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Discount Mens Chukka Boots

1-36 of 62 results
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Clarks Desert Boot (Men's)
Clarks Desert Boot (Men's)
New!
Sale
Clarks Desert Boot(
                                      Men's) -
                                     Sand SixtyFive Suede
Sale
$129.95 - $180.45
$130.00 - $400.00 up to 55% 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
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
Bed Stu Draco Chukka Boot (Men's)
Bed Stu Draco Chukka Boot (Men's)
Bed Stu Draco Chukka Boot (Men's)
New!
Sale
Bed Stu Draco Chukka Boot(
                                      Men's) -
                                     Black Handwash Leather
Sale
Bed Stu Draco Chukka Boot(
                                      Men's) -
                                     Toast Zone Antiqued Leather
Sale
$109.99 - $139.95
$155.00 up to 29% 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
Clarks Garren Free Chukka Boot (Men's)
Clarks Garren Free Chukka Boot (Men's)
Clarks Garren Free Chukka Boot (Men's)
New!
Sale
Clarks Garren Free Chukka Boot(
                                      Men's) -
                                     Brown Full Grain Leather
Sale
Clarks Garren Free Chukka Boot(
                                      Men's) -
                                     Taupe Full Grain Leather
Sale
$73.95 - $82.45
$110.00 up to 33% off
Bed Stu Randall (Men's)
Bed Stu Randall (Men's)
Bed Stu Randall (Men's)
New!
Sale
Bed Stu Randall(
                                      Men's) -
                                     Black Lux Leather
Sale
Bed Stu Randall(
                                      Men's) -
                                     Tan Rustic/White Bfs
Sale
$169.99 - $197.95
$220.00 up to 23% off
Clarks Bushacre 2 (Men's)
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) -
                                     Black Perforated Full Grain Leather
Sale
Clarks Bushacre 2(
                                      Men's) -
                                     Navy Leather
Sale
Clarks Bushacre 2(
                                      Men's) -
                                     Tan Leather
Sale
$73.95 - $99.95
$100.00 up to 26% 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
Twisted X Boots MDM0020 (Men's)
Twisted X Boots MDM0020 (Men's)
New!
Sale
Twisted X Boots MDM0020(
                                      Men's) -
                                     Dusty Grey Leather
Sale
$60.49
$104.99 42% off
Bostonian Verner Style Chukka Boot (Men's)
Bostonian Verner Style Chukka Boot (Men's)
New!
Sale
Bostonian Verner Style Chukka Boot(
                                      Men's) -
                                     Navy Leather
Sale
$73.95
$100.00 26% off
ECCO Turn GORE-TEX Boot (Men's)
ECCO Turn GORE-TEX Boot (Men's)
New!
Sale
ECCO Turn GORE-TEX Boot(
                                      Men's) -
                                     Mocha Oil Nubuck
Sale
$174.95 - $229.95
$230.00 up to 24% 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
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
Lugz Chukka Ballistic (Men's)
Lugz Chukka Ballistic (Men's)
New!
Sale
Lugz Chukka Ballistic(
                                      Men's) -
                                     Wheat/Cream Ballistic Nylon
Sale
$39.95
$64.99 39% off
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) -
                                     Olive/Catfish/Nude/Gum Canvas
Sale
$59.99
$128.00 53% off
Nunn Bush Hawley Chukka Boot (Men's)
Nunn Bush Hawley Chukka Boot (Men's)
Nunn Bush Hawley Chukka Boot (Men's)
New!
Sale
Nunn Bush Hawley Chukka Boot(
                                      Men's) -
                                     Black Leather
Sale
Nunn Bush Hawley Chukka Boot(
                                      Men's) -
                                     Brown Leather
Sale
$72.00
$90.00 20% 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
$64.00 - $68.00
$80.00 - $85.00 up to 20% 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
UGG Galen Chukka Boot (Men's)
UGG Galen Chukka Boot (Men's)
UGG Galen Chukka Boot (Men's)
New!
Sale
UGG Galen Chukka Boot(
                                      Men's) -
                                     Black Leather
Sale
UGG Galen Chukka Boot(
                                      Men's) -
                                     Espresso Leather
Sale
$144.95
$195.00 26% 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
Frye Jim Chukka Boot (Men's)
Frye Jim Chukka Boot (Men's)
Frye Jim Chukka Boot (Men's)
New!
