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    Discount Mens Chukka Boots

    1-36 of 78 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
    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
    $88.95
    $160.00 44% off
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    New!
    Sale
    Clarks Wallabee(
Men's) -
Terracotta Suede
    Sale
    $53.95 - $139.95
    $135.00 - $140.00 up to 60% 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
    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) -
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 - $124.95
    $125.00 up to 16% 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
    Rockport Rugged Bucks Waterproof Boot (Men's)
    Rockport Rugged Bucks Waterproof Boot (Men's)
    Rockport Rugged Bucks Waterproof Boot (Men's)
    New!
    Sale
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Boston Tan
    Sale
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Tan Full Grain Leather
    Sale
    $109.95 - $119.95
    $120.00 up to 8% 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
    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
    Dr. Martens Sussex 3 Eye Chukka (Men's)
    Dr. Martens Sussex 3 Eye Chukka (Men's)
    Dr. Martens Sussex 3 Eye Chukka (Men's)
    New!
    Sale
    Dr. Martens Sussex 3 Eye Chukka(
Men's) -
Black Bear Track
    Sale
    Dr. Martens Sussex 3 Eye Chukka(
Men's) -
Dark Brown Bear Track
    Sale
    $84.98
    $95.00 11% 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
    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
    IZOD Nocturne Chukka Boot (Men's)
    IZOD Nocturne Chukka Boot (Men's)
    IZOD Nocturne Chukka Boot (Men's)
    IZOD Nocturne Chukka Boot (Men's)
    New!
    Sale
    IZOD Nocturne Chukka Boot(
Men's) -
Black Soft Calf PU
    Sale
    IZOD Nocturne Chukka Boot(
Men's) -
Dark Brown Tumble PU
    Sale
    IZOD Nocturne Chukka Boot(
Men's) -
Tan Burnished Calf PU
    Sale
    $55.45
    $65.00 15% 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
    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
    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
    $103.95 - $139.95
    $140.00 up to 26% 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
    Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
    Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
    Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
    Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
    Stacy Adams Dabney Plain Toe Chukka Boot 24977 (Men's)
    New!
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(
Men's) -
Black Suede Suede
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(
Men's) -
Brown Suede Suede
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(
Men's) -
Chestnut Suede
    Sale
    Stacy Adams Dabney Plain Toe Chukka Boot 24977(
Men's) -
Navy Suede
    Sale
    $67.45
    $100.00 33% off
    Rockport Path To Greatness High Chukka Boot (Men's)
    Rockport Path To Greatness High Chukka Boot (Men's)
    Rockport Path To Greatness High Chukka Boot (Men's)
    Rockport Path To Greatness High Chukka Boot (Men's)
    New!
    Sale
    Rockport Path To Greatness High Chukka Boot(
Men's) -
Grey Leather
    Sale
    Rockport Path To Greatness High Chukka Boot(
Men's) -
New Dress Blues Leather
    Sale
    Rockport Path To Greatness High Chukka Boot(
Men's) -
Tan Leather
    Sale
    $99.99
    $130.00 23% 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
    Timberland Classic TBLŪ Chukka (Men's)
    Timberland Classic TBLŪ Chukka (Men's)
    New!
    Sale
    Timberland Classic TBLŪ Chukka(
Men's) -
Wheat Nubuck Leather
    Sale
    $109.95
    $135.00 19% 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
    Stacy Adams Beckett Cap Toe Chukka Boot 24984 (Men's)
    Stacy Adams Beckett Cap Toe Chukka Boot 24984 (Men's)
    Stacy Adams Beckett Cap Toe Chukka Boot 24984 (Men's)
    New!
    Sale
    Stacy Adams Beckett Cap Toe Chukka Boot 24984(
Men's) -
Black Leather
    Sale
    Stacy Adams Beckett Cap Toe Chukka Boot 24984(
Men's) -
Brown Leather
    Sale
    $66.45
    $105.00 37% 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
    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
    $110.95 - $149.95
    $140.00 - $150.00 up to 26% 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
    Dr. Martens Esteem 4 Eye Chukka Industrial Boot (Men's)
    Dr. Martens Esteem 4 Eye Chukka Industrial Boot (Men's)
    Dr. Martens Esteem 4 Eye Chukka Industrial Boot (Men's)
    New!
    Sale
    Dr. Martens Esteem 4 Eye Chukka Industrial Boot(
Men's) -
Black Pitstop Leather
    Sale
    Dr. Martens Esteem 4 Eye Chukka Industrial Boot(
Men's) -
Teak Pitstop Leather
    Sale
    $99.98
    $110.00 9% 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
    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
    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
    Andrew Marc Dorchester Chukka SE (Men's)
    Andrew Marc Dorchester Chukka SE (Men's)
    Andrew Marc Dorchester Chukka SE (Men's)
    New!
    Sale
    Andrew Marc Dorchester Chukka SE(
Men's) -
Black/Deep Natural/Natural Suede
    Sale
    Andrew Marc Dorchester Chukka SE(
Men's) -
Dark Charcoal/Black/Dark Natural/Natural Suede
    Sale
    $89.00
    $178.00 50% off
    Stacy Adams Astro 53404 (Men's)
    Stacy Adams Astro 53404 (Men's)
    New!
    Sale
    Stacy Adams Astro 53404(
Men's) -
Black Smooth Leather
    Sale
    $62.95 - $89.95
    $90.00 up to 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
    Teva Durban Boot Leather (Men's)
    Teva Durban Boot Leather (Men's)
    New!
    Sale
    Teva Durban Boot Leather(
Men's) -
Eiffel Tower
    Sale
    $95.95 - $130.00
    $130.00 up to 26% off