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Discount Mens Chukka Boots

1-36 of 48 results
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Clarks Desert Boot (Men's)
Clarks Desert Boot (Men's)
New!
Sale
Clarks Desert Boot(
                                      Men's) -
                                     Black Suede
Sale
$109.95 - $399.95
$130.00 - $400.00 up to 15% off
Clarks Bushacre 2 Boot (Men's)
Clarks Bushacre 2 Boot (Men's)
Clarks Bushacre 2 Boot (Men's)
Clarks Bushacre 2 Boot (Men's)
Clarks Bushacre 2 Boot (Men's)
Clarks Bushacre 2 Boot (Men's)
New!
Sale
Clarks Bushacre 2 Boot(
                                      Men's) -
                                     Beeswax Leather
Sale
Clarks Bushacre 2 Boot(
                                      Men's) -
                                     Black Suede
Sale
Clarks Bushacre 2 Boot(
                                      Men's) -
                                     Brown Suede
Sale
Clarks Bushacre 2 Boot(
                                      Men's) -
                                     Dark Brown Leather
Sale
Clarks Bushacre 2 Boot(
                                      Men's) -
                                     Sand Suede
Sale
$84.95
$99.00 14% off
ECCO Turn GORE-TEX Boot (Men's)
ECCO Turn GORE-TEX Boot (Men's)
ECCO Turn GORE-TEX Boot (Men's)
New!
Sale
ECCO Turn GORE-TEX Boot(
                                      Men's) -
                                     Black Oil Nubuck
Sale
ECCO Turn GORE-TEX Boot(
                                      Men's) -
                                     Mocha Oil Nubuck
Sale
$174.95 - $229.95
$230.00 up to 24% off
Red Wing Handsewn Chukka (Men's)
Red Wing Handsewn Chukka (Men's)
Red Wing Handsewn Chukka (Men's)
New!
Sale
Red Wing Handsewn Chukka(
                                      Men's) -
                                     Amber Harness Leather
Sale
Red Wing Handsewn Chukka(
                                      Men's) -
                                     Charcoal Rough And Tough
Sale
$108.95 - $155.95
$310.00 up to 65% off
Rockport Charson Lace Up Ankle Boot (Men's)
Rockport Charson Lace Up Ankle Boot (Men's)
New!
Sale
Rockport Charson Lace Up Ankle Boot(
                                      Men's) -
                                     Dark Brown Leather
Sale
$109.95 - $139.95
$140.00 up to 21% off
Rockport Rugged Bucks Waterproof Boot (Men's)
Rockport Rugged Bucks Waterproof Boot (Men's)
Rockport Rugged Bucks Waterproof Boot (Men's)
Rockport Rugged Bucks Waterproof Boot (Men's)
New!
Sale
Rockport Rugged Bucks Waterproof Boot(
                                      Men's) -
                                     Espresso Nubuck
Sale
Rockport Rugged Bucks Waterproof Boot(
                                      Men's) -
                                     Tan Full Grain Leather
Sale
Rockport Rugged Bucks Waterproof Boot(
                                      Men's) -
                                     Wheat Nubuck
Sale
$109.95
$120.00 8% off
Rockport RocSports Lite 2 Chukka Boot (Men's)
Rockport RocSports Lite 2 Chukka Boot (Men's)
Rockport RocSports Lite 2 Chukka Boot (Men's)
New!
Sale
Rockport RocSports Lite 2 Chukka Boot(
                                      Men's) -
                                     Brown Leather
Sale
Rockport RocSports Lite 2 Chukka Boot(
                                      Men's) -
                                     Taupe Nubuck
Sale
$109.95
$120.00 8% off
Boston Boot Co. Commonwealth Boot (Men's)
Boston Boot Co. Commonwealth Boot (Men's)
Boston Boot Co. Commonwealth Boot (Men's)
Boston Boot Co. Commonwealth Boot (Men's)
New!
Sale
Boston Boot Co. Commonwealth Boot(
                                      Men's) -
                                     Black Leather
Sale
Boston Boot Co. Commonwealth Boot(
                                      Men's) -
                                     Brown/Nicotine Leather
Sale
Boston Boot Co. Commonwealth Boot(
                                      Men's) -
                                     Natural/White Leather
Sale
$165.95
$207.00 20% off
Clarks Stinson Hi (Men's)
Clarks Stinson Hi (Men's)
New!
Sale
Clarks Stinson Hi(
                                      Men's) -
                                     Wheat Suede
Sale
$89.95 - $99.95
$100.00 up to 10% off
Clarks Bushacre 2 (Men's)
Clarks Bushacre 2 (Men's)
Clarks Bushacre 2 (Men's)
Clarks Bushacre 2 (Men's)
New!
