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    Mens Chukka Boots

    1-36 of 300 results
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    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    Clarks Wallabee Boot (Men's)
    New!
    Sale
    Clarks Wallabee Boot(
Men's) -
Bronze Suede
    New
    Clarks Wallabee Boot(
Men's) -
Dark Green Suede
    New
    Clarks Wallabee Boot(
Men's) -
Beeswax/Beeswax Leather
    Clarks Wallabee Boot(
Men's) -
Black/Black Leather
    Clarks Wallabee Boot(
Men's) -
Black/Black Suede
    Clarks Wallabee Boot(
Men's) -
Dark Brown Suede
    Clarks Wallabee Boot(
Men's) -
Maple Suede
    Clarks Wallabee Boot(
Men's) -
Petrol Blue Leather
    New
    Clarks Wallabee Boot(
Men's) -
Rust Vintage Suede
    New
    $127.95 - $199.95
    $140.00 - $200.00 up to 9% off
    UGG Freamon Chukka Boot (Men's)
    UGG Freamon Chukka Boot (Men's)
    UGG Freamon Chukka Boot (Men's)
    UGG Freamon Chukka Boot (Men's)
    UGG Freamon Chukka Boot (Men's)
    New!
    Sale
    UGG Freamon Chukka Boot(
Men's) -
Black Suede
    UGG Freamon Chukka Boot(
Men's) -
Chestnut/White
    UGG Freamon Chukka Boot(
Men's) -
New Navy Suede
    UGG Freamon Chukka Boot(
Men's) -
Seal Suede
    $82.95 - $86.95
    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 Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    New!
    Sale
    Clarks Wallabee(
Men's) -
Camel Suede
    New
    Clarks Wallabee(
Men's) -
Charcoal Suede
    New
    Clarks Wallabee(
Men's) -
Terracotta Suede
    Sale
    Clarks Wallabee(
Men's) -
Beeswax/Beeswax Leather
    Clarks Wallabee(
Men's) -
Black/Black Leather
    Clarks Wallabee(
Men's) -
Brown Tumbled Leather
    Clarks Wallabee(
Men's) -
Dark Tan Suede
    New
    Clarks Wallabee(
Men's) -
Maple Suede
    $90.45 - $139.95
    $135.00 - $140.00 up to 33% off
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    Clarks Desert Boot (Men's)
    New!
    Sale
    Clarks Desert Boot(
Men's) -
Bronze Nubuck
    New
    Clarks Desert Boot(
Men's) -
Camel Leather
    New
    Clarks Desert Boot(
Men's) -
Sand SixtyFive Suede
    Sale
    Clarks Desert Boot(
Men's) -
Sand Somerset
    Sale
    Clarks Desert Boot(
Men's) -
Amber Gold
    Clarks Desert Boot(
Men's) -
Beeswax
    Clarks Desert Boot(
Men's) -
Black Smooth
    Clarks Desert Boot(
Men's) -
Brown
    Clarks Desert Boot(
Men's) -
Dark Tan Suede
    New
    Clarks Desert Boot(
Men's) -
Dark Taupe Nubuck
    New
    Clarks Desert Boot(
Men's) -
Khaki Leather
    New
    Clarks Desert Boot(
Men's) -
Multicolour Suede
    New
    Clarks Desert Boot(
Men's) -
Navy Leather
    Clarks Desert Boot(
Men's) -
New Black Suede
    Clarks Desert Boot(
Men's) -
Off White Interest Suede
    Clarks Desert Boot(
Men's) -
Petrol Blue Leather
    New
    Clarks Desert Boot(
Men's) -
Rust Leather
    Clarks Desert Boot(
Men's) -
Taupe Distressed Suede
    Clarks Desert Boot(
Men's) -
Terracotta Suede
    Clarks Desert Boot(
Men's) -
Wolf Suede
    New
    $82.45 - $180.45
    $130.00 - $400.00 up to 55% off
    Dansko Jake Plain Toe Chukka Boot (Men's)
    Dansko Jake Plain Toe Chukka Boot (Men's)
    Dansko Jake Plain Toe Chukka Boot (Men's)
    New!
