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 312 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.

Ariat - Ariat Rambler Ariat Ariat Rambler $149.95 Rated: 5 stars! Bed Stu - Draco Bed Stu Draco $135.00 Rated: 5 stars! Chippewa - American Handcrafted GQ Apache Lacer Boot Chippewa American Handcrafted GQ Apache Lacer Boot $179.00 Rated: 5 stars! Timberland PRO - Magnus 6 Timberland PRO Magnus 6" Steel Toe $113.00 Rated: 5 stars!
Danner - Bull Run Christy ST Danner Bull Run Christy ST $189.00 John Varvatos - Hipster Work Boot John Varvatos Hipster Work Boot $107.99 $198.00 Rated: 4 stars! SALE! Chippewa - Apache Lace Up Chippewa Apache Lace Up $185.00 Rated: 5 stars! Bed Stu - Revolution Bed Stu Revolution $82.99 $135.00 Rated: 5 stars! SALE!
Ted Baker - Torsdi 2 Ted Baker Torsdi 2 $147.99 $210.00 SALE! Bed Stu - Innovator Bed Stu Innovator $109.99 $135.00 Rated: 4 stars! SALE! Type Z - Timmy Type Z Timmy $90.99 $129.00 Rated: 4 stars! SALE! Bed Stu - Patriot Bed Stu Patriot $150.00 Rated: 4 stars!
Frye - James Chukka Frye James Chukka $258.00 Rated: 4 stars! Blundstone - BL1306 Blundstone BL1306 $155.00 Rated: 4 stars! Ariat - Ariat Rambler Ariat Ariat Rambler $159.95 Rated: 5 stars! Ariat - Ariat Rambler Ariat Ariat Rambler $159.95 Rated: 5 stars!
Dan Post - Tyree Dan Post Tyree $165.99 $237.00 Rated: 5 stars! SALE! Type Z - Taylor Type Z Taylor $90.99 $129.00 Rated: 4 stars! SALE! Type Z - Lee Type Z Lee $90.99 $129.00 Rated: 4 stars! SALE! Caterpillar - Runyan Mid Caterpillar Runyan Mid $90.00 Rated: 5 stars!
SKECHERS - Bruiser SKECHERS Bruiser $55.99 $69.00 SALE! Durango - SW542 Durango SW542 $144.99 Rated: 5 stars! Blundstone - BL1314 Blundstone BL1314 $150.00 Rated: 5 stars! Laredo - Macon Laredo Macon $139.00 Rated: 5 stars!
Dingo - DI5110 Dingo DI5110 $154.00 Rated: 5 stars! Frye - Tyler Lace Up Frye Tyler Lace Up $298.00 Rated: 4 stars! Ariat - Rambler Flint Ariat Rambler Flint $112.99 $159.95 SALE! Polo Ralph Lauren - Tedd Polo Ralph Lauren Tedd $69.99 $98.00 Rated: 4 stars! SALE!
Carhartt - 6-Inch Work-Flex™ Composite Toe Work Boot Carhartt 6-Inch Work-Flex™ Composite Toe Work Boot $134.99 Rated: 5 stars! Justin - BR734 Justin BR734 $132.99 $190.00 Rated: 5 stars! SALE! Caterpillar - Runyan Mid Caterpillar Runyan Mid $90.00 Rated: 5 stars! Ariat - Rambler Work Pull-On SD Comp Toe Ariat Rambler Work Pull-On SD Comp Toe $189.95
Ariat - Holbrook Ariat Holbrook $109.95 Rated: 5 stars! Type Z - Renton Type Z Renton $115.99 $129.00 SALE! Frye - Fulton Chelsea Frye Fulton Chelsea $214.99 $268.00 Rated: 4 stars! SALE! Blundstone - BL584 Blundstone BL584 $200.00 Rated: 5 stars!
Bed Stu - Stand Up to Cancer Burst Bed Stu Stand Up to Cancer Burst $140.00 Rated: 4 stars! Frye - Smith Harness Frye Smith Harness $298.00 Rated: 5 stars! Blundstone - BL1320 Blundstone BL1320 $165.00 Rated: 5 stars! Ariat - Sport Brumby Ariat Sport Brumby $104.99 $149.95 Rated: 5 stars! SALE!
SKECHERS Work - On Site - Verto SKECHERS Work On Site - Verto $105.00 Dr. Martens Work - 2296 Wellington NS Dr. Martens Work 2296 Wellington NS $130.00 Rated: 4 stars! Ariat - Rambler Work Pull-On Ariat Rambler Work Pull-On $169.95 Rated: 5 stars! Frye - Phillip Harness Frye Phillip Harness $288.00 Rated: 5 stars!
Frye - Smith Harness Frye Smith Harness $298.00 Rated: 5 stars! Calvin Klein Jeans - Palmer Calvin Klein Jeans Palmer $97.99 $140.00 SALE! Blundstone - BL1301 Blundstone BL1301 $155.00 Rated: 5 stars! Ariat - Rambler R Toe Ariat Rambler R Toe $169.96 Rated: 5 stars!
Irish Setter - Borderland Chukka Irish Setter Borderland Chukka $179.99 Rated: 4 stars! Type Z - Lee Type Z Lee $90.99 $129.00 Rated: 4 stars! SALE! Justin - WK4986 - Waterproof Justin WK4986 - Waterproof $125.00 Rated: 5 stars! Lucchese - M2600.74 Lucchese M2600.74 $359.00 Rated: 5 stars!
