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Discount Casual Chukka Boots

Clarks Bushacre 2 Boot (Men's)
New!
Sale
Clarks Bushacre 2 Boot(Men's) -Beeswax Leather
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Clarks Bushacre 2 Boot(Men's) -Black Suede
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Clarks Bushacre 2 Boot(Men's) -Black Waxy Leather
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Clarks Bushacre 2 Boot(Men's) -Dark Brown Leather
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Clarks Bushacre 2 Boot(Men's) -Dark Olive Leather
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Clarks Bushacre 2 Boot(Men's) -Dark Tan Leather
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Clarks Bushacre 2 Boot(Men's) -Grey Leather
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Clarks Bushacre 2 Boot(Men's) -Navy Leather
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Clarks Bushacre 2 Boot(Men's) -Wheat Suede
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Clarks Bushacre 2 Boot(Men's) -Wine Leather
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$59.95 - $65.95
$100.00 up to 40% off
Timberland Classic TBLŽ Chukka (Men's)
New!
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Timberland Classic TBLŽ Chukka(Men's) -Wheat Nubuck Leather
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Timberland Classic TBLŽ Chukka(Men's) -Black Smooth Leather
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$99.95
$135.00 26% off
Clarks Desert Boot (Men's)
New!
Sale
Clarks Desert Boot(Men's) -Beeswax Full Grain Leather
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Clarks Desert Boot(Men's) -Black/Black Suede
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Clarks Desert Boot(Men's) -Blue/Grey Suede
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Clarks Desert Boot(Men's) -Bordeaux Suede
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Clarks Desert Boot(Men's) -Brown/Brown Suede
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Clarks Desert Boot(Men's) -Mahogany Suede
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Clarks Desert Boot(Men's) -Navy Canvas
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Clarks Desert Boot(Men's) -Oak Suede
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Clarks Desert Boot(Men's) -Olive/Olive Suede
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Clarks Desert Boot(Men's) -Taupe Canvas
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$98.99 - $130.00
$130.00 - $140.00 up to 29% off
Clarks Stinson Hi Moc Toe Boot (Men's)
New!
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Clarks Stinson Hi Moc Toe Boot(Men's) -Beeswax Leather
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Clarks Stinson Hi Moc Toe Boot(Men's) -Black Oily Leather
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Clarks Stinson Hi Moc Toe Boot(Men's) -Black Suede
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Clarks Stinson Hi Moc Toe Boot(Men's) -Brown Oily Leather
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Clarks Stinson Hi Moc Toe Boot(Men's) -Dark Olive Leather
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Clarks Stinson Hi Moc Toe Boot(Men's) -Sand Suede
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$89.99
$100.00 - $110.00 up to 18% off
Twisted X Boots WDM0081 Driving Moc Chukka Boot (Women's)
New!
Sale
Twisted X Boots WDM0081 Driving Moc Chukka Boot(Women's) -Brown/Tooled Flowers Leather
Sale
$99.95
$134.99 26% off
Cole Haan Original Grand Chukka Boot (Men's)
New!
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Cole Haan Original Grand Chukka Boot(Men's) -Black Leather/Black
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Cole Haan Original Grand Chukka Boot(Men's) -Woodbury Leather/Dark Roast
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$149.99 - $179.95
$180.00 up to 17% off
Twisted X Boots MDM0059 Driving Mocs Chukka Boot (Men's)
New!
Sale
Twisted X Boots MDM0059 Driving Mocs Chukka Boot(Men's) -Brown/Brown Print Leather
Sale
$79.95
$114.99 30% off
Rockport Essential Details Waterproof Chukka Boot (Men's)
New!
