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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 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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$54.99 - $67.99
$100.00 up to 45% off
Steve Madden Harken Chukka Boot (Men's)
New!
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Steve Madden Harken Chukka Boot(Men's) -Black  Leather
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Steve Madden Harken Chukka Boot(Men's) -Cognac Leather
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$79.95
$90.00 11% off
Ariat Spitfire Chukka Boot (Men's)
New!
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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
Clarks Desert Boot (Women's)
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Clarks Desert Boot(Women's) -Beeswax Smooth Leather
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Clarks Desert Boot(Women's) -Black Suede
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Clarks Desert Boot(Women's) -Chocolate Suede
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Clarks Desert Boot(Women's) -Legacy Black Suede
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Clarks Desert Boot(Women's) -Taupe Distressed
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$107.99 - $130.00
$120.00 - $140.00 up to 10% off
Clarks Stinson Hi Moc Toe Boot (Men's)
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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) -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 - $98.99
$100.00 - $110.00 up to 10% off
Clarks Wallabee (Men's)
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Clarks Wallabee(Men's) -Beeswax/Beeswax Leather
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Clarks Wallabee(Men's) -Black/Black Leather
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$139.95
$135.00 - $160.00 up to 13% off
Clarks Medora Sage Chukka Boot (Women's)
New!
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Clarks Medora Sage Chukka Boot(Women's) -Black Suede/Full Grain Leather
Sale
$47.45
$120.00 60% off
Twisted X Boots MDM0059 Driving Mocs Chukka Boot (Men's)
New!
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Twisted X Boots MDM0059 Driving Mocs Chukka Boot(Men's) -Brown/Brown Print Leather
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$99.95
$114.99 13% off
Twisted X Boots WDM0081 Driving Moc Chukka Boot (Women's)
New!
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Twisted X Boots WDM0081 Driving Moc Chukka Boot(Women's) -Brown/Tooled Flowers Leather
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$124.95
$134.99 7% 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
Clarks Hinman Mid Chukka Boot (Men's)
New!
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Clarks Hinman Mid Chukka Boot(Men's) -Black Leather
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Clarks Hinman Mid Chukka Boot(Men's) -Dark Tan Suede
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Clarks Hinman Mid Chukka Boot(Men's) -Mahogany Leather
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$89.99
$100.00 10% off
Timberland Killington Chukka Boot (Men's)
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Timberland Killington Chukka Boot(Men's) -Black Leather
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$99.95
$125.00 20% off
Clarks Desert Boot (Men's)
New!
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Clarks Desert Boot(Men's) -Brown Suede
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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) -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) -Taupe Canvas
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$96.99 - $129.95
$130.00 - $140.00 up to 31% off
Twisted X Boots MDM0061 Driving Mocs Chukka Boot (Men's)
New!
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Twisted X Boots MDM0061 Driving Mocs Chukka Boot(Men's) -Tan/Tooled Flowers Leather
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$129.95
$139.99 7% off
Rockport Charson Lace Up Ankle Boot (Men's)
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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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$79.95
$140.00 43% off
Clarks Stratton Limit Boot (Men's)
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Clarks Stratton Limit Boot(Men's) -Brown Leather
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$67.97
$135.00 50% off
Florsheim Montinaro Chukka Boot (Men's)
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Florsheim Montinaro Chukka Boot(Men's) -Saddle Tan Smooth Leather
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Florsheim Montinaro Chukka Boot(Men's) -Black Smooth Leather
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$99.95
$110.00 9% off
Clarks Stinson Lo (Men's)
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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
UGG Neumel Boot (Men's)
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UGG Neumel Boot(Men's) -Redwood
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$95.95 - $149.95
$130.00 - $150.00 up to 36% off
Cole Haan GrandPro Chukka Sneaker (Men's)
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Cole Haan GrandPro Chukka Sneaker(Men's) -Black Leather
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$112.95
$150.00 25% off
Lugz Mantle Mid Chukka Work Boot (Men's)
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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
Clarks Broyd Mid Chukka Boot (Men's)
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Clarks Broyd Mid Chukka Boot(Men's) -Black Leather
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Clarks Broyd Mid Chukka Boot(Men's) -Tan Leather
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$111.45
$140.00 20% off
Stacy Adams Astro 53404 (Men's)
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Stacy Adams Astro 53404(Men's) -Black Smooth Leather
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$79.95 - $89.95
$90.00 up to 11% off
Dansko Jake Plain Toe Chukka Boot (Men's)
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Dansko Jake Plain Toe Chukka Boot(Men's) -Black Antiqued Calf
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Dansko Jake Plain Toe Chukka Boot(Men's) -Taupe Milled Nubuck
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$125.95
$194.95 35% off
Rockport Classic Break Chukka Boot (Men's)
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Rockport Classic Break Chukka Boot(Men's) -Dark Bitter Chocolate Suede
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Rockport Classic Break Chukka Boot(Men's) -Dark Brown Leather
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$106.45
$120.00 11% off
Clarks Atticus Limit Chukka Boot (Men's)
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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 - $134.95
$135.00 up to 30% off
Wolverine Bedford Soft Toe Chukka Boot (Men's)
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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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$104.99
$115.00 9% off
Clarks Desert Trek (Men's)
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Clarks Desert Trek(Men's) -Chestnut Leather
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$119.99 - $139.95
$140.00 up to 14% off
Clarks Clarkdale Bara Chukka Boot (Men's)
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Clarks Clarkdale Bara Chukka Boot(Men's) -Olive Suede
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$115.99
$170.00 32% off
ECCO Crepetray Chukka Boot (Men's)
New!
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ECCO Crepetray Chukka Boot(Men's) -Lion/Powder Cow Leather/Cow Nubuck
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$135.99
$170.00 20% off
Caterpillar Mitch Chukka Boot (Men's)
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Caterpillar Mitch Chukka Boot(Men's) -Dark Beige Leather
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$78.95
$90.00 12% off
Ariat Edge LTE Moc Composite Toe Chukka Boot (Men's)
New!
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Ariat Edge LTE Moc Composite Toe Chukka Boot(Men's) -Dark Brown Leather
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$119.95
$129.95 8% off
Timberland FlyRoam Go Lace Chukka Boot (Women's)
New!
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Timberland FlyRoam Go Lace Chukka Boot(Women's) -Jet Black Escape/Natural Sandune
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Timberland FlyRoam Go Lace Chukka Boot(Women's) -Pure Cashmere Escape/Natural Sandune
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$94.95
$120.00 21% off
Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
New!
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Stacy Adams Dabney Plain Toe Chukka Boot 24977(Men's) -Black Suede Suede
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Stacy Adams Dabney Plain Toe Chukka Boot 24977(Men's) -Chestnut Suede
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Stacy Adams Dabney Plain Toe Chukka Boot 24977(Men's) -Navy Suede
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$86.45
$100.00 14% off
Clarks Wilrose Sage Chukka Boot (Women's)
New!
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Clarks Wilrose Sage Chukka Boot(Women's) -Black Nubuck
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Clarks Wilrose Sage Chukka Boot(Women's) -Brown Nubuck
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$58.45
$130.00 55% off
TOMS Chukka Boot Leather (Men's)
New!
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TOMS Chukka Boot Leather(Men's) -Brown Waterproof Pull Up Leather
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$98.00 - $99.95
$98.00 - $139.00 up to 28% off