No Way! Free Next Day Shipping On Clothing M-F. Order Today, Wear It Tomorrow! Plus Free Returns. Learn More

“chukka and Men Boots” we found 114 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.

Polo Ralph Lauren - Torrington Chukka Polo Ralph Lauren Torrington Chukka $139.00 Bed Stu - Draco Bed Stu Draco $135.00 Rated: 5 stars! Steve Madden - Eastsyde Steve Madden Eastsyde $75.00 ECCO - Findlay Chukka Boot ECCO Findlay Chukka Boot $210.00
Steve Madden - Harken Steve Madden Harken $85.00 Rated: 4 stars! Type Z - Eliott Type Z Eliott $129.00 Rated: 3 stars! Steve Madden - Garisonn Steve Madden Garisonn $110.00 Born - Twain Born Twain $119.00 Rated: 4 stars!
John Varvatos - Hipster Chukka John Varvatos Hipster Chukka $198.00 Rated: 4 stars! Frye - Walter Chukka Frye Walter Chukka $348.00 Rated: 5 stars! Nunn Bush - Dodge Nunn Bush Dodge $85.00 Robert Wayne - Roma Robert Wayne Roma $89.95 Rated: 4 stars!
Calvin Klein - Ulysses Calvin Klein Ulysses $140.00 Kenneth Cole Reaction - Real Deal Kenneth Cole Reaction Real Deal $88.00 Rated: 5 stars! Frye - Oliver Chukka Frye Oliver Chukka $258.00 Rated: 4 stars! ECCO - Findlay Chukka Boot ECCO Findlay Chukka Boot $210.00
Rockport - Ledge Hill 2 Chukka Boot Rockport Ledge Hill 2 Chukka Boot $150.00 Salvatore Ferragamo - Pioneer Ankle Boot Salvatore Ferragamo Pioneer Ankle Boot $595.00 Steve Madden - Garisonn Steve Madden Garisonn $110.00 Steve Madden - Boro Steve Madden Boro $130.00 NEW!
Calvin Klein - Ulysses Calvin Klein Ulysses $140.00 Rockport - Parker Hill Desert Boot Rockport Parker Hill Desert Boot $170.00 NEW! Nunn Bush - Dodge Nunn Bush Dodge $85.00 Mark Nason SKECHERS - Morley Mark Nason SKECHERS Morley $110.00 Rated: 5 stars!
Cole Haan - Copley Chukka Boot Cole Haan Copley Chukka Boot $168.00 NEW! Frye - Walter Chukka Frye Walter Chukka $348.00 Rated: 5 stars! Calvin Klein - Ulysses Calvin Klein Ulysses $140.00 Type Z - Eliott Type Z Eliott $129.00 Rated: 3 stars!
Steve Madden - Boro Steve Madden Boro $130.00 NEW! Rockport - Parker Hill Desert Boot Rockport Parker Hill Desert Boot $170.00 NEW! Danner - Mountain Trail Danner Mountain Trail $320.00 Rated: 5 stars! Cole Haan - Cambridge Woven Chukka Cole Haan Cambridge Woven Chukka $368.00 NEW!
Polo Ralph Lauren - Torrington Chukka NT Polo Ralph Lauren Torrington Chukka NT $139.00 Nunn Bush - Dodge Nunn Bush Dodge $85.00 Wolverine - 1883 Orville Wolverine 1883 Orville $135.00 Rated: 4 stars! ECCO - Edinburgh GTX Boot ECCO Edinburgh GTX Boot $180.00 NEW!
Frye - Jack Lace Up Frye Jack Lace Up $328.00 Steve Madden - Garisonn Steve Madden Garisonn $110.00 John Varvatos - NYC Vintage Chukka John Varvatos NYC Vintage Chukka $298.00 Frye - Oliver Chukka Frye Oliver Chukka $258.00 Rated: 4 stars!
Salvatore Ferragamo - Pioneer Ankle Boot Salvatore Ferragamo Pioneer Ankle Boot $595.00 Calvin Klein - Ulysses Calvin Klein Ulysses $140.00 Polo Ralph Lauren - Torrington Chukka NT Polo Ralph Lauren Torrington Chukka NT $139.00 John Varvatos - NYC Vintage Chukka John Varvatos NYC Vintage Chukka $298.00
Vasque - Summit GTX Vasque Summit GTX $219.95 Rated: 4 stars! La Sportiva - Karakorum La Sportiva Karakorum $305.00 Rated: 5 stars! Frye - Oliver Chukka Frye Oliver Chukka $258.00 Rated: 4 stars! Lloyd - Lake Lloyd Lake $329.00
Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $155.00 NEW! Wolverine - Francisco Chukka Wolverine Francisco Chukka $175.00 NEW! Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $155.00 NEW! Florsheim - Rockit Chukka Florsheim Rockit Chukka $130.00 NEW!
Nunn Bush - Dodge Nunn Bush Dodge $85.00 Frye - Walter Chukka Frye Walter Chukka $348.00 Rated: 5 stars! Frye - Walter Chukka Frye Walter Chukka $348.00 Rated: 5 stars! Calvin Klein Jeans - Orrick Calvin Klein Jeans Orrick $130.00
SKECHERS - Bruiser SKECHERS Bruiser $69.00 NEW! 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! John Varvatos - Hipster Laceless Chukka John Varvatos Hipster Laceless Chukka $198.00 Rated: 4 stars!
John Varvatos - Hipster Chukka John Varvatos Hipster Chukka $198.00 Rated: 4 stars! Harley-Davidson - Beau Harley-Davidson Beau $170.00 Harley-Davidson - Beau Harley-Davidson Beau $170.00 Wolverine - Francisco Chukka Wolverine Francisco Chukka $175.00 NEW!
Frye - Jack Lace Up Frye Jack Lace Up $328.00 Steve Madden - Handler Steve Madden Handler $90.00 NEW! Polo Ralph Lauren - Torrington Chukka NT Polo Ralph Lauren Torrington Chukka NT $139.00 Original Penguin - Birdie Original Penguin Birdie $180.00 NEW!
Frye - Dakota Mid Lace Frye Dakota Mid Lace $248.00 Rated: 5 stars! Wolverine - 1883 Orville Wolverine 1883 Orville $135.00 Rated: 4 stars! Wolverine - 1883 Orville Wolverine 1883 Orville $135.00 Rated: 4 stars! Frye - James Lug Chukka Frye James Lug Chukka $268.00 Rated: 5 stars!
Frye - Phillip Wingtip Chukka Frye Phillip Wingtip Chukka $278.00 Frye - Walter Chukka Frye Walter Chukka $348.00 Rated: 5 stars! Roper - Performance 2-Eyelet Ankle Boot Roper Performance 2-Eyelet Ankle Boot $120.00 Rated: 4 stars! Frye - Carter Chukka Frye Carter Chukka $248.00
Frye - Carter Chukka Frye Carter Chukka $248.00 Lloyd - Lake Lloyd Lake $329.00 Salvatore Ferragamo - Pioneer Ankle Boot Salvatore Ferragamo Pioneer Ankle Boot $595.00 Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $155.00 NEW!
Frye - Jack Lace Up Frye Jack Lace Up $328.00 UGG - Brompton Tweed UGG Brompton Tweed $195.00 NEW! Cole Haan - Copley Chukka Boot Cole Haan Copley Chukka Boot $168.00 NEW! Cole Haan - Copley Chukka Boot Cole Haan Copley Chukka Boot $168.00 NEW!
Steve Madden - Handler Steve Madden Handler $90.00 NEW! Steve Madden - Handler Steve Madden Handler $90.00 NEW! Polo Ralph Lauren - Torrington Chukka NT Polo Ralph Lauren Torrington Chukka NT $139.00 Kenneth Cole Reaction - Had 2 B U Kenneth Cole Reaction Had 2 B U $138.00 NEW!
La Sportiva - Trango S EVO GTX La Sportiva Trango S EVO GTX $320.00 Rated: 5 stars! La Sportiva - Trango Extreme EVO Light GTX® La Sportiva Trango Extreme EVO Light GTX® $420.00 Rated: 5 stars! Frye - Dakota Mid Lace Frye Dakota Mid Lace $248.00 Rated: 5 stars! Frye - Dakota Mid Lace Frye Dakota Mid Lace $248.00 Rated: 5 stars!
Roper - Performance 2-Eyelet Ankle Boot Roper Performance 2-Eyelet Ankle Boot $125.00 Rated: 4 stars! Lloyd - Gibson Lloyd Gibson $249.00 Frye - Carter Chukka Frye Carter Chukka $248.00 John Varvatos - Hipster Laceless Chukka John Varvatos Hipster Laceless Chukka $198.00 Rated: 4 stars!
Trask - Brady Trask Brady $265.00 Trask - Brady Trask Brady $265.00 Dr. Scholl's - Da Capo - Original Collection Dr. Scholl's Da Capo - Original Collection $100.00 UGG - Brompton UGG Brompton $195.00 NEW!
Zappos Family Core Value:

10. Be Humble