seneca (Women's)
New!
Sale
Eastland Seneca(
                                      Women's) -
                                     Bomber Brown Leather
Eastland Seneca(
                                      Women's) -
                                     Natural Leather
$99.95
Drew Keith (Men's)
Drew Keith (Men's)
Drew Keith (Men's)
New!
Sale
Drew Keith(
                                      Men's) -
                                     Black Leather
Drew Keith(
                                      Men's) -
                                     Brandy Leather
$189.95
Cole Haan Indiana Short Waterproof Boot (Women's)
Cole Haan Indiana Short Waterproof Boot (Women's)
Cole Haan Indiana Short Waterproof Boot (Women's)
New!
Sale
Cole Haan Indiana Short Waterproof Boot(
                                      Women's) -
                                     Black
Sale
Cole Haan Indiana Short Waterproof Boot(
                                      Women's) -
                                     Chestnut
Sale
$139.95
$198.00 29% off
Dockers Vonner (Men's)
Dockers Vonner (Men's)
New!
Sale
Dockers Vonner(
                                      Men's) -
                                     Red Brown Oiled Distressed Full Grain Leather
Sale
$74.99
$90.00 17% off
Florsheim Hifi Moc Boot (Men's)
Florsheim Hifi Moc Boot (Men's)
Florsheim Hifi Moc Boot (Men's)
New!
Sale
Florsheim Hifi Moc Boot(
                                      Men's) -
                                     Brown Crazy Horse Leather
Florsheim Hifi Moc Boot(
                                      Men's) -
                                     Mushroom Suede
Sale
$97.95 - $109.95
$110.00 up to 11% off