Order Anytime, Free Shipping, Free Returns

“chukka and Boots” we found 181 items!

Choose a
  • Product Type
to sort results

We adjusted your search results to be more relevant. Not what you were looking for? Click here.

Robert Wayne - Brent Robert Wayne Brent $45.00 Rated: 4 stars! Robert Wayne - Brent Robert Wayne Brent $45.00 Rated: 4 stars! Deer Stags - Mean Deer Stags Mean $60.00 Rated: 4 stars! Nunn Bush - Dodge Wing Tip Chukka Boot Nunn Bush Dodge Wing Tip Chukka Boot $64.00 Rated: 4 stars!
Nunn Bush - Dodge Wing Tip Chukka Boot Nunn Bush Dodge Wing Tip Chukka Boot $64.00 Rated: 4 stars! Nunn Bush - Dodge Wing Tip Chukka Boot Nunn Bush Dodge Wing Tip Chukka Boot $68.00 Rated: 4 stars! Nunn Bush - Dodge Wing Tip Chukka Boot Nunn Bush Dodge Wing Tip Chukka Boot $68.00 Rated: 4 stars! Dr. Martens - Mayport 2-Eye Desert Boot Dr. Martens Mayport 2-Eye Desert Boot $70.00 Rated: 5 stars!
Dr. Martens - Mayport 2-Eye Desert Boot Dr. Martens Mayport 2-Eye Desert Boot $70.00 Rated: 5 stars! Dr. Martens - Mayport 2-Eye Desert Boot Dr. Martens Mayport 2-Eye Desert Boot $70.00 Rated: 5 stars! Dr. Martens - Daytona Dr. Martens Daytona $70.00 Rated: 4 stars! Dr. Martens - Cabrillo Dr. Martens Cabrillo $80.00 Rated: 5 stars!
Dr. Martens - Cabrillo Dr. Martens Cabrillo $80.00 Rated: 5 stars! Deer Stags - Somers Deer Stags Somers $80.00 Deer Stags - Somers Deer Stags Somers $80.00 Deer Stags - Mean Deer Stags Mean $80.00 Rated: 4 stars!
Deer Stags - Bristol Deer Stags Bristol $80.00 Deer Stags - Bristol Deer Stags Bristol $80.00 Steve Madden - Harken Steve Madden Harken $85.00 Rated: 4 stars! Trotters - Snowflakes III Trotters Snowflakes III $89.00 Rated: 4 stars!
Lucky Brand - Garboh Lucky Brand Garboh $89.00 Rated: 4 stars! Steve Madden - Henrie1 (Extended Sizes) Steve Madden Henrie1 (Extended Sizes) $90.00 Rated: 5 stars! Mark Nason - Lansing Mark Nason Lansing $90.00 Rated: 5 stars! Nunn Bush - Hawley Plain Toe Chukka Nunn Bush Hawley Plain Toe Chukka $90.00 Rated: 4 stars!
Kenneth Cole Reaction - Desert Sun Kenneth Cole Reaction Desert Sun $98.00 Hush Puppies - Cyra Catelyn Hush Puppies Cyra Catelyn $99.00 Rated: 5 stars! Hush Puppies - Cyra Catelyn Hush Puppies Cyra Catelyn $99.00 Rated: 5 stars! Hush Puppies - Cyra Catelyn Hush Puppies Cyra Catelyn $99.00 Rated: 5 stars!
Hush Puppies - Cyra Catelyn Hush Puppies Cyra Catelyn $99.00 Rated: 5 stars! Hush Puppies - Cyra Catelyn Hush Puppies Cyra Catelyn $99.00 Rated: 5 stars! Hush Puppies - Cyra Catelyn Hush Puppies Cyra Catelyn $99.00 Rated: 5 stars! NEW! Robert Wayne - Roma Robert Wayne Roma $99.95 Rated: 4 stars!
Mark Nason - Stroud Mark Nason Stroud $100.00 Giorgio Brutini - Thorton Giorgio Brutini Thorton $109.00 Giorgio Brutini - Thorton Giorgio Brutini Thorton $109.00 Robert Wayne - Tatum Robert Wayne Tatum $109.95
Robert Wayne - Tatum Robert Wayne Tatum $109.95 Born - Harrison Born Harrison $110.00 Rated: 4 stars! Born - Harrison Born Harrison $110.00 Rated: 4 stars! Born - Twain Born Twain $119.00 Rated: 4 stars!
Born - Twain Born Twain $119.00 Rated: 4 stars! Roper - Performance 2-Eyelet Ankle Boot Roper Performance 2-Eyelet Ankle Boot $120.00 Rated: 4 stars! Roper - Siped Outsole Performance Ankle Boot Roper Siped Outsole Performance Ankle Boot $120.00 Rated: 5 stars! Roper - Siped Outsole Performance Ankle Boot Roper Siped Outsole Performance Ankle Boot $120.00 Rated: 5 stars!
Florsheim - Casey Chukka Boot Florsheim Casey Chukka Boot $120.00 Rated: 4 stars! Florsheim - Casey Chukka Boot Florsheim Casey Chukka Boot $120.00 Rated: 4 stars! Florsheim - Casey Chukka Boot Florsheim Casey Chukka Boot $120.00 Rated: 4 stars! Mark Nason - Elmwood Mark Nason Elmwood $120.00 Rated: 1 stars!
Roper - Performance 2-Eyelet Ankle Boot Roper Performance 2-Eyelet Ankle Boot $125.00 Rated: 4 stars! The North Face - Ballard II Chukka The North Face Ballard II Chukka $130.00 Rated: 4 stars! The North Face - Ballard II Chukka The North Face Ballard II Chukka $130.00 Rated: 4 stars! Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars!
Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! Calvin Klein - Ballard Calvin Klein Ballard $130.00 Rated: 5 stars! Born - Twain Born Twain $130.00 Rated: 4 stars! NEW!
Florsheim - Rockit Chukka Boot Florsheim Rockit Chukka Boot $135.00 Rated: 4 stars! Florsheim - Rockit Chukka Boot Florsheim Rockit Chukka Boot $135.00 Rated: 4 stars! Hush Puppies - Style Chukka PL Hush Puppies Style Chukka PL $139.00 Rated: 4 stars! Hush Puppies - Style Chukka PL Hush Puppies Style Chukka PL $139.00 Rated: 4 stars!
Polo Ralph Lauren - Torrington Chukka Polo Ralph Lauren Torrington Chukka $139.00 Rated: 5 stars! LAUREN by Ralph Lauren - Malva LAUREN by Ralph Lauren Malva $139.00 Rated: 3 stars! Timberland - Earthkeepers® Stormbuck Duck Chukka Timberland Earthkeepers® Stormbuck Duck Chukka $140.00 Rated: 4 stars! Clarks - Montacute Duke Clarks Montacute Duke $140.00 Rated: 4 stars!
Dr. Martens - Sawyer Desert Boot Dr. Martens Sawyer Desert Boot $140.00 Rated: 5 stars! Dr. Martens - Sawyer Desert Boot Dr. Martens Sawyer Desert Boot $140.00 Rated: 5 stars! Steve Madden - Beckon Steve Madden Beckon $140.00 Rated: 5 stars! Steve Madden - Beckon Steve Madden Beckon $140.00 Rated: 5 stars!
Johnston & Murphy - Copeland Chukka Johnston & Murphy Copeland Chukka $145.00 Rated: 5 stars! Dunham - Johnson Chukka Dunham Johnson Chukka $145.00 Rockport - Ledge Hill 2 Chukka Boot Rockport Ledge Hill 2 Chukka Boot $149.95 Rated: 4 stars! Rockport - Ledge Hill 2 Chukka Boot Rockport Ledge Hill 2 Chukka Boot $149.95 Rated: 4 stars!
Rockport - Ledge Hill 2 Chukka Boot Rockport Ledge Hill 2 Chukka Boot $150.00 Rated: 4 stars! Bogs - Kristina Chukka Bogs Kristina Chukka $150.00 Rated: 5 stars! Bogs - Kristina Chukka Bogs Kristina Chukka $150.00 Rated: 5 stars! Bogs - Kristina Chukka Bogs Kristina Chukka $150.00 Rated: 5 stars!
Johnston & Murphy - Copeland Chukka Johnston & Murphy Copeland Chukka $150.00 Rated: 5 stars! Johnston & Murphy - Copeland Chukka Johnston & Murphy Copeland Chukka $150.00 Rated: 5 stars! Bogs - Johnny Chukka Bogs Johnny Chukka $155.00 Rated: 4 stars! Bogs - Johnny Chukka Bogs Johnny Chukka $155.00 Rated: 4 stars!
Bogs - Johnny Chukka Bogs Johnny Chukka $155.00 Rated: 4 stars! Dune London - Montenegro Dune London Montenegro $159.00 Rated: 4 stars! Rockport - City Smart - Waterproof Dress Chukka Boot Rockport City Smart - Waterproof Dress Chukka Boot $159.95 Rated: 3 stars! Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $160.00 Rated: 5 stars!
Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $160.00 Rated: 5 stars! Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $160.00 Rated: 5 stars! Merrell - Veranda Lace Merrell Veranda Lace $160.00 Rated: 4 stars! Merrell - Veranda Lace Merrell Veranda Lace $160.00 Rated: 4 stars!
Merrell - Veranda Lace Merrell Veranda Lace $160.00 Rated: 4 stars! Timberland - West Haven Chukka Timberland West Haven Chukka $160.00 Rated: 5 stars! Timberland - West Haven Chukka Timberland West Haven Chukka $160.00 Rated: 5 stars! Geox - Uomo Claudio 15 Geox Uomo Claudio 15 $165.00
Geox - Uomo Claudio 15 Geox Uomo Claudio 15 $165.00 Geox - Uomo Claudio 15 Geox Uomo Claudio 15 $165.00 SeaVees - 12/67 3 Eye Chukka SeaVees 12/67 3 Eye Chukka $168.00 Rated: 4 stars! Massimo Matteo - 3-Eye Chukka Massimo Matteo 3-Eye Chukka $169.00 Rated: 5 stars!
Massimo Matteo - 3-Eye Chukka Boot Massimo Matteo 3-Eye Chukka Boot $169.00 Harley-Davidson - Beau Harley-Davidson Beau $174.00 Wolverine - Francisco Chukka Wolverine Francisco Chukka $175.00 Rated: 5 stars! Wolverine - Francisco Chukka Wolverine Francisco Chukka $175.00 Rated: 5 stars!

Need Help?

Customer Service Representative

Have size or selection questions? We can help!

Begin Live Chat
Close
Zappos Family Core Value:

10. Be Humble