free-shipping

“chukka and Men Boots” we found 538 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.

Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! Rockport - Essential Details Waterproof Dress Chukka Rockport Essential Details Waterproof Dress Chukka $110.00 Rated: 4 stars! Timberland - Earthkeepers® Brook Park Chukka Timberland Earthkeepers® Brook Park Chukka $130.00 Rated: 5 stars! Born - Harrison Born Harrison $99.00 Rated: 4 stars!
Clarks - Senner Ave Clarks Senner Ave $90.00 Rated: 4 stars! Timberland - Earthkeepers® City Lite Waterproof Chukka Timberland Earthkeepers® City Lite Waterproof Chukka $120.00 Rated: 4 stars! Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! Clarks - Stratton Limit Clarks Stratton Limit $135.00 Rated: 5 stars!
Vivobarefoot - Gobi II M Leather Vivobarefoot Gobi II M Leather $150.00 Rated: 4 stars! Florsheim - Rockit Chukka Boot Florsheim Rockit Chukka Boot $135.00 Rated: 4 stars! Rockport - RocSports Lite ZoneCush Plain Toe Boot Rockport RocSports Lite ZoneCush Plain Toe Boot $120.00 Rated: 5 stars! Timberland - Earthkeepers® Brook Park Chukka Timberland Earthkeepers® Brook Park Chukka $130.00 Rated: 5 stars!
Merrell - Realm Chukka Merrell Realm Chukka $150.00 Rated: 4 stars! Nunn Bush - Woodbury Plain Toe Casual Chukka Boot Nunn Bush Woodbury Plain Toe Casual Chukka Boot $60.00 Rated: 5 stars! Robert Wayne - Brent Robert Wayne Brent $49.99 Rated: 3 stars! ECCO - Turn GTX Boot ECCO Turn GTX Boot $225.00 Rated: 5 stars!
Timberland - Earthkeepers® City Lite Chukka Timberland Earthkeepers® City Lite Chukka $100.00 Rated: 4 stars! Rockport - Ledge Hill 2 Chukka Boot Rockport Ledge Hill 2 Chukka Boot $150.00 Rated: 4 stars! ECCO - Turn GTX Boot ECCO Turn GTX Boot $225.00 Rated: 5 stars! Timberland - Earthkeepers® City Lite Waterproof Chukka Timberland Earthkeepers® City Lite Waterproof Chukka $120.00 Rated: 4 stars!
Deer Stags - Seattle Deer Stags Seattle $80.00 Rated: 5 stars! Florsheim - Jet Chukka Boot Florsheim Jet Chukka Boot $135.00 Rated: 5 stars! Rockport - Ledge Hill 2 Chukka Boot Rockport Ledge Hill 2 Chukka Boot $150.00 Rated: 4 stars! Rockport - RocSports Lite ZoneCush Plain Toe Boot Rockport RocSports Lite ZoneCush Plain Toe Boot $120.00 Rated: 5 stars!
UGG - Kaldwell UGG Kaldwell $139.95 Rated: 5 stars! Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! Keen - Tyretread Boot Keen Tyretread Boot $140.00 Rated: 5 stars! Rockport - RocSports Lite 2 Chukka Rockport RocSports Lite 2 Chukka $120.00 Rated: 4 stars!
Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! Rockport - Essential Details Waterproof Dress Chukka Rockport Essential Details Waterproof Dress Chukka $110.00 Rated: 4 stars! Dunham - Addison Dunham Addison $140.00 Rated: 4 stars! Clarks - Senner Ave Clarks Senner Ave $90.00 Rated: 4 stars!
Nunn Bush - Woodbury Plain Toe Casual Chukka Boot Nunn Bush Woodbury Plain Toe Casual Chukka Boot $60.00 Rated: 5 stars! Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! Florsheim - Doon Chukka Boot Florsheim Doon Chukka Boot $120.00 Rated: 4 stars! Rockport - RocSports Lite 2 Chukka Rockport RocSports Lite 2 Chukka $120.00 Rated: 4 stars!
Timberland - Earthkeepers® City Lite Chukka Timberland Earthkeepers® City Lite Chukka $100.00 Rated: 4 stars! John Varvatos - Hipster Chukka John Varvatos Hipster Chukka $198.00 Rated: 4 stars! Born - Twain Born Twain $119.00 Rated: 4 stars! Clarks - Jink Desert Clarks Jink Desert $115.00 Rated: 5 stars!
Clarks - Desert Trek Clarks Desert Trek $120.00 Rated: 5 stars! Clarks - Wallabee Boot Clarks Wallabee Boot $140.00 Rated: 5 stars! SKECHERS - Mariner SKECHERS Mariner $69.00 Rated: 4 stars! Dunham - Addison Dunham Addison $140.00 Rated: 4 stars!
UGG - Deklan UGG Deklan $129.95 UGG - Leighton UGG Leighton $159.95 Rated: 4 stars! Florsheim - Rockit Chukka Boot Florsheim Rockit Chukka Boot $135.00 Rated: 4 stars! Nunn Bush - Dodge Nunn Bush Dodge $68.00 Rated: 4 stars!