Sale
Frye Jim Chukka Boot(
                                      Men's) -
                                     Black Leather
Sale
Frye Jim Chukka Boot(
                                      Men's) -
                                     Cognac Leather
Sale
$213.95
$268.00 20% 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
$69.99
$90.00 22% off
Bed Stu Hoover Ankle Boot (Men's)
Bed Stu Hoover Ankle Boot (Men's)
New!
Sale
Bed Stu Hoover Ankle Boot(
                                      Men's) -
                                     Black Handwash Leather
Sale
$121.95
$135.00 10% off
Bed Stu Uncle Dowell (Men's)
Bed Stu Uncle Dowell (Men's)
Bed Stu Uncle Dowell (Men's)
New!
Sale
Bed Stu Uncle Dowell(
                                      Men's) -
                                     Black Dirty Veg Leather
Sale
Bed Stu Uncle Dowell(
                                      Men's) -
                                     Tan Greenland Leather
Sale
$49.99
$85.00 41% off
Deer Stags Seattle Boot (Men's)
Deer Stags Seattle Boot (Men's)
Deer Stags Seattle Boot (Men's)
New!
Sale
Deer Stags Seattle Boot(
                                      Men's) -
                                     Black
Sale
Deer Stags Seattle Boot(
                                      Men's) -
                                     Luggage
Sale
$59.99
$80.00 25% 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) -
                                     Coach/Deep Natural Leather
Sale
Andrew Marc Dorchester Chukka(
                                      Men's) -
                                     Sandstone/Deep Natural Suede
Sale
Andrew Marc Dorchester Chukka(
                                      Men's) -
                                     T.Moro/Deep Natural Leather
Sale
$109.99 - $129.99
$178.00 - $198.00 up to 38% off
Lugz Cargo Ankle Boot (Men's)
Lugz Cargo Ankle Boot (Men's)
Lugz Cargo Ankle Boot (Men's)
Lugz Cargo Ankle Boot (Men's)
New!
Sale
Lugz Cargo Ankle Boot(
                                      Men's) -
                                     Black Permahide
Sale
Lugz Cargo Ankle Boot(
                                      Men's) -
                                     Black/Charcoal Durabrush
Sale
Lugz Cargo Ankle Boot(
                                      Men's) -
                                     Golden Wheat/Cream/Bark/Gum Thermabuck
Sale
$49.95
$69.99 29% off
Twisted X Boots MDMS003 (Men's)
Twisted X Boots MDMS003 (Men's)
New!
Sale
Twisted X Boots MDMS003(
                                      Men's) -
                                     Dusty Tan Leather
Sale
$60.49
$104.99 42% off
Lugz Rickshaw (Men's)
Lugz Rickshaw (Men's)
Lugz Rickshaw (Men's)
Lugz Rickshaw (Men's)
Lugz Rickshaw (Men's)
New!
Sale
Lugz Rickshaw(
                                      Men's) -
                                     Black Permahide
Sale
Lugz Rickshaw(
                                      Men's) -
                                     Black/Gum Synthetic Suede
Sale
Lugz Rickshaw(
                                      Men's) -
                                     Dark Mahogany/Gum Permahide
Sale
Lugz Rickshaw(
                                      Men's) -
                                     Sand/Gum Synthetic Suede
Sale
$49.95
$49.95 - $69.99 up to 29% off
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
$89.00
$178.00 50% off
Tommy Hilfiger Bradley Boot (Men's)
Tommy Hilfiger Bradley Boot (Men's)
New!
Sale
Tommy Hilfiger Bradley Boot(
                                      Men's) -
                                     Coffee Bean Ultimate Leather
Sale
$55.99
$100.00 44% off
Marc New York by Andrew Marc Essex Chukka (Men's)
Marc New York by Andrew Marc Essex Chukka (Men's)
Marc New York by Andrew Marc Essex Chukka (Men's)
New!
Sale
Marc New York by Andrew Marc Essex Chukka(
                                      Men's) -
                                     Black/Cymbal Leather
Sale
Marc New York by Andrew Marc Essex Chukka(
                                      Men's) -
                                     Oxblood/Cymbal Leather
Sale
$84.99
$148.00 43% 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
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
UGG Westly (Men's)
UGG Westly (Men's)
New!
Sale
UGG Westly(
                                      Men's) -
                                     Metal
Sale
$87.95
$111.95 21% off