Ariat - Quantum Pro Ariat Quantum Pro $189.99 $269.95 SALE! Ariat - Crossbred Ariat Crossbred $147.99 $209.95 SALE! Chippewa - American Handcrafted GQ Tan Rodeo Boot Chippewa American Handcrafted GQ Tan Rodeo Boot $179.00 Rated: 5 stars! Harley-Davidson - Scout Harley-Davidson Scout $150.00 Rated: 4 stars!
Harley-Davidson - Constrictor Harley-Davidson Constrictor $117.99 $168.00 Rated: 5 stars! SALE! Justin - 444 Justin 444 $191.00 Rated: 5 stars! Ariat - Heritage Reinsman Ariat Heritage Reinsman $125.99 $179.95 Rated: 5 stars! SALE! Bed Stu - Post Bed Stu Post $164.99 $235.00 Rated: 4 stars! SALE!
Frye - Smith Harness Frye Smith Harness $298.00 Rated: 5 stars! John Varvatos - Barrett Side Zip Boot John Varvatos Barrett Side Zip Boot $209.99 $298.00 Rated: 4 stars! SALE! Ariat - Holbrook Ariat Holbrook $79.99 $109.95 Rated: 5 stars! SALE! Lumiani International Collection - Sabia Lumiani International Collection Sabia $69.99 $99.00 Rated: 3 stars! SALE!
Red Wing Heritage - 6 Red Wing Heritage 6" Round Toe Lug $270.00 Rated: 5 stars! Type Z - Kent Type Z Kent $115.99 $129.00 SALE! Frye - James Inside Zip Frye James Inside Zip $278.00 Rated: 4 stars! Frye - Fulton Lace Up Frye Fulton Lace Up $139.99 $278.00 Rated: 4 stars! SALE!
Frye - Phillip Inside Zip Frye Phillip Inside Zip $298.00 Rated: 5 stars! Bed Stu - Innovator Bed Stu Innovator $135.00 Rated: 4 stars! Harley-Davidson - Scout Harley-Davidson Scout $150.00 Rated: 4 stars! Harley-Davidson - Ranger Harley-Davidson Ranger $87.99 $160.00 Rated: 2 stars! SALE!
Frye - James Chukka Frye James Chukka $258.00 Rated: 4 stars! Frye - Phillip Harness Frye Phillip Harness $298.00 Rated: 5 stars! Bed Stu - Bolter Bed Stu Bolter $140.99 $235.00 Rated: 5 stars! SALE! Frye - Smith Engineer Frye Smith Engineer $298.00 Rated: 4 stars!
Frye - Chambers High Frye Chambers High $148.00 Rated: 4 stars! Blundstone - BL1322 Blundstone BL1322 $140.00 Frye - Oliver Chukka Frye Oliver Chukka $258.00 Rated: 4 stars! Laredo - Thomson Laredo Thomson $148.50 $165.00 SALE!
Justin - 4472 Justin 4472 $136.00 Rated: 5 stars! Tony Lama - RR3307 Tony Lama RR3307 $119.99 $171.00 SALE! Robert Wayne - Roma Robert Wayne Roma $89.95 Rated: 4 stars! Lucchese - M2611.54 Lucchese M2611.54 $244.99 $349.00 Rated: 5 stars! SALE!
Ariat - Sierra Wide Square Toe Puncture Resistant Steel Toe Ariat Sierra Wide Square Toe Puncture Resistant Steel Toe $125.99 $179.95 SALE! John Varvatos - Dress Artisan Chukka John Varvatos Dress Artisan Chukka $449.99 $750.00 SALE! Justin - 1830 Justin 1830 $139.99 $199.00 Rated: 5 stars! SALE! Type Z - Renton Type Z Renton $115.99 $129.00 SALE!
J. Shoes - Fellow J. Shoes Fellow $160.00 $230.00 SALE! Lobo Solo - Albert Lobo Solo Albert $110.00 Frye - James Inside Zip Frye James Inside Zip $278.00 Rated: 4 stars! Dingo - Rev Up Dingo Rev Up $134.00 Rated: 4 stars!
Frye - Harvey Outside Zip Frye Harvey Outside Zip $298.00 Rated: 5 stars! Harley-Davidson - Ranger Harley-Davidson Ranger $104.99 $160.00 Rated: 2 stars! SALE! Stetson - Snip Toe Harness W/ Bleach Boot Stetson Snip Toe Harness W/ Bleach Boot $285.00 Rated: 5 stars! Justin - 4444 Justin 4444 $169.99 $199.00 Rated: 5 stars! SALE!
Frye - Dakota Crepe Plain Toe Frye Dakota Crepe Plain Toe $212.99 $328.00 Rated: 5 stars! SALE! Frye - Dean Harness Frye Dean Harness $190.99 $348.00 Rated: 2 stars! SALE! Frye - Jake Engineer Frye Jake Engineer $239.99 $298.00 Rated: 5 stars! SALE! Frye - James Lug Wingtip Boot Frye James Lug Wingtip Boot $279.99 $328.00 Rated: 5 stars! SALE!
Zappos Family Core Value:

10. Be Humble