Phone
    Call
    1 (888) 200 - 8414
    Mon - Fri: 8:00 AM - Midnight ET
    Sat - Sun: 8:00 AM - 11:00 PM ET
    FREE shipping and FREE exchanges. every day. no minimum.
    0 Cart
    Loading...
    Your cart is currently unavailable
    Loading...
    Advanced search is currently unavailable

    Leather Chukka Boots

    1-36 of 183 results
     1 2 3 4 5 
    Sort by
    Display
    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
    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)
    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 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) -
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
    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 Desert Boot (Women's)
    Clarks Desert Boot (Women's)
    Clarks Desert Boot (Women's)
    Clarks Desert Boot (Women's)
    Clarks Desert Boot (Women's)
    New!
    Sale
    Clarks Desert Boot(
Women's) -
Beeswax Leather
    Clarks Desert Boot(
Women's) -
Black Suede
    Clarks Desert Boot(
Women's) -
Oakwood Suede
    Clarks Desert Boot(
Women's) -
Taupe Distressed
    $119.95 - $139.95
    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
    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
    UGG Neumel Boot (Men's)
    UGG Neumel Boot (Men's)
    UGG Neumel Boot (Men's)
    New!
    Sale
    UGG Neumel Boot(
Men's) -
Chestnut
    UGG Neumel Boot(
Men's) -
China Tea
    $139.95
    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
    Sale
    $109.95 - $139.95
    $140.00 up to 21% 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) -
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
    Sebago Hutton Chukka Boot (Women's)
    Sebago Hutton Chukka Boot (Women's)
    Sebago Hutton Chukka Boot (Women's)
    Sebago Hutton Chukka Boot (Women's)
    Sebago Hutton Chukka Boot (Women's)
    Sebago Hutton Chukka Boot (Women's)
    New!
    Sale
    Sebago Hutton Chukka Boot(
Women's) -
Dark Brown Suede/Tan Leather
    Sebago Hutton Chukka Boot(
Women's) -
Dark Taupe Suede/Tan Leather
    Sebago Hutton Chukka Boot(
Women's) -
Natural Linen/Textile
    Sebago Hutton Chukka Boot(
Women's) -
Navy Linen/Textile
    Sebago Hutton Chukka Boot(
Women's) -
Navy Suede/Tan Leather
    $144.95
    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
    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
    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
    Clarks Nevella Harper Chukka Boot (Women's)
    Clarks Nevella Harper Chukka Boot (Women's)
    Clarks Nevella Harper Chukka Boot (Women's)
    Clarks Nevella Harper Chukka Boot (Women's)
    New!
    Sale
    Clarks Nevella Harper Chukka Boot(
Women's) -
Aubergine Cow Suede
    New
    Clarks Nevella Harper Chukka Boot(
Women's) -
Black Leather
    New
    Clarks Nevella Harper Chukka Boot(
Women's) -
Khaki Cow Suede
    New
    $159.95
    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
    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
    Clarks Acre Bridge Chukka Boot (Women's)
    Clarks Acre Bridge Chukka Boot (Women's)
    Clarks Acre Bridge Chukka Boot (Women's)
    New!
    Sale
    Clarks Acre Bridge Chukka Boot(
Women's) -
Sand Cow Suede
    New
    Clarks Acre Bridge Chukka Boot(
Women's) -
Tan Cow Full Grain Leather
    New
    $94.95
    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 Stratton Limit (Men's)
    Clarks Stratton Limit (Men's)
    Clarks Stratton Limit (Men's)
    New!
    Sale
    Clarks Stratton Limit(
Men's) -
Black Leather
    Clarks Stratton Limit(
Men's) -
Brown Leather
    $134.95
    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
    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
    Steve Madden Inflict Chukka Boot (Men's)
    Steve Madden Inflict Chukka Boot (Men's)
    Steve Madden Inflict Chukka Boot (Men's)
    Steve Madden Inflict Chukka Boot (Men's)
    New!
    Sale
    Steve Madden Inflict Chukka Boot(
Men's) -
Black Leather
    Steve Madden Inflict Chukka Boot(
Men's) -
Tan Leather
    Steve Madden Inflict Chukka Boot(
Men's) -
Wood Leather
    $99.95
    ECCO Turn GORE-TEX Boot (Men's)
    ECCO Turn GORE-TEX Boot (Men's)
    ECCO Turn GORE-TEX Boot (Men's)
    New!
    Sale
    ECCO Turn GORE-TEX Boot(
Men's) -
Coffee Lexi Leather
    ECCO Turn GORE-TEX Boot(
Men's) -
Mocha Oil Nubuck
    Sale
    $172.95 - $229.95
    $230.00 up to 25% off
    Related Products
    The Vito Caiman Wing-Tip Ankle Boot elevates a typical silhouette with luxurious touches, wing tip detailing, and impeccable craftsmanship. Genuine ...
    Belvedere Vito Caiman Wing-Tip Ankle Boot (Men's)
    Description:
    The Vito Caiman Wing-Tip Ankle Boot elevates a typical silhouette with luxurious touches, wing tip detailing, and impeccable craftsmanship. Genuine alligator and Italian leather upper. Additional Info Exotic , Low Heel , Alligator , Leather , Lace Up , Dress ...
    Handsewn by skilled shoemakers using a traditional true moccasin construction. Premium heavyweight upper and rawhide laces. Leather-lined, padded OrthoLite® comfort ...
    Eastland 1955 Edition Brooklyn 1955 Ankle Boot (Men's)
    Description:
    Handsewn by skilled shoemakers using a traditional true moccasin construction. Premium heavyweight upper and rawhide laces. Leather-lined, padded OrthoLite® comfort insole with patented moisture and odor control keeps you cool and dry all day. Full leather mid-sole. Genuine Vibram® 132 ...
    Look sophisticated wearing the Mezlan Bremen II Ankle Boot, a lace-up style with a cap toe and broguing details. This ...
    Mezlan Bremen II Ankle Boot (Men's)
    Description:
    Look sophisticated wearing the Mezlan Bremen II Ankle Boot, a lace-up style with a cap toe and broguing details. This shoe is equipped with a leather sole featuring rubber insets. The memory foam cushioning provides optimum comfort. Handmade in Spain. ...