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Discount Chukka Boots

1-36 of 68 results
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Clarks Desert Boot (Men's)
Clarks Desert Boot (Men's)
New!
Sale
Clarks Desert Boot(
                                      Men's) -
                                     Black Suede
Sale
$109.95 - $399.95
$130.00 - $400.00 up to 15% 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
Red Wing Handsewn Chukka (Men's)
Red Wing Handsewn Chukka (Men's)
Red Wing Handsewn Chukka (Men's)
New!
Sale
Red Wing Handsewn Chukka(
                                      Men's) -
                                     Amber Harness Leather
Sale
Red Wing Handsewn Chukka(
                                      Men's) -
                                     Charcoal Rough And Tough
Sale
$108.95 - $155.95
$310.00 up to 65% off
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) -
                                     Black Oil Nubuck
Sale
ECCO Turn GORE-TEX Boot(
                                      Men's) -
                                     Mocha Oil Nubuck
Sale
$174.95 - $229.95
$230.00 up to 24% off
Clarks Senner Drive (Men's)
Clarks Senner Drive (Men's)
New!
Sale
Clarks Senner Drive(
                                      Men's) -
                                     Chocolate Nubuck
Sale
$67.45
$100.00 33% 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)
New!
Sale
Rockport Rugged Bucks Waterproof Boot(
                                      Men's) -
                                     Espresso Nubuck
Sale
Rockport Rugged Bucks Waterproof Boot(
                                      Men's) -
                                     Tan Full Grain Leather
Sale
Rockport Rugged Bucks Waterproof Boot(
                                      Men's) -
                                     Wheat Nubuck
Sale
$109.95
$120.00 8% 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
Rockport RocSports Lite 2 Chukka Boot (Men's)
Rockport RocSports Lite 2 Chukka Boot (Men's)
Rockport RocSports Lite 2 Chukka Boot (Men's)
New!
Sale
Rockport RocSports Lite 2 Chukka Boot(
                                      Men's) -
                                     Brown Leather
Sale
Rockport RocSports Lite 2 Chukka Boot(
                                      Men's) -
                                     Taupe Nubuck
Sale
$90.95 - $109.95
$120.00 up to 24% 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
$165.95
$207.00 20% off
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) -
                                     Charcoal Grey Suede
Sale
Clarks Stinson Hi(
                                      Men's) -
                                     Chocolate Brown Suede
Sale
Clarks Stinson Hi(
                                      Men's) -
                                     Navy Cow Suede
Sale
$71.45 - $99.95
$100.00 up to 29% off
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) -
                                     Tan Leather
Sale
$89.95
$100.00 10% off
Boston Boot Co. Cambridge Chukka Boot (Men's)
Boston Boot Co. Cambridge Chukka Boot (Men's)
Boston Boot Co. Cambridge Chukka Boot (Men's)
Boston Boot Co. Cambridge Chukka Boot (Men's)
New!
Sale
Boston Boot Co. Cambridge Chukka Boot(
                                      Men's) -
                                     Brown Canvas
Sale
Boston Boot Co. Cambridge Chukka Boot(
                                      Men's) -
                                     Brown Leather
Sale
Boston Boot Co. Cambridge Chukka Boot(
                                      Men's) -
                                     Natural Canvas
Sale
$157.95
$197.00 20% 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
Florsheim Rockit Chukka (Men's)
Florsheim Rockit Chukka (Men's)
Florsheim Rockit Chukka (Men's)
New!
Sale
Florsheim Rockit Chukka(
                                      Men's) -
                                     Black Distressed Milled Leather
Sale
Florsheim Rockit Chukka(
                                      Men's) -
                                     Brown Distressed Milled Leather
Sale
$101.95
$135.00 24% off
Aerosoles Landlock (Women's)
Aerosoles Landlock (Women's)
Aerosoles Landlock (Women's)
Aerosoles Landlock (Women's)
Aerosoles Landlock (Women's)
New!
Sale
Aerosoles Landlock(
                                      Women's) -
                                     Black Leather
Sale
Aerosoles Landlock(
                                      Women's) -
                                     Black Suede
Sale
Aerosoles Landlock(
                                      Women's) -
                                     Dark Blue Suede
Sale
Aerosoles Landlock(
                                      Women's) -
                                     Taupe Suede
Sale
$49.99
$89.00 44% 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
$68.00
$75.00 9% 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
Timberland Classic TBLŪ Chukka (Men's)
Timberland Classic TBLŪ Chukka (Men's)
New!
Sale
Timberland Classic TBLŪ Chukka(
                                      Men's) -
                                     Black Smooth Leather
Sale
$119.95 - $134.95
$135.00 up to 11% off
Mark Nason Skechers Elmwood (Men's)
Mark Nason Skechers Elmwood (Men's)
New!
