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Cushioned $65 - $100 Chelsea Boots

Skechers Relaxed Fit Rolden Warton Chelsea Boot (Men's)
New!
Sale
Skechers Relaxed Fit Rolden Warton Chelsea Boot(Men's) -Dark Brown
Sale
$76.95
$85.00 9% off
Dr. Martens Work Hardie Low Cut Chelsea Boot (Men's)
New!
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Dr. Martens Work Hardie Low Cut Chelsea Boot(Men's) -Black Pit Quarter Full Grain Leather
Dr. Martens Work Hardie Low Cut Chelsea Boot(Men's) -Whiskey Pit Quarter Full Grain Leather
Sale
$79.95
$90.00 11% off
Dr. Martens Work Penly Low Cut Utility Chelsea Boot (Men's)
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Dr. Martens Work Penly Low Cut Utility Chelsea Boot(Men's) -Black Greenland Full Grain Leather
Sale
$91.95 - $114.95
$125.00 up to 26% off
Cougar Kensington Waterproof Chelsea Boot (Women's)
New!
Sale
Cougar Kensington Waterproof Chelsea Boot(Women's) -Black Rubber
New
Cougar Kensington Waterproof Chelsea Boot(Women's) -Blossom Rubber
New
Cougar Kensington Waterproof Chelsea Boot(Women's) -Black/White Rubber
Cougar Kensington Waterproof Chelsea Boot(Women's) -Dove Rubber
Cougar Kensington Waterproof Chelsea Boot(Women's) -Mist Rubber
Cougar Kensington Waterproof Chelsea Boot(Women's) -Nude Rubber
New
Cougar Kensington Waterproof Chelsea Boot(Women's) -Plum Synthetic Rubber
Cougar Kensington Waterproof Chelsea Boot(Women's) -Silver Metallic Synthetic Rubber
Cougar Kensington Waterproof Chelsea Boot(Women's) -Tropical Floral Rubber
Cougar Kensington Waterproof Chelsea Boot(Women's) -Walnut Synthetic Rubber
$69.95
Skechers Relaxed Fit Molton Gaveno Chelsea Boot (Men's)
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Skechers Relaxed Fit Molton Gaveno Chelsea Boot(Men's) -Black
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Skechers Relaxed Fit Molton Gaveno Chelsea Boot(Men's) -Brown
Sale
$90.95
$105.00 13% off
Bogs Overcast Chelsea Rainboot (Men's)
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Sale
Bogs Overcast Chelsea Rainboot(Men's) -Black Rubber
New
Bogs Overcast Chelsea Rainboot(Men's) -Gray Rubber
New
Bogs Overcast Chelsea Rainboot(Men's) -Olive Rubber
New
$69.95
ECCO Crepetray Chelsea Boot (Men's)
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ECCO Crepetray Chelsea Boot(Men's) -Cocoa Brown Suede
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ECCO Crepetray Chelsea Boot(Men's) -Tarmac Suede
Sale
$81.95 - $89.95
$200.00 up to 59% off
Florsheim Estabrook Gore Boot (Men's)
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Sale
Florsheim Estabrook Gore Boot(Men's) -Brown Crazy Horse Leather
Sale
$89.95
$125.00 28% off
Dr. Martens Zillow Chelsea Boot (Women's)
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Sale
Dr. Martens Zillow Chelsea Boot(Women's) -Cherry Red Antique Temperley Full Grain Leather
Sale
$76.95 - $134.95
$135.00 - $145.00 up to 47% off
Nunn Bush Otis Plain Toe Chelsea Boot (Men's)
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Nunn Bush Otis Plain Toe Chelsea Boot(Men's) -Black Tumble Leather
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Nunn Bush Otis Plain Toe Chelsea Boot(Men's) -Brown Chamois Leather
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Nunn Bush Otis Plain Toe Chelsea Boot(Men's) -Rust Leather
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Nunn Bush Otis Plain Toe Chelsea Boot(Men's) -Tan Chamois Leather
Sale
$74.95
$95.00 21% off
Naturalizer Femma Ankle Boot (Women's)
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Naturalizer Femma Ankle Boot(Women's) -Alabaster Pebbled Leather
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Naturalizer Femma Ankle Boot(Women's) -Black Leather
Sale
$99.99
$130.00 23% off
Rocky Lakeland Twin Gore Outdoor Chelsea Boot RKS0362 (Men's)
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Sale
Rocky Lakeland Twin Gore Outdoor Chelsea Boot RKS0362(Men's) -Brown Full Grain Leather
Sale
$99.99
$119.99 17% off
Clarks Clarkdale Arlo Chelsea Boot (Women's)
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Sale
Clarks Clarkdale Arlo Chelsea Boot(Women's) -Burgundy Suede
Sale
$84.95
$160.00 47% off
UGG Faye Chelsea Boot (Women's)
New!
