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Discount Mens Chukka Boots

1-36 of 72 results
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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
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 - $99.95
$100.00 up to 10% 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
Woolrich Lane (Men's)
Woolrich Lane (Men's)
Woolrich Lane (Men's)
Woolrich Lane (Men's)
New!
Sale
Woolrich Lane(
Men's) -
Ballentyne
Sale
Woolrich Lane(
Men's) -
Camel
Sale
Woolrich Lane(
Men's) -
Yellowstone
Sale
$80.95
$160.00 49% 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
Dr. Martens Barnie Chukka Boot (Men's)
Dr. Martens Barnie Chukka Boot (Men's)
Dr. Martens Barnie Chukka Boot (Men's)
New!
Sale
Dr. Martens Barnie Chukka Boot(
Men's) -
Black Grizzly
Sale
Dr. Martens Barnie Chukka Boot(
Men's) -
Dark Brown Grizzly
Sale
$89.95 - $119.95
$120.00 up to 25% off
Steve Madden Hestonn (Men's)
Steve Madden Hestonn (Men's)
Steve Madden Hestonn (Men's)
Steve Madden Hestonn (Men's)
New!
Sale
Steve Madden Hestonn(
Men's) -
Dark Brown Leather
Sale
Steve Madden Hestonn(
Men's) -
Grey Leather
Sale
Steve Madden Hestonn(
Men's) -
Tan Leather
Sale
$65.95 - $84.95
$90.00 up to 27% 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
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
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
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
Timberland Earthkeepers Brook Park Chukka (Men's)
Timberland Earthkeepers Brook Park Chukka (Men's)
New!
Sale
Timberland Earthkeepers Brook Park Chukka(
Men's) -
Red Brown Smooth
Sale
$104.95 - $129.95
$130.00 up to 19% off
Clarks Stinson Lo (Men's)
Clarks Stinson Lo (Men's)
New!
Sale
Clarks Stinson Lo(
Men's) -
Beeswax Leather
Sale
$89.95
$100.00 10% off
Nunn Bush Rawson Chukka (Men's)
Nunn Bush Rawson Chukka (Men's)
Nunn Bush Rawson Chukka (Men's)
New!
Sale
Nunn Bush Rawson Chukka(
Men's) -
Black Leather
Sale
Nunn Bush Rawson Chukka(
Men's) -
Chestnut Leather
Sale
$71.95
$90.00 20% 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
Dockers Tussock (Men's)
Dockers Tussock (Men's)
Dockers Tussock (Men's)
Dockers Tussock (Men's)
New!
Sale
Dockers Tussock(
Men's) -
Black Leather
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
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
Timberland Britton Hill Waterproof Chukka Boot (Men's)
Timberland Britton Hill Waterproof Chukka Boot (Men's)
Timberland Britton Hill Waterproof Chukka Boot (Men's)
New!
Sale
Timberland Britton Hill Waterproof Chukka Boot(
Men's) -
Black Quartz with Buttersoft
Sale
Timberland Britton Hill Waterproof Chukka Boot(
Men's) -
Chestnut Quartz with Buttersoft
Sale
$140.95
$180.00 22% 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
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
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
Crocs Thompson Desert Boot (Men's)
Crocs Thompson Desert Boot (Men's)
New!
Sale
Crocs Thompson Desert Boot(
Men's) -
Espresso/Khaki
Sale
$56.95
$74.95 24% 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
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
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
Rockport Sharp & Ready Charson Boot (Men's)
Rockport Sharp & Ready Charson Boot (Men's)
New!
Sale
Rockport Sharp & Ready Charson Boot(
Men's) -
Dark Bitter Chocolate/Brick Suede
Sale
$99.95 - $139.95
$140.00 up to 29% 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
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 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
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
$77.95 - $89.95
$90.00 up to 13% off
Lugz Chukka Ripstop (Men's)
Lugz Chukka Ripstop (Men's)
New!
Sale
Lugz Chukka Ripstop(
Men's) -
Black Ripstop Nylon
Sale
$39.95
$64.99 39% 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
Dr. Martens Giggs 4 Eye Chukka Boot (Men's)
Dr. Martens Giggs 4 Eye Chukka Boot (Men's)
New!
Sale
Dr. Martens Giggs 4 Eye Chukka Boot(
Men's) -
Tan Plus
Sale
$79.95
$105.00 24% off
Marc New York by Andrew Marc Walden Chukka (Men's)
Marc New York by Andrew Marc Walden Chukka (Men's)
Marc New York by Andrew Marc Walden Chukka (Men's)
Marc New York by Andrew Marc Walden Chukka (Men's)
New!
Sale
Marc New York by Andrew Marc Walden Chukka(
Men's) -
Black Leather
Sale
Marc New York by Andrew Marc Walden Chukka(
Men's) -
Cobbie/Dark Honey Leather
Sale
Marc New York by Andrew Marc Walden Chukka(
Men's) -
Tan/Honey Leather
Sale
$69.95
$128.00 45% 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