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

Discount Chukka Boots

1-36 of 76 results
 1 2 3 
Sort by
Display
Clarks Bushacre 2 (Men's)
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) -
                                     Black Perforated Full Grain Leather
Sale
Clarks Bushacre 2(
                                      Men's) -
                                     Navy Leather
Sale
Clarks Bushacre 2(
                                      Men's) -
                                     Tan Leather
Sale
$73.95 - $99.95
$100.00 up to 26% off
Frye Oliver Chukka (Men's)
Frye Oliver Chukka (Men's)
New!
Sale
Frye Oliver Chukka(
                                      Men's) -
                                     Dark Brown Leather
Sale
$139.95
$278.00 50% 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
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
UGG Leighton Ankle Boot (Men's)
UGG Leighton Ankle Boot (Men's)
New!
Sale
UGG Leighton Ankle Boot(
                                      Men's) -
                                     Chocolate
Sale
$80.95 - $159.95
$160.00 up to 49% 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
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
Clarks Desert Boot (Women's)
Clarks Desert Boot (Women's)
Clarks Desert Boot (Women's)
New!
Sale
Clarks Desert Boot(
                                      Women's) -
                                     Blue/Grey Suede
Sale
Clarks Desert Boot(
                                      Women's) -
                                     Pale Green Suede
Sale
$73.95
$130.00 43% off
Clarks Hawkley Rise Chukka (Men's)
Clarks Hawkley Rise Chukka (Men's)
New!
Sale
Clarks Hawkley Rise Chukka(
                                      Men's) -
                                     Dark Brown Combi
Sale
$82.45 - $124.95
$125.00 up to 34% 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
Twisted X Boots MDM0020 (Men's)
Twisted X Boots MDM0020 (Men's)
New!
Sale
Twisted X Boots MDM0020(
                                      Men's) -
                                     Dusty Grey Leather
Sale
$60.49
$104.99 42% 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
Clarks Darble Mid Chukka (Men's)
Clarks Darble Mid Chukka (Men's)
New!
Sale
Clarks Darble Mid Chukka(
                                      Men's) -
                                     Cognac Leather
Sale
$98.95
$150.00 34% off
Clarks Garren Free Chukka Boot (Men's)
Clarks Garren Free Chukka Boot (Men's)
Clarks Garren Free Chukka Boot (Men's)
New!
Sale
Clarks Garren Free Chukka Boot(
                                      Men's) -
                                     Brown Full Grain Leather
Sale
Clarks Garren Free Chukka Boot(
                                      Men's) -
                                     Taupe Full Grain Leather
Sale
$73.95 - $82.45
$110.00 up to 33% off
Clarks Stinson Lo (Men's)
Clarks Stinson Lo (Men's)
New!
Sale
Clarks Stinson Lo(
                                      Men's) -
                                     Beeswax Leather
Sale
$89.95 - $99.95
$100.00 up to 10% off
White Mountain Irma Wedge Heel Bootie (Women's)
White Mountain Irma Wedge Heel Bootie (Women's)
White Mountain Irma Wedge Heel Bootie (Women's)
New!
Sale
White Mountain Irma Wedge Heel Bootie(
                                      Women's) -
                                     Black Suede
Sale
White Mountain Irma Wedge Heel Bootie(
                                      Women's) -
                                     Brown Suede
Sale
$46.95
$79.00 41% 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
Clarks Aerial Boot (Men's)
Clarks Aerial Boot (Men's)
New!
Sale
Clarks Aerial Boot(
                                      Men's) -
                                     Bronze/Brown Suede
Sale
$48.95
$140.00 65% off
Franco Sarto Tomcat Chukka Boot (Women's)
Franco Sarto Tomcat Chukka Boot (Women's)
Franco Sarto Tomcat Chukka Boot (Women's)
Franco Sarto Tomcat Chukka Boot (Women's)
Franco Sarto Tomcat Chukka Boot (Women's)
New!
Sale
Franco Sarto Tomcat Chukka Boot(
                                      Women's) -
                                     Anthracite Matte Metallic Leather
Sale
Franco Sarto Tomcat Chukka Boot(
                                      Women's) -
                                     Black Sofia Crust Leather
Sale
Franco Sarto Tomcat Chukka Boot(
                                      Women's) -
                                     Bronze Matte Metallic Leather
Sale
Franco Sarto Tomcat Chukka Boot(
                                      Women's) -
                                     Dark Blue Box Leather
Sale
$97.95
$139.00 30% 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
$174.95 - $229.95
$230.00 up to 24% off
Dr. Martens Daytona Chukka Boot (Women's)
Dr. Martens Daytona Chukka Boot (Women's)
New!
