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 235 results
 1 2 3 4 5 
Sort by
Display
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 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 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) -
                                     Navy Leather
Clarks Desert Boot(
                                      Men's) -
                                     New Black Suede
Clarks Desert Boot(
                                      Men's) -
                                     Rust Leather
Clarks Desert Boot(
                                      Men's) -
                                     Sand Somerset
Clarks Desert Boot(
                                      Men's) -
                                     Taupe Distressed Suede
Clarks Desert Boot(
                                      Men's) -
                                     Terracotta Suede
Clarks Desert Boot(
                                      Men's) -
                                     White Leather
$129.95
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)
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
Clarks Bushacre 2(
                                      Men's) -
                                     Wheat Suede
$73.95 - $99.95
$100.00 up to 26% off
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
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) -
                                     Beeswax/Beeswax Leather
Clarks Wallabee(
                                      Men's) -
                                     Black/Black Leather
Clarks Wallabee(
                                      Men's) -
                                     Brown Tumbled Leather
Clarks Wallabee(
                                      Men's) -
                                     Maple Suede
Clarks Wallabee(
                                      Men's) -
                                     Off White Suede
$134.95
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
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 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
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
UGG Freamon Chukka Boot (Men's)
UGG Freamon Chukka Boot (Men's)
UGG Freamon Chukka Boot (Men's)
UGG Freamon Chukka Boot (Men's)
UGG Freamon Chukka Boot (Men's)
New!
Sale
UGG Freamon Chukka Boot(
                                      Men's) -
                                     Black Suede
UGG Freamon Chukka Boot(
                                      Men's) -
                                     Chestnut/White
UGG Freamon Chukka Boot(
                                      Men's) -
                                     New Navy Suede
UGG Freamon Chukka Boot(
                                      Men's) -
                                     Seal Suede
$109.95
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) -
                                     Dark Brown Suede
Clarks Wallabee Boot(
                                      Men's) -
                                     Maple Suede
Clarks Wallabee Boot(
                                      Men's) -
                                     Rust Leather
$127.95 - $139.95
$140.00 up to 9% 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
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
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
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 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
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
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
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
Stacy Adams Astro 53404 (Men's)
New!
Sale
Stacy Adams Astro 53404(
                                      Men's) -
                                     Black Smooth Leather
Sale
Stacy Adams Astro 53404(
                                      Men's) -
                                     Black Suede
Stacy Adams Astro 53404(
                                      Men's) -
                                     Brown Suede
Sale
Stacy Adams Astro 53404(
                                      Men's) -
                                     Gray Suede
Sale
Stacy Adams Astro 53404(
                                      Men's) -
                                     Sand Suede
$62.95 - $89.95
$90.00 up to 30% off
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
Rockport Ledge Hill Too Chukka Boot (Men's)
Rockport Ledge Hill Too Chukka Boot (Men's)
Rockport Ledge Hill Too Chukka Boot (Men's)
Rockport Ledge Hill Too Chukka Boot (Men's)
Rockport Ledge Hill Too Chukka Boot (Men's)
New!
Sale
Rockport Ledge Hill Too Chukka Boot(
                                      Men's) -
                                     Black Leather
Rockport Ledge Hill Too Chukka Boot(
                                      Men's) -
                                     Castlerock Suede
Rockport Ledge Hill Too Chukka Boot(
                                      Men's) -
                                     Dark Brown Leather
Rockport Ledge Hill Too Chukka Boot(
                                      Men's) -
                                     Peacock Leather
$149.95
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
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
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
Timberland Amherst Chukka Boot (Men's)
Timberland Amherst Chukka Boot (Men's)
Timberland Amherst Chukka Boot (Men's)
Timberland Amherst Chukka Boot (Men's)
New!
Sale
Timberland Amherst Chukka Boot(
                                      Men's) -
                                     Brown Canvas
Timberland Amherst Chukka Boot(
                                      Men's) -
                                     Navy Canvas
Timberland Amherst Chukka Boot(
                                      Men's) -
                                     Teak Canvas
$99.95
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) -
                                     Peanut Leather
Eastland Seneca(
                                      Men's) -
                                     Tan Waxee Leather
$99.95 - $109.95
Drew Keith (Men's)
Drew Keith (Men's)
Drew Keith (Men's)
New!
Sale
Drew Keith(
                                      Men's) -
                                     Black Leather
Drew Keith(
                                      Men's) -
                                     Brandy Leather
$189.95
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