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 115 results
 1 2 3 4 
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)
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
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) -
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
$129.95
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
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 (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) -
Navy Leather
Sale
Clarks Bushacre 2(
Men's) -
Tan Leather
Sale
Clarks Bushacre 2(
Men's) -
Wheat Suede
$89.95 - $99.95
$100.00 up to 10% 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)
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
Florsheim NDNS Chukka Boot (Men's)
Florsheim NDNS Chukka Boot (Men's)
Florsheim NDNS Chukka Boot (Men's)
New!
Sale
Florsheim NDNS Chukka Boot(
Men's) -
Brown Nubuck Leather
New
Florsheim NDNS Chukka Boot(
Men's) -
Black Leather
$129.95
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
Rockport Rugged Bucks Waterproof Boot(
Men's) -
Tan Full Grain Leather
Sale
Rockport Rugged Bucks Waterproof Boot(
Men's) -
Wheat Nubuck
$109.95 - $119.95
$120.00 up to 8% off
Dr. Martens Barnie Chukka Boot (Men's)
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) -
Black Overdrive
Dr. Martens Barnie Chukka Boot(
Men's) -
Dark Brown Grizzly
Sale
$89.95 - $119.95
$120.00 up to 25% 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
Sale
Steve Madden Hestonn(
Men's) -
Grey Leather
Sale
Steve Madden Hestonn(
Men's) -
Tan Leather
Sale
$65.95 - $84.95
$90.00 up to 27% 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 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)
New!
Sale
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
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
$174.95 - $229.95
$230.00 up to 24% 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
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)
New!
Sale
Clarks Stinson Lo(
Men's) -
Beeswax Leather
Sale
$89.95
$100.00 10% off
Dr. Martens Izzy Steel Toe 3 Eye Chukka (Women's)
Dr. Martens Izzy Steel Toe 3 Eye Chukka (Women's)
Dr. Martens Izzy Steel Toe 3 Eye Chukka (Women's)
New!
Sale
Dr. Martens Izzy Steel Toe 3 Eye Chukka(
Women's) -
Black Industrial Bear
Sale
Dr. Martens Izzy Steel Toe 3 Eye Chukka(
Women's) -
Teak Industrial Bear
$110.45 - $124.95
$125.00 up to 12% 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
Timberland Britton Hill Waterproof Chukka Boot (Men's)
Timberland Britton Hill Waterproof Chukka Boot (Men's)
Timberland Britton Hill Waterproof Chukka Boot (Men's)
New!
Sale
Timberland Britton Hill Waterproof Chukka Boot(
Men's) -
Black Quartz with Buttersoft
Sale
Timberland Britton Hill Waterproof Chukka Boot(
Men's) -
Chestnut Quartz with Buttersoft
Sale
$140.95
$180.00 22% 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
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
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
Twisted X Boots MDMS003 (Men's)
Twisted X Boots MDMS003 (Men's)
New!
Sale
Twisted X Boots MDMS003(
Men's) -
Dusty Tan Leather
Sale
$60.49
$104.99 42% off
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
Merrell All Out Blazer Chukka (Men's)
Merrell All Out Blazer Chukka (Men's)
Merrell All Out Blazer Chukka (Men's)
Merrell All Out Blazer Chukka (Men's)
Merrell All Out Blazer Chukka (Men's)
New!
Sale
Merrell All Out Blazer Chukka(
Men's) -
Pewter
New
Merrell All Out Blazer Chukka(
Men's) -
Black
Merrell All Out Blazer Chukka(
Men's) -
Clay
Merrell All Out Blazer Chukka(
Men's) -
Merrell Tan
$129.95
Related Products
The Ruffout Chukka M features a soft glove leather collar lining, microfiber footbed lining, die-cut OM Foam midsole, and a ...
Put some style fizz into your look with the Mark Nason SKECHERS Tonic boot. Smooth premium leather upper in a ...
The slim, fashion-forward chukka silhouette of the Galen satisfies the dapper gentleman's need for smart design and comfort. This 3 ...