Sale
Clarks Bushacre 2(
                                      Men's) -
                                     Black Leather
Sale
Clarks Bushacre 2(
                                      Men's) -
                                     Navy Leather
Sale
Clarks Bushacre 2(
                                      Men's) -
                                     Tan Leather
Sale
$89.95
$100.00 10% off
Boston Boot Co. Cambridge Chukka Boot (Men's)
Boston Boot Co. Cambridge Chukka Boot (Men's)
Boston Boot Co. Cambridge Chukka Boot (Men's)
Boston Boot Co. Cambridge Chukka Boot (Men's)
New!
Sale
Boston Boot Co. Cambridge Chukka Boot(
                                      Men's) -
                                     Brown Canvas
Sale
Boston Boot Co. Cambridge Chukka Boot(
                                      Men's) -
                                     Brown Leather
Sale
Boston Boot Co. Cambridge Chukka Boot(
                                      Men's) -
                                     Natural Canvas
Sale
$157.95
$197.00 20% off
Johnston & Murphy McGuffey Chukka (Men's)
Johnston & Murphy McGuffey Chukka (Men's)
Johnston & Murphy McGuffey Chukka (Men's)
Johnston & Murphy McGuffey Chukka (Men's)
Johnston & Murphy McGuffey Chukka (Men's)
Johnston & Murphy McGuffey Chukka (Men's)
New!
Sale
Johnston & Murphy McGuffey Chukka(
                                      Men's) -
                                     Chocolate Suede
Sale
Johnston & Murphy McGuffey Chukka(
                                      Men's) -
                                     Gray Suede
Sale
Johnston & Murphy McGuffey Chukka(
                                      Men's) -
                                     Navy Suede
Sale
Johnston & Murphy McGuffey Chukka(
                                      Men's) -
                                     Olive Suede
Sale
Johnston & Murphy McGuffey Chukka(
                                      Men's) -
                                     Taupe Suede
Sale
$104.95
$125.00 16% off
Timberland Premium Chukka (Men's)
Timberland Premium Chukka (Men's)
New!
Sale
Timberland Premium Chukka(
                                      Men's) -
                                     Wheat Nubuck
Sale
$134.95
$145.00 7% off
Nunn Bush Woodbury (Men's)
Nunn Bush Woodbury (Men's)
Nunn Bush Woodbury (Men's)
Nunn Bush Woodbury (Men's)
New!
Sale
Nunn Bush Woodbury(
                                      Men's) -
                                     Brown Smooth Leather
Sale
Nunn Bush Woodbury(
                                      Men's) -
                                     Brown Suede
Sale
Nunn Bush Woodbury(
                                      Men's) -
                                     Sand Suede
Sale
$68.00
$75.00 9% off
Timberland Classic TBLŪ Chukka (Men's)
Timberland Classic TBLŪ Chukka (Men's)
New!
Sale
Timberland Classic TBLŪ Chukka(
                                      Men's) -
                                     Black Smooth Leather
Sale
$119.95 - $134.95
$135.00 up to 11% off
Boston Boot Co. Newbury Chukka Boot (Men's)
Boston Boot Co. Newbury Chukka Boot (Men's)
Boston Boot Co. Newbury Chukka Boot (Men's)
New!
Sale
Boston Boot Co. Newbury Chukka Boot(
                                      Men's) -
                                     Black Leather
Sale
Boston Boot Co. Newbury Chukka Boot(
                                      Men's) -
                                     Natural Leather
Sale
$173.95
$217.00 20% off
Tommy Hilfiger Sten Chukka (Men's)
Tommy Hilfiger Sten Chukka (Men's)
Tommy Hilfiger Sten Chukka (Men's)
New!
Sale
Tommy Hilfiger Sten Chukka(
                                      Men's) -
                                     Navy Suede/Coffee Bean Pu
Sale
Tommy Hilfiger Sten Chukka(
                                      Men's) -
                                     Taupe Suede/Coffee Bean Pu
Sale
$99.99
$130.00 23% off
Mark Nason Skechers Burwood Boot (Men's)
Mark Nason Skechers Burwood Boot (Men's)
New!
Sale
Mark Nason Skechers Burwood Boot(
                                      Men's) -
                                     Desert
Sale
$99.95
$135.00 26% off
UGG Kaldwell (Men's)
UGG Kaldwell (Men's)
New!
Sale
UGG Kaldwell(
                                      Men's) -
                                     Metal Nubuck
Sale
$99.95
$139.95 29% off
Born Asten (Men's)
Born Asten (Men's)
Born Asten (Men's)
New!
Sale
Born Asten(
                                      Men's) -
                                     Bark Leather
Sale
Born Asten(
                                      Men's) -
                                     Sabbia Suede
Sale
$94.95 - $99.95
$105.00 - $115.00 up to 13% off
Mark Nason Skechers Elmwood (Men's)
Mark Nason Skechers Elmwood (Men's)
New!
Sale
Mark Nason Skechers Elmwood(
                                      Men's) -
                                     Black
Sale
$99.95
$124.00 19% off
Frye Oliver Chukka (Men's)
Frye Oliver Chukka (Men's)
New!