Steve Madden - Harsen Steve Madden Harsen $80.00 Rated: 4 stars! Timberland - Earthkeepers® Brook Park Chukka Timberland Earthkeepers® Brook Park Chukka $130.00 Rated: 5 stars! Dunham - REVdash Dunham REVdash $150.00 Rated: 4 stars! Red Wing Heritage - Blacksmith 6 Red Wing Heritage Blacksmith 6" Round Toe $300.00 Rated: 5 stars!
Red Wing Heritage - Work Chukka Red Wing Heritage Work Chukka $260.00 Rated: 5 stars! Clarks - Wallabee Boot Clarks Wallabee Boot $140.00 Rated: 5 stars! Clarks - Exton Up Clarks Exton Up $140.00 Dr. Martens - 1919 Dr. Martens 1919 $140.00 Rated: 5 stars!
Dr. Martens Work - Ironbridge ST Dr. Martens Work Ironbridge ST $140.00 Rated: 4 stars! Florsheim - Jet Chukka Boot Florsheim Jet Chukka Boot $135.00 Rated: 5 stars! Bed Stu - Draco Bed Stu Draco $135.00 Rated: 4 stars! Timberland - Earthkeepers® Britton Hill Chukka Timberland Earthkeepers® Britton Hill Chukka $170.00 Rated: 5 stars!
Dr. Martens - Mayport 2-Eye Desert Boot Dr. Martens Mayport 2-Eye Desert Boot $70.00 Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! UGG - Kaldwell UGG Kaldwell $139.95 Rated: 5 stars! Johnston & Murphy - Copeland Chukka Johnston & Murphy Copeland Chukka $149.95 Rated: 5 stars!
UGG - Freamon UGG Freamon $99.95 NEW! Dr. Martens - Barnie Chukka Boot Dr. Martens Barnie Chukka Boot $120.00 Rated: 4 stars! SeaVees - 12/67 3 Eye Chukka SeaVees 12/67 3 Eye Chukka $178.00 Rated: 5 stars! Steve Madden - Hestonn Steve Madden Hestonn $85.00 Rated: 4 stars!
Wolverine - Orville Desert Boot Wolverine Orville Desert Boot $155.00 Rated: 4 stars! Born - Asten Born Asten $105.00 Rated: 4 stars! UGG - Freamon UGG Freamon $99.95 NEW! UGG - Freamon UGG Freamon $99.95 NEW!
Merrell - Realm Chukka Merrell Realm Chukka $150.00 Rated: 4 stars! The North Face - Ballard II Chukka The North Face Ballard II Chukka $130.00 Rated: 5 stars! UGG - Leighton UGG Leighton $159.95 Rated: 4 stars! Robert Wayne - Brent Robert Wayne Brent $49.99 Rated: 3 stars!
UGG - Freamon UGG Freamon $109.95 NEW! Rockport - RocSports Lite 2 Chukka Rockport RocSports Lite 2 Chukka $120.00 Rated: 4 stars! Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! Timberland - Earthkeepers® Rugged LT Chukka Timberland Earthkeepers® Rugged LT Chukka $140.00 NEW!
Clarks - Desert Boot Clarks Desert Boot $130.00 Rated: 5 stars! NEW! Born - Axe II Born Axe II $115.00 Rated: 4 stars! Blundstone - BL268 Blundstone BL268 $159.00 Rated: 4 stars! Steve Madden - Hestonn Steve Madden Hestonn $85.00 Rated: 4 stars!
ECCO - Edinburgh GTX Boot ECCO Edinburgh GTX Boot $180.00 Rated: 5 stars! Clarks - Stratton Limit Clarks Stratton Limit $135.00 Rated: 5 stars! Rockport - Rocsports Lite - Es Waterproof Mocc Toe Mudguard Boot Rockport Rocsports Lite - Es Waterproof Mocc Toe Mudguard Boot $150.00 Rated: 4 stars! UGG - Leighton UGG Leighton $159.95 Rated: 4 stars!
Dr. Martens - Barnie Chukka Boot Dr. Martens Barnie Chukka Boot $120.00 Rated: 4 stars! Polo Ralph Lauren - Tedd Polo Ralph Lauren Tedd $98.00 Rated: 4 stars! Danner - Mountain Light™ II Danner Mountain Light™ II $309.00 Rated: 4 stars! Timberland - Earthkeepers® Britton Hill Chukka Timberland Earthkeepers® Britton Hill Chukka $170.00 Rated: 5 stars!
Clarks - Wallabee Boot Clarks Wallabee Boot $140.00 Rated: 5 stars! Ariat - Lookout Ariat Lookout $129.95 Clarks - Jink Desert Clarks Jink Desert $115.00 Rated: 5 stars! Nunn Bush - Dodge Nunn Bush Dodge $68.00 Rated: 4 stars!
Lacoste - Sherbrooke-Hi 13 Lacoste Sherbrooke-Hi 13 $159.95 John Varvatos - Hipster Chukka John Varvatos Hipster Chukka $198.00 Rated: 4 stars! Steve Madden - Hestonn Steve Madden Hestonn $85.00 Rated: 4 stars! Bed Stu - Randall Bed Stu Randall $210.00 Rated: 4 stars!
Zappos Family Core Value:

10. Be Humble