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Rockport Essential Details Waterproof Chukka Boot(Men's) -Black Full Grain Leather
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$109.95
$125.00 12% off
Rockport Marshall Chukka Boot (Men's)
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Rockport Marshall Chukka Boot(Men's) -Cognac Leather
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$89.45 - $119.95
$120.00 up to 25% off
Nunn Bush Lancaster Chukka Boot (Men's)
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Nunn Bush Lancaster Chukka Boot(Men's) -Black Oiled Leather
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Nunn Bush Lancaster Chukka Boot(Men's) -Brown Oiled Leather
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Nunn Bush Lancaster Chukka Boot(Men's) -Camel Suede
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$63.95
$80.00 20% off
Rockport Charson Lace Up Ankle Boot (Men's)
New!
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Rockport Charson Lace Up Ankle Boot(Men's) -Black Leather
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Rockport Charson Lace Up Ankle Boot(Men's) -Dark Brown Leather
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$99.95
$140.00 29% off
Timberland Logan Bay Plain Toe Chukka Boot (Men's)
New!
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Timberland Logan Bay Plain Toe Chukka Boot(Men's) -Black Full Grain Leather
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Timberland Logan Bay Plain Toe Chukka Boot(Men's) -Medium Brown Full Grain Leather
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$99.95
$130.00 23% off
Clarks Stinson Lo (Men's)
New!
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Clarks Stinson Lo(Men's) -Beeswax Leather
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Clarks Stinson Lo(Men's) -Black Leather
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$89.99
$100.00 10% off
White Mountain Auburn Chukka Boot (Women's)
New!
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White Mountain Auburn Chukka Boot(Women's) -Black Suede
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White Mountain Auburn Chukka Boot(Women's) -Hazel Suede
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White Mountain Auburn Chukka Boot(Women's) -Navy Suede
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White Mountain Auburn Chukka Boot(Women's) -Taupe Suede
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$49.99
$89.00 44% off
Naot Levanto Lace Up Ankle Boot (Women's)
New!
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Naot Levanto Lace Up Ankle Boot(Women's) -Desert Suede
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$202.99 - $224.95
$225.00 up to 10% off
New Balance 3020v1 Chukka Boot (Men's)
New!
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New Balance 3020v1 Chukka Boot(Men's) -Bitter Chocolate/Brindle
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New Balance 3020v1 Chukka Boot(Men's) -Black/Black
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$134.95
$159.95 16% off
Superfeet Olympia Chukka Boot (Women's)
New!
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Superfeet Olympia Chukka Boot(Women's) -Black Iris/Turtledove
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Superfeet Olympia Chukka Boot(Women's) -Black/Turtledove
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$91.45
$130.00 30% off
Clarks Wallabee (Men's)
New!
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Clarks Wallabee(Men's) -Black/Black Leather
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$140.00
$140.00 - $160.00 up to 12% off
Ariat Spitfire Chukka Boot (Men's)
New!
Sale
Ariat Spitfire Chukka Boot(Men's) -Brown Bomber Full Grain Leather
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$99.95 - $109.95
$99.95 - $109.95 up to 9% off
Ariat Cruiser Lace Chukka Boot (Women's)
New!
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Ariat Cruiser Lace Chukka Boot(Women's) -Dirty Taupe Suede
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$79.95 - $94.95
$89.95 - $94.95 up to 11% off
Clarks Tilden Top Chukka Boot (Men's)
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Clarks Tilden Top Chukka Boot(Men's) -Black Full Grain Leather
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$102.99
$115.00 10% off
Wolverine Bedford Soft Toe Chukka Boot (Men's)
New!
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Wolverine Bedford Soft Toe Chukka Boot(Men's) -Black Full Grain Leather
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Wolverine Bedford Soft Toe Chukka Boot(Men's) -Brown Full Grain Leather
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$88.95
$115.00 23% off
Clarks Desert Boot (Women's)
New!