Sale
Frye Oliver Chukka(
                                      Men's) -
                                     Dark Brown Leather
Sale
$139.95
$278.00 50% off
Andrew Marc Dorchester Chukka (Men's)
Andrew Marc Dorchester Chukka (Men's)
Andrew Marc Dorchester Chukka (Men's)
Andrew Marc Dorchester Chukka (Men's)
New!
Sale
Andrew Marc Dorchester Chukka(
                                      Men's) -
                                     Caribou/Black/Dark Natural/Natural Suede
Sale
Andrew Marc Dorchester Chukka(
                                      Men's) -
                                     Dark Brown/Black/Dark Natural/Natural Suede
Sale
Andrew Marc Dorchester Chukka(
                                      Men's) -
                                     Tobacco/Black/Deep Natural Suede
Sale
$133.50 - $164.95
$177.99 - $178.00 up to 25% off
Clarks Stinson Lo (Men's)
Clarks Stinson Lo (Men's)
New!
Sale
Clarks Stinson Lo(
                                      Men's) -
                                     Beeswax Leather
Sale
$89.95 - $99.95
$100.00 up to 10% off
Dockers Tussock (Men's)
Dockers Tussock (Men's)
Dockers Tussock (Men's)
New!
Sale
Dockers Tussock(
                                      Men's) -
                                     Dark Tan Burnished Crazyhorse
Sale
Dockers Tussock(
                                      Men's) -
                                     Red Brown Oiled Pull-Up Leather
Sale
$74.99 - $94.95
$90.00 up to 17% off
The North Face Ballard II Chukka Boot (Men's)
The North Face Ballard II Chukka Boot (Men's)
New!
Sale
The North Face Ballard II Chukka Boot(
                                      Men's) -
                                     Chutney Brown/Cherry Stain Brown
Sale
$103.95
$130.00 20% off
Camper Morrys Chukka Boot (Men's)
Camper Morrys Chukka Boot (Men's)
Camper Morrys Chukka Boot (Men's)
New!
Sale
Camper Morrys Chukka Boot(
                                      Men's) -
                                     Dark Green Nubuck
Sale
Camper Morrys Chukka Boot(
                                      Men's) -
                                     Medium Brown Leather
Sale
$159.99
$199.00 20% off
Marc New York by Andrew Marc Stanton (Men's)
Marc New York by Andrew Marc Stanton (Men's)
Marc New York by Andrew Marc Stanton (Men's)
New!
Sale
Marc New York by Andrew Marc Stanton(
                                      Men's) -
                                     Khaki/Antelope/Gum Canvas
Sale
Marc New York by Andrew Marc Stanton(
                                      Men's) -
                                     Olive/Catfish/Nude/Gum Canvas
Sale
$87.45 - $87.95
$128.00 up to 32% off
Lugz Pathway (Men's)
Lugz Pathway (Men's)
New!
Sale
Lugz Pathway(
                                      Men's) -
                                     Black
Sale
$54.95 - $59.95
$59.99 - $60.00 up to 8% off
Cole Haan ZeroGrand Sport Chukka Boot (Men's)
Cole Haan ZeroGrand Sport Chukka Boot (Men's)
New!
Sale
Cole Haan ZeroGrand Sport Chukka Boot(
                                      Men's) -
                                     Black
Sale
$199.95
$278.00 28% off
Burnetie Harvard (Men's)
Burnetie Harvard (Men's)
New!
Sale
Burnetie Harvard(
                                      Men's) -
                                     Black
Sale
$48.95
$70.00 30% off
Steve Madden Disick (Men's)
Steve Madden Disick (Men's)
Steve Madden Disick (Men's)
New!
Sale
Steve Madden Disick(
                                      Men's) -
                                     Black Leather
Sale
Steve Madden Disick(
                                      Men's) -
                                     Brown Leather
Sale
$99.99
$125.00 20% off
Florsheim Hifi Moc Boot (Men's)
Florsheim Hifi Moc Boot (Men's)
New!
Sale
Florsheim Hifi Moc Boot(
                                      Men's) -
                                     Mushroom Suede
Sale
$97.95 - $109.95
$110.00 up to 11% off
Steve Madden Boro (Men's)
Steve Madden Boro (Men's)
New!
Sale
Steve Madden Boro(
                                      Men's) -
                                     Black Leather
Sale
$99.99
$130.00 23% off
Steve Madden Kiero (Men's)
Steve Madden Kiero (Men's)
Steve Madden Kiero (Men's)
New!
Sale
Steve Madden Kiero(
                                      Men's) -
                                     Black Multi
Sale
Steve Madden Kiero(
                                      Men's) -
                                     Cognac Multi
Sale
$89.99
$115.00 22% off
Steve Madden Garisonn (Men's)
Steve Madden Garisonn (Men's)
Steve Madden Garisonn (Men's)
New!
Sale
Steve Madden Garisonn(
                                      Men's) -
                                     Black Leather
Sale
Steve Madden Garisonn(
                                      Men's) -
                                     Tan Leather
Sale
$89.99
$115.00 22% off