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

Mens Chukka Boots

1-36 of 221 results
 1 2 3 4 5 
Sort by
Display
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) -
                                     Amber Gold
Clarks Desert Boot(
                                      Men's) -
                                     Beeswax
Clarks Desert Boot(
                                      Men's) -
                                     Black Suede
Sale
Clarks Desert Boot(
                                      Men's) -
                                     Black Smooth
Clarks Desert Boot(
                                      Men's) -
                                     Brown
Clarks Desert Boot(
                                      Men's) -
                                     Green Leather
Clarks Desert Boot(
                                      Men's) -
                                     Leaf Suede
Clarks Desert Boot(
                                      Men's) -
                                     New Black Suede
Clarks Desert Boot(
                                      Men's) -
                                     New Sand Suede
Clarks Desert Boot(
                                      Men's) -
                                     Rust Leather
Clarks Desert Boot(
                                      Men's) -
                                     Sand SixtyFive Suede
Clarks Desert Boot(
                                      Men's) -
                                     Taupe Distressed Suede
Clarks Desert Boot(
                                      Men's) -
                                     Terracotta Suede
$109.95 - $399.95
$130.00 - $400.00 up to 15% 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)
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
$149.95
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)
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 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) -
                                     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/Brown Suede
Clarks Wallabee Boot(
                                      Men's) -
                                     Brown Tumbled Leather
Clarks Wallabee Boot(
                                      Men's) -
                                     Dark Brown Suede
Clarks Wallabee Boot(
                                      Men's) -
                                     Leaf Leather
Clarks Wallabee Boot(
                                      Men's) -
                                     Maple Suede
Clarks Wallabee Boot(
                                      Men's) -
                                     Rust Leather
$139.95
ECCO Turn GORE-TEX Boot (Men's)
ECCO Turn GORE-TEX Boot (Men's)
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 Lexi Leather
ECCO Turn GORE-TEX Boot(
                                      Men's) -
                                     Black Oil Nubuck
Sale
ECCO Turn GORE-TEX Boot(
                                      Men's) -
                                     Mocha Oil Nubuck
Sale
ECCO Turn GORE-TEX Boot(
                                      Men's) -
                                     Coffee Lexi Leather
$174.95 - $229.95
$230.00 up to 24% 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
UGG Galen Chukka Boot (Men's)
UGG Galen Chukka Boot (Men's)
UGG Galen Chukka Boot (Men's)
New!
Sale
UGG Galen Chukka Boot(
                                      Men's) -
                                     Black Leather
UGG Galen Chukka Boot(
                                      Men's) -
                                     Espresso Leather
$194.95
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)
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)
Rockport Charson Lace Up Ankle Boot (Men's)
New!
Sale
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
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 RocSports Lite 2 Chukka Boot (Men's)
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) -
                                     Tan Leather
Rockport RocSports Lite 2 Chukka Boot(
                                      Men's) -
                                     Taupe Nubuck
Sale
$109.95
$120.00 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
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 Casey Chukka Boot (Men's)
Florsheim Casey Chukka Boot (Men's)
Florsheim Casey Chukka Boot (Men's)
Florsheim Casey Chukka Boot (Men's)
New!
Sale
Florsheim Casey Chukka Boot(
                                      Men's) -
                                     Black Leather
Florsheim Casey Chukka Boot(
                                      Men's) -
                                     Brown Leather
Florsheim Casey Chukka Boot(
                                      Men's) -
                                     Cognac Leather
$119.95
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) -
                                     Tan Leather
Sale
$89.95
$100.00 10% 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
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
Steve Madden Hestonn (Men's)
Steve Madden Hestonn (Men's)
Steve Madden Hestonn (Men's)
Steve Madden Hestonn (Men's)
New!
Sale
Steve Madden Hestonn(
                                      Men's) -
                                     Dark Brown Leather
Steve Madden Hestonn(
                                      Men's) -
                                     Grey Leather
Steve Madden Hestonn(
                                      Men's) -
                                     Tan Leather
$84.95
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  Leather
Steve Madden Harken Chukka(
                                      Men's) -
                                     Cognac Leather
$84.95 - $89.95
Stacy Adams Tiptop Chukka Boot 53418 (Men's)
Stacy Adams Tiptop Chukka Boot 53418 (Men's)
Stacy Adams Tiptop Chukka Boot 53418 (Men's)
Stacy Adams Tiptop Chukka Boot 53418 (Men's)
Stacy Adams Tiptop Chukka Boot 53418 (Men's)
New!
Sale
Stacy Adams Tiptop Chukka Boot 53418(
                                      Men's) -
                                     Black PU
Stacy Adams Tiptop Chukka Boot 53418(
                                      Men's) -
                                     Cognac PU
Stacy Adams Tiptop Chukka Boot 53418(
                                      Men's) -
                                     Navy PU
Stacy Adams Tiptop Chukka Boot 53418(
                                      Men's) -
                                     Red PU
$74.95
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) -
                                     Gray Suede
Naot Pilot(
                                      Men's) -
                                     Seal Brown Suede
Naot Pilot(
                                      Men's) -
                                     Vintage Grey Leather
$199.95
Clarks Hawkley Rise Chukka (Men's)
Clarks Hawkley Rise Chukka (Men's)
Clarks Hawkley Rise Chukka (Men's)
New!
Sale
Clarks Hawkley Rise Chukka(
                                      Men's) -
                                     Dark Brown Combi
New
Clarks Hawkley Rise Chukka(
                                      Men's) -
                                     Tan Leather
New
$124.95