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    Mens Chukka Boots

    1-36 of 294 results
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    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) -
Khaki Leather
    New
    Clarks Desert Boot(
Men's) -
Multicolour Suede
    New
    Clarks Desert Boot(
Men's) -
Amber Gold
    Sale
    Clarks Desert Boot(
Men's) -
Beeswax
    Clarks Desert Boot(
Men's) -
Black Smooth
    Clarks Desert Boot(
Men's) -
Bronze Nubuck
    Clarks Desert Boot(
Men's) -
Brown
    Clarks Desert Boot(
Men's) -
Camel Leather
    Clarks Desert Boot(
Men's) -
Charcoal Suede
    Clarks Desert Boot(
Men's) -
Dark Green Suede
    Clarks Desert Boot(
Men's) -
Dark Tan Suede
    Clarks Desert Boot(
Men's) -
Dark Taupe Nubuck
    Clarks Desert Boot(
Men's) -
Navy Leather
    Clarks Desert Boot(
Men's) -
New Black Suede
    Clarks Desert Boot(
Men's) -
Nut Brown 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) -
Wolf Suede
    New
    $105.45 - $179.95
    $130.00 - $180.00 up to 19% off
    Florsheim Mogul Chukka Boot II (Men's)
    Florsheim Mogul Chukka Boot II (Men's)
    Florsheim Mogul Chukka Boot II (Men's)
    New!
    Sale
    Florsheim Mogul Chukka Boot II(
Men's) -
Black Smooth Leather
    New
    Florsheim Mogul Chukka Boot II(
Men's) -
Cognac Smooth Leather
    New
    $119.95
    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
    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) -
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
    Johnston & Murphy Copeland Chukka Boot(
Men's) -
Taupe Water-Resistant Suede
    $149.95 - $154.95
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    Clarks Stinson Hi Moc Toe Boot (Men's)
    New!
    Sale
    Clarks Stinson Hi Moc Toe Boot(
Men's) -
Beeswax Leather
    Clarks Stinson Hi Moc Toe Boot(
Men's) -
Black Oily Leather
    Clarks Stinson Hi Moc Toe Boot(
Men's) -
Black Suede
    Clarks Stinson Hi Moc Toe Boot(
Men's) -
Brown Oily Leather
    Clarks Stinson Hi Moc Toe Boot(
Men's) -
Sand Suede
    $99.95
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    Clarks Wallabee (Men's)
    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) -
Cola
    Clarks Wallabee(
Men's) -
Dark Tan Suede
    Clarks Wallabee(
Men's) -
Maple Suede
    $53.95 - $139.95
    $135.00 - $140.00 up to 60% 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 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) -
Multicolour 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) -
Bronze Suede
    Clarks Wallabee Boot(
Men's) -
Dark Brown Suede
    Clarks Wallabee Boot(
Men's) -
Dark Green Suede
    Clarks Wallabee Boot(
Men's) -
Maple Suede
    Clarks Wallabee Boot(
Men's) -
Navy Leather
    Clarks Wallabee Boot(
Men's) -
Petrol Blue Leather
    Clarks Wallabee Boot(
Men's) -
Rust Vintage Suede
    $139.95 - $199.95
    Naot Pilot (Men's)
    Naot Pilot (Men's)
    Naot Pilot (Men's)
    Naot Pilot (Men's)
    Naot Pilot (Men's)
    Naot Pilot (Men's)
    Naot Pilot (Men's)
    New!
    Sale
    Naot Pilot(
Men's) -
Blue Velvet Suede
    Naot Pilot(
Men's) -
Brown Gradient Handcrafted Leather
    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
    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
    $139.95
    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
    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 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) -
Black
    Rockport Total Motion Fusion Desert Boot(
Men's) -
Dark Bitter Chocolate 2 Suede
    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
    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
    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
    Johnston & Murphy Wallace Chukka Boot(
Men's) -
Gray Water-Resistant Suede
    Johnston & Murphy Wallace Chukka Boot(
Men's) -
Navy Water-Resistant Suede
    Johnston & Murphy Wallace Chukka Boot(
Men's) -
Taupe Water-Resistant Suede
    $124.95
    Florsheim Castellano Chukka (Men's)
    Florsheim Castellano Chukka (Men's)
    Florsheim Castellano Chukka (Men's)
    Florsheim Castellano Chukka (Men's)
    New!