Sale
Mark Nason Skechers Elmwood(
                                      Men's) -
                                     Black
Sale
$99.95
$124.00 19% off
Bed Stu Draco Chukka Boot (Men's)
Bed Stu Draco Chukka Boot (Men's)
New!
Sale
Bed Stu Draco Chukka Boot(
                                      Men's) -
                                     Black Handwash Leather
Sale
$116.95 - $134.95
$155.00 up to 25% 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
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
$173.95
$217.00 20% off
Tommy Hilfiger Sten Chukka (Men's)
Tommy Hilfiger Sten Chukka (Men's)
Tommy Hilfiger Sten Chukka (Men's)
New!
Sale
Tommy Hilfiger Sten Chukka(
                                      Men's) -
                                     Navy Suede/Coffee Bean Pu
Sale
Tommy Hilfiger Sten Chukka(
                                      Men's) -
                                     Taupe Suede/Coffee Bean Pu
Sale
$84.95
$130.00 35% 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
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) -
                                     Caribou/Black/Dark Natural/Natural Suede
Sale
Andrew Marc Dorchester Chukka(
                                      Men's) -
                                     Dark Brown/Black/Dark Natural/Natural Suede
Sale
Andrew Marc Dorchester Chukka(
                                      Men's) -
                                     Tobacco/Black/Deep Natural Suede
Sale
$133.50 - $164.95
$177.99 - $178.00 up to 25% off
Born Hamids Chukka Boot (Women's)
Born Hamids Chukka Boot (Women's)
Born Hamids Chukka Boot (Women's)
Born Hamids Chukka Boot (Women's)
New!
Sale
Born Hamids Chukka Boot(
                                      Women's) -
                                     Black Full Grain Leather
Sale
Born Hamids Chukka Boot(
                                      Women's) -
                                     Cafe Full Grain Leather
Sale
Born Hamids Chukka Boot(
                                      Women's) -
                                     Tierra Full Grain Leather
Sale
$98.95
$129.00 23% off
Tsubo Beale (Men's)
Tsubo Beale (Men's)
New!
Sale
Tsubo Beale(
                                      Men's) -
                                     Dark Chocolate Suede
Sale
$52.95 - $149.95
$150.00 up to 65% off
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) -
                                     Sand Overdyed Twill Canvas
Sale
$52.95 - $69.95
$70.00 up to 24% 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
Merrell Ashland Chukka (Women's)
Merrell Ashland Chukka (Women's)
Merrell Ashland Chukka (Women's)
Merrell Ashland Chukka (Women's)
New!
Sale
Merrell Ashland Chukka(
                                      Women's) -
                                     Black
Sale
Merrell Ashland Chukka(
                                      Women's) -
                                     Brown Sugar
Sale
Merrell Ashland Chukka(
                                      Women's) -
                                     Bungee Cord
Sale
$116.95
$130.00 10% off
Born Asten (Men's)
Born Asten (Men's)
Born Asten (Men's)
New!
Sale
Born Asten(
                                      Men's) -
                                     Bark Leather
Sale
Born Asten(
                                      Men's) -
                                     Sabbia Suede
Sale
$94.95 - $99.95
$105.00 - $115.00 up to 13% 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)
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
White Mountain Irma Wedge Heel Bootie(
                                      Women's) -
                                     Taupe Suede
Sale
$46.95
$79.00 41% off
Camper Morrys Chukka Boot (Men's)
Camper Morrys Chukka Boot (Men's)
Camper Morrys Chukka Boot (Men's)
New!
Sale
Camper Morrys Chukka Boot(
                                      Men's) -
                                     Dark Green Nubuck
Sale
Camper Morrys Chukka Boot(
                                      Men's) -
                                     Medium Brown Leather
Sale
$149.95
$199.00 25% off
The North Face Ballard II Chukka Boot (Men's)
The North Face Ballard II Chukka Boot (Men's)
New!
Sale
The North Face Ballard II Chukka Boot(
                                      Men's) -
                                     Chutney Brown/Cherry Stain Brown
Sale
$84.95
$130.00 35% off
Frye Jim Chukka Boot (Men's)
Frye Jim Chukka Boot (Men's)
Frye Jim Chukka Boot (Men's)
New!
Sale
Frye Jim Chukka Boot(
                                      Men's) -
                                     Black Leather
Sale
Frye Jim Chukka Boot(
                                      Men's) -
                                     Cognac Leather
Sale
$213.95
$268.00 20% 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
$74.99 - $94.95
$90.00 up to 17% off