“chukka and Boots” we found 229 items!

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Frye - William Monk Chukka Frye William Monk Chukka $358.00 Frye - William Monk Chukka Frye William Monk Chukka $358.00 Woolrich - Yankee Woolrich Yankee $325.00 Rated: 4 stars! Red Wing Heritage - Blacksmith 6 Red Wing Heritage Blacksmith 6" Round Toe $300.00 Rated: 5 stars!
Trask - Irving Trask Irving $295.00 Trask - Irving Trask Irving $295.00 Red Wing Heritage - Foreman Chukka Red Wing Heritage Foreman Chukka $290.00 Rated: 5 stars! Red Wing Heritage - Foreman Chukka Red Wing Heritage Foreman Chukka $290.00 Rated: 5 stars!
Trask - Arlington Trask Arlington $275.00 Rated: 5 stars! Trask - Arlington Trask Arlington $275.00 Rated: 5 stars! Red Wing Heritage - Work Chukka Red Wing Heritage Work Chukka $260.00 Rated: 4 stars! Red Wing Heritage - Work Chukka Red Wing Heritage Work Chukka $260.00 Rated: 4 stars!
Trask - Brady Trask Brady $245.00 Rated: 5 stars! ECCO - Turn GTX Boot ECCO Turn GTX Boot $230.00 Rated: 5 stars! ECCO - Turn GTX Boot ECCO Turn GTX Boot $230.00 Rated: 5 stars! Frye - Mason Chukka Frye Mason Chukka $228.00 Rated: 4 stars!
Frye - Mason Chukka Frye Mason Chukka $228.00 Rated: 4 stars! Sperry Top-Sider - Gold Chukka Boot Sperry Top-Sider Gold Chukka Boot $225.00 Sperry Top-Sider - Gold Chukka Boot Sperry Top-Sider Gold Chukka Boot $225.00 Sperry Top-Sider - Gold Annapolis Boot Sperry Top-Sider Gold Annapolis Boot $225.00
Ted Baker - Torsdi 2 Ted Baker Torsdi 2 $220.00 Rated: 4 stars! Ted Baker - Torsdi 3 Ted Baker Torsdi 3 $220.00 Rated: 3 stars! Ted Baker - Torsdi 4 Ted Baker Torsdi 4 $220.00 Ted Baker - Torsdi 4 Ted Baker Torsdi 4 $220.00
Thorogood - Lace To Toe Roofer Thorogood Lace To Toe Roofer $212.00 Rated: 5 stars! Donald J Pliner - Ermes Donald J Pliner Ermes $235.00 $210.99 Chippewa - Chukka Chippewa Chukka $207.00 Rated: 5 stars! Naot Footwear - Pilot Naot Footwear Pilot $200.00 Rated: 5 stars!
Naot Footwear - Pilot Naot Footwear Pilot $200.00 Rated: 5 stars! Naot Footwear - Pilot Naot Footwear Pilot $199.95 Rated: 5 stars! Chippewa - Handswen Casual Chukka Chippewa Handswen Casual Chukka $265.95 $199.46 John Varvatos - Hipster Chukka John Varvatos Hipster Chukka $198.00 Rated: 4 stars!
Ted Baker - Torsdi 4 Ted Baker Torsdi 4 $220.00 $197.99 Wolverine - Hensel Wolverine Hensel $195.00 Pikolinos - Kimberley W3C-7602 Pikolinos Kimberley W3C-7602 $190.00 Rated: 5 stars! Pikolinos - Kimberley W3C-7602 Pikolinos Kimberley W3C-7602 $190.00 Rated: 5 stars!
Josef Seibel - Oscar 23 Josef Seibel Oscar 23 $190.00 Blondo - Gustave Waterproof Blondo Gustave Waterproof $190.00 Timberland - Britton Hill Waterproof Chukka Timberland Britton Hill Waterproof Chukka $180.00 Rated: 5 stars! Timberland - Britton Hill Waterproof Chukka Timberland Britton Hill Waterproof Chukka $180.00 Rated: 5 stars!
Stacy Adams - Madison II - 65 Stacy Adams Madison II - 65 $180.00 Rated: 4 stars! Pikolinos - Kimberley W3C-8509 Pikolinos Kimberley W3C-8509 $180.00 Rated: 5 stars! Wolverine - Hensel Wolverine Hensel $195.00 $175.99 Ted Baker - Torsdi 4 Ted Baker Torsdi 4 $220.00 $175.99
Harley-Davidson - Beau Harley-Davidson Beau $174.00 Blundstone - BL268 Blundstone BL268 $169.95 Rated: 4 stars! Irish Setter - Borderland Chukka Irish Setter Borderland Chukka $190.00 $169.95 Rated: 4 stars! Blundstone - BL278 Blundstone BL278 $169.95
Ted Baker - Torsdi 4 Ted Baker Torsdi 4 $220.00 $165.00 Donald J Pliner - Ermes Donald J Pliner Ermes $235.00 $164.99 Pikolinos - Chile 01G-5056NG Pikolinos Chile 01G-5056NG $180.00 $162.99 Pikolinos - Chile 01G-5056NG Pikolinos Chile 01G-5056NG $180.00 $162.99
Geox - MRUBBIANOBABX5 Geox MRUBBIANOBABX5 $230.00 $161.00 Eastland 1955 Edition - Oneida 1955 Eastland 1955 Edition Oneida 1955 $160.00 Rated: 4 stars! Eastland 1955 Edition - Oneida 1955 Eastland 1955 Edition Oneida 1955 $160.00 Rated: 4 stars! Josef Seibel - Sienna 03 Josef Seibel Sienna 03 $160.00 Rated: 5 stars!
