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    Discount Mens Chukka Boots

    1-36 of 69 results
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    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    New!
    Sale
    Clarks Wallabee Boot(
Men's) -
Brown Tumbled Leather
    Sale
    $52.95 - $199.95
    $140.00 - $200.00 up to 62% off
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(
Men's) -
Sand Somerset
    Sale
    $82.45 - $179.95
    $130.00 - $180.00 up to 37% 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
    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
    Tsubo Beale (Men's)
    Tsubo Beale (Men's)
    New!
    Sale
    Tsubo Beale(
Men's) -
Black Leather
    Sale
    $37.95
    $150.00 75% 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
    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
    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
    $89.95 - $99.95
    $100.00 up to 10% 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
    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
    Steve Madden Harken Chukka (Men's)
    Steve Madden Harken Chukka (Men's)
    New!
    Sale
    Steve Madden Harken Chukka(
Men's) -
Cognac Leather
    Sale
    $84.95 - $89.95
    $90.00 up to 6% 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
    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
    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
    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
    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
    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
    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
    $125.00 34% 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
    Timberland Earthkeepers City Lite Waterproof Chukka (Men's)
    Timberland Earthkeepers City Lite Waterproof Chukka (Men's)
    Timberland Earthkeepers City Lite Waterproof Chukka (Men's)
    New!
    Sale
    Timberland Earthkeepers City Lite Waterproof Chukka(
Men's) -
Black Smooth Leather
    Sale
    Timberland Earthkeepers City Lite Waterproof Chukka(
Men's) -
Brown Oiled Nubuck
    Sale
    $94.95
    $120.00 21% 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
    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
    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
    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
    Twisted X Boots MDMS003 (Men's)
    Twisted X Boots MDMS003 (Men's)
    New!
    Sale
    Twisted X Boots MDMS003(
Men's) -
Dusty Tan Leather
    Sale
    $64.99
    $104.99 38% 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
    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
    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
    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
    $49.99
    $85.00 41% 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
    Timberland Classic TBLŪ Chukka (Men's)
    Timberland Classic TBLŪ Chukka (Men's)
    New!
    Sale
    Timberland Classic TBLŪ Chukka(
Men's) -
Wheat Nubuck Leather
    Sale
    $104.95
    $135.00 22% 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
    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
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    New!
    Sale
    Eastland Seneca(
Men's) -
Tan Waxee Leather
    Sale
    $99.95 - $109.95
    $110.00 up to 9% 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