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    Discount Mens Chukka Boots

    1-36 of 71 results
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    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
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(
Men's) -
Sand SixtyFive Suede
    Sale
    Clarks Desert Boot(
Men's) -
Sand Somerset
    Sale
    $82.45 - $180.45
    $130.00 - $400.00 up to 55% 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
    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
    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
    UGG Neumel Boot (Men's)
    UGG Neumel Boot (Men's)
    New!
    Sale
    UGG Neumel Boot(
Men's) -
Chestnut
    Sale
    $110.95
    $140.00 21% 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
    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
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Harken Chukka Boot(
Men's) -
Cognac Leather
    Sale
    $84.95 - $89.95
    $90.00 up to 6% off
    Johnston & Murphy McGuffey Chukka Boot (Men's)
    Johnston & Murphy McGuffey Chukka Boot (Men's)
    Johnston & Murphy McGuffey Chukka Boot (Men's)
    Johnston & Murphy McGuffey Chukka Boot (Men's)
    Johnston & Murphy McGuffey Chukka Boot (Men's)
    Johnston & Murphy McGuffey Chukka Boot (Men's)
    New!
    Sale
    Johnston & Murphy McGuffey Chukka Boot(
Men's) -
Chocolate Suede
    Sale
    Johnston & Murphy McGuffey Chukka Boot(
Men's) -
Gray Suede
    Sale
    Johnston & Murphy McGuffey Chukka Boot(
Men's) -
Navy Suede
    Sale
    Johnston & Murphy McGuffey Chukka Boot(
Men's) -
Olive Suede
    Sale
    Johnston & Murphy McGuffey Chukka Boot(
Men's) -
Taupe Suede
    Sale
    $104.95
    $125.00 16% 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
    $120.00 25% 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
    Mark Nason Skechers Holford Chukka Boot (Men's)
    Mark Nason Skechers Holford Chukka Boot (Men's)
    New!
    Sale
    Mark Nason Skechers Holford Chukka Boot(
Men's) -
Charcoal
    Sale
    $62.45 - $114.95
    $115.00 up to 46% off
    Merrell All Out Blazer Chukka (Men's)
    Merrell All Out Blazer Chukka (Men's)
    New!
    Sale
    Merrell All Out Blazer Chukka(
Men's) -
Black
    Sale
    $116.95 - $129.95
    $130.00 up to 10% 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
    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
    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
    Nunn Bush Tomah Ankle Boot (Men's)
    Nunn Bush Tomah Ankle Boot (Men's)
    Nunn Bush Tomah Ankle Boot (Men's)
    New!
    Sale
    Nunn Bush Tomah Ankle Boot(
Men's) -
Brown Suede
    Sale
    Nunn Bush Tomah Ankle Boot(
Men's) -
Sand Suede
    Sale
    $64.00
    $80.00 20% 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
    $172.95 - $229.95
    $230.00 up to 25% 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
    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 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
    Rockport Ledge Hill Too Chukka Boot (Men's)
    Rockport Ledge Hill Too Chukka Boot (Men's)
    New!
    Sale
    Rockport Ledge Hill Too Chukka Boot(
Men's) -
Black Leather
    Sale
    $112.95 - $149.95
    $140.00 - $150.00 up to 25% off
    Steve Madden Hestonn (Men's)
    Steve Madden Hestonn (Men's)
    Steve Madden Hestonn (Men's)
    New!
    Sale
    Steve Madden Hestonn(
Men's) -
Grey Leather
    Sale
    Steve Madden Hestonn(
Men's) -
Tan Leather
    Sale
    $53.95 - $65.95
    $90.00 up to 40% 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
    Nunn Bush Robinson Chukka Boot (Men's)
    Nunn Bush Robinson Chukka Boot (Men's)
    Nunn Bush Robinson Chukka Boot (Men's)
    New!
    Sale
    Nunn Bush Robinson Chukka Boot(
Men's) -
Black Leather
    Sale
    Nunn Bush Robinson Chukka Boot(
Men's) -
Chestnut Leather
    Sale
    $72.00
    $90.00 20% 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
    Merrell Freewheel Bolt Chukka (Men's)
    Merrell Freewheel Bolt Chukka (Men's)
    New!
    Sale
    Merrell Freewheel Bolt Chukka(
Men's) -
Coriander
    Sale
    $98.95 - $109.95
    $110.00 up to 10% 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
    $200.95
    $268.00 25% 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 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
    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
    $125.00 34% 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
    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
    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