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Discount Mens Chukka Boots

1-36 of 69 results
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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
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
$84.95
$99.00 14% 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
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
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
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 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
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
New!
Sale
Stacy Adams Astro 53404(
                                      Men's) -
                                     Black Smooth Leather
Sale
Stacy Adams Astro 53404(
                                      Men's) -
                                     Brown Suede
Sale
Stacy Adams Astro 53404(
                                      Men's) -
                                     Gray Suede
Sale
$62.95 - $89.95
$90.00 up to 30% 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
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 Darble Mid Chukka (Men's)
Clarks Darble Mid Chukka (Men's)
New!
Sale
Clarks Darble Mid Chukka(
                                      Men's) -
                                     Cognac Leather
Sale
$98.95
$150.00 34% 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
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) -
                                     Tan Leather
Sale
$81.95 - $119.95
$120.00 up to 32% 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
Clarks Fulham Hi (Men's)
Clarks Fulham Hi (Men's)
New!
Sale
Clarks Fulham Hi(
                                      Men's) -
                                     Brown Leather
Sale
$51.95
$125.00 58% 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
Clarks Hawkley Rise Chukka (Men's)
Clarks Hawkley Rise Chukka (Men's)
New!
Sale
Clarks Hawkley Rise Chukka(
                                      Men's) -
                                     Dark Brown Combi
Sale
$82.45 - $124.95
$125.00 up to 34% 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
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
$151.95
$217.00 30% 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
$144.95
$207.00 30% 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
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
$129.95
$199.00 35% off
Lugz Freeman Chukka Boot (Men's)
Lugz Freeman Chukka Boot (Men's)
Lugz Freeman Chukka Boot (Men's)
New!
Sale
Lugz Freeman Chukka Boot(
                                      Men's) -
                                     Black/Cream Perma Hide
Sale
Lugz Freeman Chukka Boot(
                                      Men's) -
                                     Seascape/Cream/Cymbal Textile
Sale
$59.95
$79.99 25% off
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
$49.95
$69.99 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
Rockport Rugged Bucks Waterproof Boot (Men's)
Rockport Rugged Bucks Waterproof Boot (Men's)
New!
Sale
Rockport Rugged Bucks Waterproof Boot(
                                      Men's) -
                                     Tan Full Grain Leather
Sale
$109.95 - $119.95
$120.00 up to 8% 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 Harman Chukka (Men's)
Marc New York by Andrew Marc Harman Chukka (Men's)
Marc New York by Andrew Marc Harman Chukka (Men's)
Marc New York by Andrew Marc Harman Chukka (Men's)
New!
Sale
Marc New York by Andrew Marc Harman Chukka(
                                      Men's) -
                                     Ash/DarkAsh/Gum Suede
Sale
Marc New York by Andrew Marc Harman Chukka(
                                      Men's) -
                                     Elm/Cymbal/Light Gum Suede/Leather
Sale
Marc New York by Andrew Marc Harman Chukka(
                                      Men's) -
                                     Mahogany/Espresso/Gum Suede/Leather
Sale
$69.95 - $79.99
$128.00 up to 45% 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
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
Rockport Total Motion Fusion Desert Boot (Men's)
Rockport Total Motion Fusion Desert Boot (Men's)
Rockport Total Motion Fusion Desert Boot (Men's)
New!
Sale
Rockport Total Motion Fusion Desert Boot(
                                      Men's) -
                                     New Dress Blues
Sale
Rockport Total Motion Fusion Desert Boot(
                                      Men's) -
                                     Rocksand
Sale
$104.95 - $149.95
$150.00 up to 30% off
Lugz Agent Chukka Boot (Men's)
Lugz Agent Chukka Boot (Men's)
New!
Sale
Lugz Agent Chukka Boot(
                                      Men's) -
                                     Black/Cymbal Perma Hide
Sale
$57.45
$69.99 18% 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
$230.00 24% 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