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    Mens Chukka Boots

    1-36 of 262 results
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    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
    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)
    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) -
Camel Leather
    New
    Clarks Wallabee Boot(
Men's) -
Brown Tumbled Leather
    Sale
    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) -
Dark Green Suede
    New
    Clarks Wallabee Boot(
Men's) -
Maple Suede
    Clarks Wallabee Boot(
Men's) -
Petrol Blue Leather
    New
    Clarks Wallabee Boot(
Men's) -
Rust Leather
    Clarks Wallabee Boot(
Men's) -
Rust Vintage Suede
    New
    $52.95 - $199.95
    $140.00 - $200.00 up to 62% 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)
    New!
    Sale
    Clarks Desert Boot(
Men's) -
Bronze Nubuck
    New
    Clarks Desert Boot(
Men's) -
Camel Leather
    New
    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) -
Charcoal Suede
    New
    Clarks Desert Boot(
Men's) -
Dark Green Suede
    New
    Clarks Desert Boot(
Men's) -
Dark Tan Suede
    New
    Clarks Desert Boot(
Men's) -
Dark Taupe Nubuck
    New
    Clarks Desert Boot(
Men's) -
Navy Leather
    Clarks Desert Boot(
Men's) -
New Black Suede
    Clarks Desert Boot(
Men's) -
Nut Brown Suede
    New
    Clarks Desert Boot(
Men's) -
Rust Leather
    Clarks Desert Boot(
Men's) -
Taupe Distressed Suede
    $129.95 - $179.95
    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)
    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
    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
    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
    Tsubo Beale (Men's)
    Tsubo Beale (Men's)
    New!
    Sale
    Tsubo Beale(
Men's) -
Black Leather
    Sale
    $37.95
    $150.00 75% off
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    Rockport Total Motion Fusion Desert Boot (Men's)
    New!
    Sale
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Dark Bitter Chocolate 2 Suede
    New
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Black
    Rockport Total Motion Fusion Desert Boot(
Men's) -
New Dress Blues
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Rocksand
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Tan
    $149.95
    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
    Steve Madden Harken Chukka (Men's)
    Steve Madden Harken Chukka (Men's)
    Steve Madden Harken Chukka (Men's)
    Steve Madden Harken Chukka (Men's)
    New!
    Sale
    Steve Madden Harken Chukka(
Men's) -
Black Multi Leather/Fabric
    New
    Steve Madden Harken Chukka(
Men's) -
Brown Multi Leather/Fabric
    New
    Steve Madden Harken Chukka(
Men's) -
Cognac Leather
    Sale
    $84.95 - $89.95
    $90.00 up to 6% off
    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 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) -
Dark Tan Suede
    New
    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) -
Maple Suede
    $134.95 - $139.95
    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) -
Tan Full Grain Leather
    Sale
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
New Dress Blues Leather
    New
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Wheat Nubuck
    $109.95 - $119.95
    $120.00 up to 8% off
    Born Harrison (Men's)
    Born Harrison (Men's)
    Born Harrison (Men's)
    Born Harrison (Men's)
    New!
    Sale
    Born Harrison(
Men's) -
Castagno Full Grain Leather
    Born Harrison(
Men's) -
Chestnut Full Grain Leather
    Born Harrison(
Men's) -
Peltro Full Grain Leather
    $109.95
    Dr. Martens Lea 4-Eye Chukka Boot (Men's)
    Dr. Martens Lea 4-Eye Chukka Boot (Men's)
    Dr. Martens Lea 4-Eye Chukka Boot (Men's)
    Dr. Martens Lea 4-Eye Chukka Boot (Men's)
    New!
    Sale
    Dr. Martens Lea 4-Eye Chukka Boot(
Men's) -
Black Grizzly
    Dr. Martens Lea 4-Eye Chukka Boot(
Men's) -
Dark Brown Grizzly
    Dr. Martens Lea 4-Eye Chukka Boot(
Men's) -
Tan/Biscuit Grizzly
    $114.95
    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) -
Wheat Suede
    $89.95 - $99.95
    $100.00 up to 10% off
    Dr. Martens Mayport 2-Eye Desert Boot (Men's)
    Dr. Martens Mayport 2-Eye Desert Boot (Men's)
    Dr. Martens Mayport 2-Eye Desert Boot (Men's)
    Dr. Martens Mayport 2-Eye Desert Boot (Men's)
    Dr. Martens Mayport 2-Eye Desert Boot (Men's)
    Dr. Martens Mayport 2-Eye Desert Boot (Men's)
    Dr. Martens Mayport 2-Eye Desert Boot (Men's)
    Dr. Martens Mayport 2-Eye Desert Boot (Men's)
    New!
    Sale
    Dr. Martens Mayport 2-Eye Desert Boot(
Men's) -
Black Overdyed Twill Canvas
    Dr. Martens Mayport 2-Eye Desert Boot(
Men's) -
Dark Brown Overdyed Twill Canvas
    Dr. Martens Mayport 2-Eye Desert Boot(
Men's) -
Forest Overdyed Twill Canvas
    Dr. Martens Mayport 2-Eye Desert Boot(
Men's) -
Navy Overdyed Twill Canvas
    Dr. Martens Mayport 2-Eye Desert Boot(
Men's) -
Old Oxblood Overdyed Twill Canvas
    Dr. Martens Mayport 2-Eye Desert Boot(
Men's) -
Olive Overdyed Twill Canvas
    Dr. Martens Mayport 2-Eye Desert Boot(
Men's) -
Sand Overdyed Twill Canvas
    $72.45 - $74.95
    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
    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
    Rockport Ledge Hill Too Chukka Boot(
Men's) -
Dark Brown Leather
    $139.95 - $149.95
    Dr. Martens Barnie Chukka Boot (Men's)
    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) -
Black Overdrive
    Dr. Martens Barnie Chukka Boot(
Men's) -
Dark Brown Grizzly
    Sale
    $89.95 - $119.95
    $120.00 up to 25% 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
    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
    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) -
Oily Coal Nubuck
    New
    Naot Pilot(
Men's) -
Blue Velvet Suede
    Naot Pilot(
Men's) -
Gray Suede
    Naot Pilot(
Men's) -
Seal Brown Suede
    Naot Pilot(
Men's) -
Vintage Grey Leather
    $199.95 - $239.95
    Stacy Adams Astro 53404 (Men's)
    Stacy Adams Astro 53404 (Men's)
    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) -
Black Suede
    Stacy Adams Astro 53404(
Men's) -
Brown Suede
    Sale
    Stacy Adams Astro 53404(
Men's) -
Gray Suede
    Sale
    Stacy Adams Astro 53404(
Men's) -
Sand Suede
    $77.95 - $89.95
    $90.00 up to 13% 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)
    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