Sale
Clarks Desert Boot(Women's) -Beeswax Leather
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Clarks Desert Boot(Women's) -Beeswax/Beeswax Leather
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Clarks Desert Boot(Women's) -Bordeaux Suede
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Clarks Desert Boot(Women's) -Chocolate Suede
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Clarks Desert Boot(Women's) -Ink Suede
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Clarks Desert Boot(Women's) -Oak Suede
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Clarks Desert Boot(Women's) -Oakwood Suede
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Clarks Desert Boot(Women's) -Olive Suede
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Clarks Desert Boot(Women's) -Taupe Distressed
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$96.99 - $130.00
$120.00 - $140.00 up to 19% off
Timberland Premium Chukka (Men's)
New!
Sale
Timberland Premium Chukka(Men's) -Wheat Nubuck
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$89.99
$145.00 38% off
Timberland Groveton Leather/Fabric Chukka (Men's)
New!
Sale
Timberland Groveton Leather/Fabric Chukka(Men's) -Black Nubuck/Textile
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$55.99
$80.00 30% off
Clarks Cotrell Top Chukka Boot (Men's)
New!
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Clarks Cotrell Top Chukka Boot(Men's) -Black Oily Full Grain Leather
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Clarks Cotrell Top Chukka Boot(Men's) -Tobacco Full Grain Leather
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$98.99
$110.00 10% off
Clarks Atticus Limit Chukka Boot (Men's)
New!
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Clarks Atticus Limit Chukka Boot(Men's) -Navy Nubuck
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Clarks Atticus Limit Chukka Boot(Men's) -Taupe Nubuck
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$94.45 - $135.00
$135.00 up to 30% off
Timberland Killington Chukka Boot (Men's)
New!
Sale
Timberland Killington Chukka Boot(Men's) -Black Leather
Sale
$79.95
$125.00 36% off
Ariat Edge LTE Moc Composite Toe Chukka Boot (Men's)
New!
Sale
Ariat Edge LTE Moc Composite Toe Chukka Boot(Men's) -Dark Brown Leather
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$119.95
$129.95 8% off
Rockport Rydley Chukka Boot (Men's)
New!
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Rockport Rydley Chukka Boot(Men's) -Dark Bitter Chocolate Nubuck
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Rockport Rydley Chukka Boot(Men's) -Taupe Nubuck
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$97.99 - $114.95
$115.00 up to 15% off
Wolverine Bedford Steel Toe Chukka Boot (Men's)
New!
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Wolverine Bedford Steel Toe Chukka Boot(Men's) -Black Full Grain Leather
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Wolverine Bedford Steel Toe Chukka Boot(Men's) -Brown Full Grain Leather
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$76.95 - $92.95
$120.00 up to 36% off
Twisted X Boots MDM0061 Driving Mocs Chukka Boot (Men's)
New!
Sale
Twisted X Boots MDM0061 Driving Mocs Chukka Boot(Men's) -Tan/Tooled Flowers Leather
Sale
$103.95
$139.99 26% off
Lugz Mantle Mid Chukka Work Boot (Men's)
New!
Sale
Lugz Mantle Mid Chukka Work Boot(Men's) -Black Synthetic
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Lugz Mantle Mid Chukka Work Boot(Men's) -Golden Wheat/Tan-Khaki/Gum Synthetic
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$43.99
$54.99 20% off
Ariat Edge LTE Moc H2O Composite Toe Chukka Boot (Men's)
New!
Sale
Ariat Edge LTE Moc H2O Composite Toe Chukka Boot(Men's) -Dark Brown Leather
Sale
$139.95
$149.95 7% off
Cole Haan Wagner Grand Apron Chukka Boot (Men's)
New!
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Cole Haan Wagner Grand Apron Chukka Boot(Men's) -Black Waterproof Leather
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Cole Haan Wagner Grand Apron Chukka Boot(Men's) -Java Nubuck Waterproof Leather
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Cole Haan Wagner Grand Apron Chukka Boot(Men's) -Mesquite Waterproof Leather
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$239.99
$280.00 14% off
Stacy Adams Beckett Cap Toe Chukka Boot 24984 (Men's)
New!
Sale
Stacy Adams Beckett Cap Toe Chukka Boot 24984(Men's) -Brown Leather
Sale
$84.95
$105.00 19% off