    Sale
    Dansko Jake Plain Toe Chukka Boot(
Men's) -
Black Antiqued Calf
    New
    Dansko Jake Plain Toe Chukka Boot(
Men's) -
Taupe Milled Nubuck
    New
    $194.95
    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
    Naot Pilot (Men's)
    Naot Pilot (Men's)
    Naot Pilot (Men's)
    Naot Pilot (Men's)
    Naot Pilot (Men's)
    Naot Pilot (Men's)
    New!
    Sale
    Naot Pilot(
Men's) -
Blue Velvet Suede
    Naot Pilot(
Men's) -
Gray Suede
    Naot Pilot(
Men's) -
Oily Coal Nubuck
    Naot Pilot(
Men's) -
Seal Brown Suede
    Naot Pilot(
Men's) -
Vintage Grey Leather
    $199.95 - $239.95
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    Eastland Seneca (Men's)
    New!
    Sale
    Eastland Seneca(
Men's) -
Bomber Brown Leather
    Eastland Seneca(
Men's) -
Gray Leather
    Eastland Seneca(
Men's) -
Tan Waxee Leather
    Sale
    Eastland Seneca(
Men's) -
Natural Leather
    Eastland Seneca(
Men's) -
Navy Leather
    Eastland Seneca(
Men's) -
Peanut Leather
    $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)
    UGG Neumel Boot (Men's)
    New!
    Sale
    UGG Neumel Boot(
Men's) -
Chestnut
    Sale
    UGG Neumel Boot(
Men's) -
China Tea
    $110.95
    $140.00 21% off
    Johnston & Murphy Wallace Chukka Boot (Men's)
    Johnston & Murphy Wallace Chukka Boot (Men's)
    Johnston & Murphy Wallace Chukka Boot (Men's)
    Johnston & Murphy Wallace Chukka Boot (Men's)
    Johnston & Murphy Wallace Chukka Boot (Men's)
    New!
    Sale
    Johnston & Murphy Wallace Chukka Boot(
Men's) -
Dark Brown Water-Resistant Suede
    New
    Johnston & Murphy Wallace Chukka Boot(
Men's) -
Gray Water-Resistant Suede
    New
    Johnston & Murphy Wallace Chukka Boot(
Men's) -
Navy Water-Resistant Suede
    New
    Johnston & Murphy Wallace Chukka Boot(
Men's) -
Taupe Water-Resistant Suede
    New
    $124.95
    Clarks Stinson Hi (Men's)
    Clarks Stinson Hi (Men's)
    Clarks Stinson Hi (Men's)
    Clarks Stinson Hi (Men's)
    Clarks Stinson Hi (Men's)
    Clarks Stinson Hi (Men's)
    New!
    Sale
    Clarks Stinson Hi(
Men's) -
Beeswax Leather
    Clarks Stinson Hi(
Men's) -
Black Oily Leather
    Clarks Stinson Hi(
Men's) -
Black Suede
    Clarks Stinson Hi(
Men's) -
Brown Oily Leather
    Clarks Stinson Hi(
Men's) -
Sand Suede
    $99.95
    Altra Footwear Desert Chukka Boot (Men's)
    Altra Footwear Desert Chukka Boot (Men's)
    Altra Footwear Desert Chukka Boot (Men's)
    Altra Footwear Desert Chukka Boot (Men's)
    New!
    Sale
    Altra Footwear Desert Chukka Boot(
Men's) -
Black/Gray
    New
    Altra Footwear Desert Chukka Boot(
Men's) -
Blue/Lime
    New
    Altra Footwear Desert Chukka Boot(
Men's) -
Taupe
    New
    $119.95
    Clarks Stinson Lo (Men's)
    Clarks Stinson Lo (Men's)
    Clarks Stinson Lo (Men's)
    New!
    Sale
    Clarks Stinson Lo(
Men's) -
Beeswax Leather
    Sale
    Clarks Stinson Lo(
Men's) -
Black Leather
    $89.95 - $99.95
    $100.00 up to 10% off
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    Johnston & Murphy Copeland Chukka Boot (Men's)
    New!