Sale
Dr. Martens Daytona Chukka Boot(
                                      Women's) -
                                     Lead Overdyed Twill Canvas
Sale
$49.95 - $74.95
$70.00 - $75.00 up to 33% off
Dockers Tussock (Men's)
Dockers Tussock (Men's)
Dockers Tussock (Men's)
New!
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
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
Dr. Martens Jayda Desert Boot (Women's)
Dr. Martens Jayda Desert Boot (Women's)
New!
Sale
Dr. Martens Jayda Desert Boot(
                                      Women's) -
                                     Grey/Black Tweed
Sale
$79.95
$110.00 27% 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
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
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
Boston Boot Co. Commonwealth Boot (Men's)
Boston Boot Co. Commonwealth Boot (Men's)
Boston Boot Co. Commonwealth Boot (Men's)
Boston Boot Co. Commonwealth Boot (Men's)
New!
Sale
Boston Boot Co. Commonwealth Boot(
                                      Men's) -
                                     Black Leather
Sale
Boston Boot Co. Commonwealth Boot(
                                      Men's) -
                                     Brown/Nicotine Leather
Sale
Boston Boot Co. Commonwealth Boot(
                                      Men's) -
                                     Natural/White Leather
Sale
$144.95
$207.00 30% off
Clarks Fulham Hi (Men's)
Clarks Fulham Hi (Men's)
New!
Sale
Clarks Fulham Hi(
                                      Men's) -
                                     Brown Leather
Sale
$51.95
$125.00 58% 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)
New!
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
$79.99 - $127.95
$128.00 up to 38% off
Rockport Rugged Bucks Waterproof Boot (Men's)
Rockport Rugged Bucks Waterproof Boot (Men's)
New!
Sale
Rockport Rugged Bucks Waterproof Boot(
                                      Men's) -
                                     Tan Full Grain Leather
Sale
$109.95 - $119.95
$120.00 up to 8% off
Lugz Chukka Ballistic (Men's)
Lugz Chukka Ballistic (Men's)
New!
Sale
Lugz Chukka Ballistic(
                                      Men's) -
                                     Wheat/Cream Ballistic Nylon
Sale
$39.95
$64.99 39% off
Lugz Cargo Ankle Boot (Men's)
Lugz Cargo Ankle Boot (Men's)
Lugz Cargo Ankle Boot (Men's)
New!
Sale
Lugz Cargo Ankle Boot(
                                      Men's) -
                                     Black Permahide
Sale
Lugz Cargo Ankle Boot(
                                      Men's) -
                                     Black/Charcoal Durabrush
Sale
$49.95
$69.99 29% off
Boston Boot Co. Newbury Chukka Boot (Men's)
Boston Boot Co. Newbury Chukka Boot (Men's)
Boston Boot Co. Newbury Chukka Boot (Men's)
New!
Sale
Boston Boot Co. Newbury Chukka Boot(
                                      Men's) -
                                     Black Leather
Sale
Boston Boot Co. Newbury Chukka Boot(
                                      Men's) -
                                     Natural Leather
Sale
$151.95
$217.00 30% off
Marc New York by Andrew Marc Stanton (Men's)
Marc New York by Andrew Marc Stanton (Men's)
New!
Sale
Marc New York by Andrew Marc Stanton(
                                      Men's) -
                                     Olive/Catfish/Nude/Gum Canvas
Sale
$59.99
$128.00 53% off
Lugz Rickshaw (Men's)
Lugz Rickshaw (Men's)
Lugz Rickshaw (Men's)
Lugz Rickshaw (Men's)
Lugz Rickshaw (Men's)
New!
Sale
Lugz Rickshaw(
                                      Men's) -
                                     Black Permahide
Sale
Lugz Rickshaw(
                                      Men's) -
                                     Black/Gum Synthetic Suede
Sale
Lugz Rickshaw(
                                      Men's) -
                                     Dark Mahogany/Gum Permahide
Sale
Lugz Rickshaw(
                                      Men's) -
                                     Sand/Gum Synthetic Suede
Sale
$49.95
$49.95 - $69.99 up to 29% off
Related Products
Famous for its clean lines, simple construction and classic round toe styling, the Roughneck Round Toe Boot features a leather ...
This military boot has a water resistant leather and Cordura® nylon upper with a PTFE flame resistant coating, 400 grams ...
Electrify your distinctive style with the Mark Nason SKECHERS Copperstown boot. Smooth oiled leather and distressed suede upper in a ...