    Sale
    Florsheim Castellano Chukka(
Men's) -
Black Leather
    Florsheim Castellano Chukka(
Men's) -
Brown Leather
    Florsheim Castellano Chukka(
Men's) -
Saddle Tan Leather
    $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)
    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) -
Castlerock Grey
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Tan Full Grain Leather
    Sale
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Espresso Nubuck
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
New Dress Blues Leather
    Rockport Rugged Bucks Waterproof Boot(
Men's) -
Wheat Nubuck
    $109.95 - $119.95
    $120.00 up to 8% off
    Timberland Earthkeepers Brook Park Chukka (Men's)
    Timberland Earthkeepers Brook Park Chukka (Men's)
    Timberland Earthkeepers Brook Park Chukka (Men's)
    Timberland Earthkeepers Brook Park Chukka (Men's)
    New!
    Sale
    Timberland Earthkeepers Brook Park Chukka(
Men's) -
Black Smooth
    Timberland Earthkeepers Brook Park Chukka(
Men's) -
Brown Smooth
    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)
    Steve Madden Harken Chukka Boot (Men's)
    Steve Madden Harken Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Harken Chukka Boot(
Men's) -
Black Multi Leather/Fabric
    Steve Madden Harken Chukka Boot(
Men's) -
Brown Multi Leather/Fabric
    Steve Madden Harken Chukka Boot(
Men's) -
Cognac Leather
    Sale
    $84.95 - $89.95
    $90.00 up to 6% 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
    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
    Timberland Grantly Chukka Boot (Men's)
    Timberland Grantly Chukka Boot (Men's)
    Timberland Grantly Chukka Boot (Men's)
    Timberland Grantly Chukka Boot (Men's)
    New!
    Sale
    Timberland Grantly Chukka Boot(
Men's) -
Black Full Grain Leather/Suede
    Timberland Grantly Chukka Boot(
Men's) -
Brown Full Grain Leather/Suede
    Timberland Grantly Chukka Boot(
Men's) -
Dark Brown Full Grain Leather/Suede
    $139.95
    Steve Madden Hendric Chukka Boot (Men's)
    Steve Madden Hendric Chukka Boot (Men's)
    Steve Madden Hendric Chukka Boot (Men's)
    Steve Madden Hendric Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Hendric Chukka Boot(
Men's) -
Green Suede/Leather
    New
    Steve Madden Hendric Chukka Boot(
Men's) -
Navy Suede/Leather
    New
    Steve Madden Hendric Chukka Boot(
Men's) -
Tan Suede/Leather
    New
    $89.95
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    Timberland Newport Bay Chukka Boot (Men's)
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    With tough, rugged Goodyear welt construction, the Colorado is an all purpose boot that features nylon mesh lining, Poliyou sock ...
    Caterpillar Colorado (Men's)
    Description:
    With tough, rugged Goodyear welt construction, the Colorado is an all purpose boot that features nylon mesh lining, Poliyou sock liner, PVC midsole, and T3 outsole. Additional Info Polka Dot , Nubuck , Cheetah Print , Goodyear Welt , Full ...
    Stylish, tough and resilient, the Wilson low plain toe boot features a canvas padded collar, leather and lightweight canvas lining, ...
    Andrew Marc Wilson (Men's)
    Description:
    Stylish, tough and resilient, the Wilson low plain toe boot features a canvas padded collar, leather and lightweight canvas lining, waxy finish laces, leather welt and outsole. Additional Info Leather Heel Height: 1" Fit: True to Size Upper: Leather Imported ...