Josef Seibel - Sienna 03 Josef Seibel Sienna 03 $160.00 Rated: 5 stars! Josef Seibel - Sienna 03 Josef Seibel Sienna 03 $160.00 Rated: 5 stars! Pikolinos - Mackenzie M0C-8028NG Pikolinos Mackenzie M0C-8028NG $200.00 $159.99 Wolverine - Hensel Wolverine Hensel $195.00 $155.95
Dunham - REVseek Dunham REVseek $155.00 Rated: 3 stars! Bed Stu - Curtis Bed Stu Curtis $155.00 Rated: 5 stars! Johnston & Murphy - Copeland Chukka Johnston & Murphy Copeland Chukka $154.95 Rated: 4 stars! Johnston & Murphy - Copeland Chukka Johnston & Murphy Copeland Chukka $154.95 Rated: 4 stars!
Johnston & Murphy - Copeland Chukka Johnston & Murphy Copeland Chukka $154.95 Rated: 4 stars! Massimo Matteo - Suede Chukka Massimo Matteo Suede Chukka $169.00 $152.99 Rated: 5 stars! Dunham - REVdash Dunham REVdash $150.00 Rated: 4 stars! Dunham - REVdash Dunham REVdash $150.00 Rated: 4 stars!
Dunham - REVdash Dunham REVdash $150.00 Rated: 4 stars! Dunham - Addison Dunham Addison $150.00 Rated: 4 stars! Clarks - Un Astin Clarks Un Astin $150.00 Clarks - Un Astin Clarks Un Astin $150.00
Harley-Davidson - Candler Harley-Davidson Candler $150.00 Harley-Davidson - Candler Harley-Davidson Candler $150.00 Vivobarefoot - Gobi II M Leather Vivobarefoot Gobi II M Leather $150.00 Rated: 4 stars! Rieker - F1310 Rieker F1310 $150.00
Bed Stu - Keith Bed Stu Keith $165.00 $149.99 Rated: 5 stars! Timberland - Authentics Chukka Timberland Authentics Chukka $160.00 $144.99 Clarks - Desert Trek Clarks Desert Trek $140.00 Rated: 4 stars! Clarks - Desert Trek Clarks Desert Trek $140.00 Rated: 4 stars!
Dr. Martens - 1919 Dr. Martens 1919 $140.00 Rated: 5 stars! Dr. Martens - 1914 Dr. Martens 1914 $140.00 Rated: 4 stars! Clarks - Wallabee Boot Clarks Wallabee Boot $140.00 Rated: 5 stars! Oliberte - Mogado Hi Oliberte Mogado Hi $140.00
Sperry Top-Sider - A/O Lug Boat Chukka Waterproof Boot Sperry Top-Sider A/O Lug Boat Chukka Waterproof Boot $140.00 Sperry Top-Sider - A/O Lug Boat Chukka Waterproof Boot Sperry Top-Sider A/O Lug Boat Chukka Waterproof Boot $140.00 Massimo Matteo - 3-Eye Chukka Massimo Matteo 3-Eye Chukka $169.00 $135.99 Rated: 5 stars! Dr. Martens - 1460 W Dr. Martens 1460 W $135.00 Rated: 5 stars!
Dr. Martens - Diego 7 Tie Lace To Toe Boot Dr. Martens Diego 7 Tie Lace To Toe Boot $135.00 Rated: 5 stars! Clarks - Stratton Limit Clarks Stratton Limit $135.00 Rated: 5 stars! Clarks - Stratton Limit Clarks Stratton Limit $135.00 Rated: 5 stars! Clarks - Newkirk Top Clarks Newkirk Top $135.00 Rated: 5 stars!
Clarks - Newkirk Top Clarks Newkirk Top $135.00 Rated: 5 stars! Rieker - F1301 Rieker F1301 $135.00 Wolverine - Ranger 6 Wolverine Ranger 6" Moc Toe $135.00 Florsheim - Frisco Chukka Boot Florsheim Frisco Chukka Boot $135.00 Rated: 5 stars!
Pikolinos - Chile 01G-5056 Pikolinos Chile 01G-5056 $165.00 $132.99 Merrell - Ashland Chukka Merrell Ashland Chukka $129.95 Rated: 5 stars! Timberland - Authentics Chukka Timberland Authentics Chukka $160.00 $127.99 Clarks - Varick Hill Clarks Varick Hill $140.00 $125.99 Rated: 4 stars!