Sale
UGG Faye Chelsea Boot(Women's) -Tideline Suede
Sale
$82.95
$160.00 48% off
Mark Nason Los Angeles Tamar Chelsea Boot (Men's)
New!
Sale
Mark Nason Los Angeles Tamar Chelsea Boot(Men's) -Black
Sale
$82.95
$89.95 8% off
Timberland Naples Trail Chelsea Boot (Men's)
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Sale
Timberland Naples Trail Chelsea Boot(Men's) -Dark Brown Suede
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Timberland Naples Trail Chelsea Boot(Men's) -Dark Grey Suede
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$84.95 - $94.95
$130.00 up to 35% off
Crevo Blake Chelsea Boot (Men's)
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Sale
Crevo Blake Chelsea Boot(Men's) -Grey Suede
Crevo Blake Chelsea Boot(Men's) -Tan Suede
$89.95
Sudini Footwear Beatrice Ankle Bootie (Women's)
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Sale
Sudini Footwear Beatrice Ankle Bootie(Women's) -Black Kid Suede
Sale
Sudini Footwear Beatrice Ankle Bootie(Women's) -Cognac Kid Suede
Sale
$72.95
$160.00 54% off
Timberland Somers Falls Chelsea Boot (Women's)
New!
Sale
Timberland Somers Falls Chelsea Boot(Women's) -Black Full Grain Leather
Sale
$89.99
$150.00 40% off
Reef Voyage LE Chelsea Boot (Women's)
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Sale
Reef Voyage LE Chelsea Boot(Women's) -Saddle Leather
Sale
$54.95 - $69.95
$145.00 up to 52% off
Carhartt CWS4160 4
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Sale
Carhartt CWS4160 4
Sale
$96.95
$129.99 25% off
Sudini Footwear Kasha Chelsea Boot (Women's)
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Sale
Sudini Footwear Kasha Chelsea Boot(Women's) -Army Green Kid Suede
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Sudini Footwear Kasha Chelsea Boot(Women's) -Black Kid Suede
Sale
$72.95
$160.00 54% off
Ann Creek Kriel Rhinestone Chelsea Boot (Women's)
New!
Sale
Ann Creek Kriel Rhinestone Chelsea Boot(Women's) -Black Faux Suede
New
Ann Creek Kriel Rhinestone Chelsea Boot(Women's) -Burgundy Faux Suede
New
Ann Creek Kriel Rhinestone Chelsea Boot(Women's) -Navy Faux Suede
New
$67.95
UGG Hillhurst Chelsea Boot (Women's)
New!
Sale
UGG Hillhurst Chelsea Boot(Women's) -Black Suede
Sale
$71.95
$150.00 52% off
Timberland Londyn Chelsea Sneaker Boot (Women's)
New!
Sale
Timberland Londyn Chelsea Sneaker Boot(Women's) -Black Nubuck/Metallic
Sale
Timberland Londyn Chelsea Sneaker Boot(Women's) -Covert Green Nubuck
Timberland Londyn Chelsea Sneaker Boot(Women's) -White Nubuck
Sale
$69.95 - $99.95
$100.00 - $110.00 up to 36% off
UGG Camino Chelsea Boot (Men's)
New!
Sale
UGG Camino Chelsea Boot(Men's) -Taupe Suede/Nubuck
Sale
$67.95 - $139.95
$140.00 up to 51% off
GBX Panther Chelsea Boot (Men's)
New!
Sale
GBX Panther Chelsea Boot(Men's) -Black Leather
GBX Panther Chelsea Boot(Men's) -Tan Leather
$78.95
Dr. Martens Flora Chelsea Boot (Women's)
New!
Sale
Dr. Martens Flora Chelsea Boot(Women's) -Black Polished Smooth
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Dr. Martens Flora Chelsea Boot(Women's) -Black Velvet
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Dr. Martens Flora Chelsea Boot(Women's) -Cherry Red Arcadia
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Dr. Martens Flora Chelsea Boot(Women's) -Cherry Red Velvet
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$39.95 - $139.95
$130.00 - $145.00 up to 46% off
TOMS Esme Bootie (Women's)
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Sale
TOMS Esme Bootie(Women's) -Black Suede
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TOMS Esme Bootie(Women's) -Burnt Henna Leather
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TOMS Esme Bootie(Women's) -Forged Iron Grey Suede
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TOMS Esme Bootie(Women's) -Tarmac Olive Suede
Sale
$64.95 - $76.95
$129.95 - $139.95 up to 45% off
TOMS Ella Bootie (Women's)
New!
Sale
TOMS Ella Bootie(Women's) -Honey Leather/Faux Shearling
Sale
$34.95 - $66.95
$99.95 - $129.00 up to 48% off