    Sale
    Johnston & Murphy Copeland Chukka Boot(
Men's) -
Taupe Water-Resistant Suede
    New
    Johnston & Murphy Copeland Chukka Boot(
Men's) -
Black Tumbled Full Grain Leather
    Johnston & Murphy Copeland Chukka Boot(
Men's) -
Camel Suede
    Johnston & Murphy Copeland Chukka Boot(
Men's) -
Dark Gray Suede
    Johnston & Murphy Copeland Chukka Boot(
Men's) -
Navy Suede
    Johnston & Murphy Copeland Chukka Boot(
Men's) -
Red Brown Oiled Full Grain Leather
    Johnston & Murphy Copeland Chukka Boot(
Men's) -
Tan Oiled Full Grain
    $149.95 - $154.95
    Dr. Martens Bonny 6 Eye Chukka Boot
    Dr. Martens Bonny 6 Eye Chukka Boot
    Dr. Martens Bonny 6 Eye Chukka Boot
    Dr. Martens Bonny 6 Eye Chukka Boot
    Dr. Martens Bonny 6 Eye Chukka Boot
    New!
    Sale
    Dr. Martens Bonny 6 Eye Chukka Boot -
Army Green 16oz Washed Canvas/Kanga S
    New
    Dr. Martens Bonny 6 Eye Chukka Boot -
Black 12oz Waxy Canvas/Kanga S
    New
    Dr. Martens Bonny 6 Eye Chukka Boot -
Charcoal Extra Tough Nylon/Rubbery
    Dr. Martens Bonny 6 Eye Chukka Boot -
Old Oxblood Extra Tough Nylon/Rubbery
    $79.95 - $84.95
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Harken Chukka Boot(
Men's) -
Brown Multi Leather/Fabric
    New
    Steve Madden Harken Chukka Boot(
Men's) -
Black Multi Leather/Fabric
    Steve Madden Harken Chukka Boot(
Men's) -
Cognac Leather
    Sale
    $84.95 - $89.95
    $90.00 up to 6% off
    Rockport Rugged Bucks Waterproof Boot (Men's)
    Rockport Rugged Bucks Waterproof Boot (Men's)
    Rockport Rugged Bucks Waterproof Boot (Men's)
    Rockport Rugged Bucks Waterproof Boot (Men's)
    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
    New
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Castlerock Grey
    New
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Espresso Nubuck
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
New Dress Blues Leather
    New
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Tan Full Grain Leather
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Wheat Nubuck
    $119.95
    Born Jax (Men's)
    Born Jax (Men's)
    Born Jax (Men's)
    New!
    Sale
    Born Jax(
Men's) -
Brown Full Grain Leather
    Born Jax(
Men's) -
Tan Full Grain Leather
    $108.95 - $109.95
    Rockport Ledge Hill Too Chukka Boot (Men's)
    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
    Rockport Ledge Hill Too Chukka Boot(
Men's) -
Dark Brown Leather
    $112.95 - $149.95
    $140.00 - $150.00 up to 25% off
    Rockport Charson Lace Up Ankle Boot (Men's)
    Rockport Charson Lace Up Ankle Boot (Men's)
    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) -
Black Leather
    Rockport Charson Lace Up Ankle Boot(
Men's) -
Chocolate Leather
    Rockport Charson Lace Up Ankle Boot(
Men's) -
Dark Brown Leather
    Sale
    $109.95 - $139.95
    $140.00 up to 21% 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
    Florsheim Doon Chukka (Men's)
    Florsheim Doon Chukka (Men's)
    Florsheim Doon Chukka (Men's)
    New!
    Sale
    Florsheim Doon Chukka(
Men's) -
Black
    Florsheim Doon Chukka(
Men's) -
Brown Smooth
    $119.95
    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
    $89.95 - $104.95
    $125.00 up to 28% off
    Hush Puppies Bridgeport (Men's)
    Hush Puppies Bridgeport (Men's)
    Hush Puppies Bridgeport (Men's)
    Hush Puppies Bridgeport (Men's)
    Hush Puppies Bridgeport (Men's)
    New!
    Sale
    Hush Puppies Bridgeport(
Men's) -
Black Leather
    Hush Puppies Bridgeport(
Men's) -
Black Suede
    Hush Puppies Bridgeport(
Men's) -
Taupe Suede
    Hush Puppies Bridgeport(
Men's) -
Classic Taupe Suede
    $109.95
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    Dr. Martens Maleke Padded Collar Boot (Men's)
    Description:
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    Versatile style with comfort to spare comes in the SKECHERS Relaxed Fit®: Segment - Barillo boot. Smooth leather upper in ...
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    Andrew Marc Dorchester Chukka (Men's)
    Description:
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