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Flat Heel Chukka Boots

Timberland Davis Square Fabric/Leather Chukka Boot (Men's)
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Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Black Nubuck/Cordura® EcoMade Fiber
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Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Medium Grey Nubuck/Cordura® Fiber
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Timberland Davis Square Fabric/Leather Chukka Boot(Men's) -Navy Nubuck/Cordura® Fiber
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$54.95
$80.00 31% off
Twisted X Boots MDM0014 (Men's)
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Twisted X Boots MDM0014(Men's) -Copper Leather
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$83.95
$109.99 24% off
Nunn Bush Galloway Chukka Boot (Men's)
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Nunn Bush Galloway Chukka Boot(Men's) -Beige Suede
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Nunn Bush Galloway Chukka Boot(Men's) -Dark Brown Suede
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$59.95
$80.00 25% off
White Mountain Auburn Chukka Boot (Women's)
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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) -Taupe Suede
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$49.99
$89.00 44% off
Keen Grayson Chukka Boot (Men's)
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Keen Grayson Chukka Boot(Men's) -Mid Brown/Scylum
Keen Grayson Chukka Boot(Men's) -Sage/Lama
$129.95
Timberland FlyRoam Go Lace Chukka Boot (Women's)
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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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$94.99
$120.00 21% off
Nunn Bush Ozark Plain Toe Chukka Boot (Men's)
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Nunn Bush Ozark Plain Toe Chukka Boot(Men's) -Black Tumble Leather
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Nunn Bush Ozark Plain Toe Chukka Boot(Men's) -Brown Chamois Leather
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Nunn Bush Ozark Plain Toe Chukka Boot(Men's) -Rust Leather
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Nunn Bush Ozark Plain Toe Chukka Boot(Men's) -Tan Chamois Leather
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$70.95
$95.00 25% off
Crevo Alameda Chukka Boot (Men's)
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Crevo Alameda Chukka Boot(Men's) -Chestnut Leather
Crevo Alameda Chukka Boot(Men's) -Gray Suede
$79.95
Nunn Bush Middleton Plain Toe Chukka Boot (Men's)
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Nunn Bush Middleton Plain Toe Chukka Boot(Men's) -Black Leather
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Nunn Bush Middleton Plain Toe Chukka Boot(Men's) -Brown Leather
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Nunn Bush Middleton Plain Toe Chukka Boot(Men's) -Cognac Leather
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$70.95
$95.00 25% off
Eastland Seneca (Women's)
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Eastland Seneca(Women's) -Khaki Suede
Eastland Seneca(Women's) -Natural Leather
Eastland Seneca(Women's) -Tan Waxee Leather
$99.95
Nunn Bush Nantucket Cap Toe Chukka Boot (Men's)
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Nunn Bush Nantucket Cap Toe Chukka Boot(Men's) -Black Leather
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$67.95
$90.00 24% off
ECCO Crepetray Chukka Boot (Men's)
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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
Umi Jared Chukka (Boys')
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Umi Jared Chukka(Boys') -Black Leather
$64.95
Umi Jared II Chukka (Boys')
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Umi Jared II Chukka(Boys') -Black Leather
Umi Jared II Chukka(Boys') -Cognac Leather
$69.95
Nunn Bush Littleton Plain Toe Chukka Boot (Men's)
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Nunn Bush Littleton Plain Toe Chukka Boot(Men's) -Brown Leather
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Nunn Bush Littleton Plain Toe Chukka Boot(Men's) -Tan Leather
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$67.95
$90.00 24% off
Sperry Top-Sider Bahama Lug Naval Ankle Boot (Men's)
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Sperry Top-Sider Bahama Lug Naval Ankle Boot(Men's) -Black Canvas
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$39.97
$69.95 43% off
Nunn Bush Memphis St. Moc Toe Waterproof Boot (Men's)
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Nunn Bush Memphis St. Moc Toe Waterproof Boot(Men's) -Black Smooth Leather
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$70.95
$95.00 25% off
Nunn Bush Sal Chukka Boot (Men's)
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Nunn Bush Sal Chukka Boot(Men's) -Black Synthetic
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Nunn Bush Sal Chukka Boot(Men's) -Brown Synthetic
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$52.95
$70.00 24% off
Nunn Bush Nantucket Plain Toe Chukka Boot (Men's)
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Nunn Bush Nantucket Plain Toe Chukka Boot(Men's) -Black Leather
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$67.95
$90.00 24% off
ROBERT WAYNE Greyson Suede Chukka Boot (Men's)
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ROBERT WAYNE Greyson Suede Chukka Boot(Men's) -Cognac Suede
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$47.95
$140.00 66% off
ECCO Crepetray Chukka Boot (Women's)
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ECCO Crepetray Chukka Boot(Women's) -Amber Nubuck Leather
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ECCO Crepetray Chukka Boot(Women's) -White/Powder Full Grain Leather
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$94.95 - $118.95
$160.00 - $170.00 up to 41% off