Free Delivery by Christmas
Cole Haan Roundhill Grand Waterproof Chukka Boot (Men)
Current Price $260
Men's Brown Chukka Boots
Free Delivery by Christmas
Allen Edmonds Chandler Chukka Boot (Men)
Current Price $525
Free Delivery by Christmas
Frye Paul Suede Chukka Boot (Men)
Current Price $188 to $198
Free Delivery by Christmas
TO BOOT NEW YORK Richard Chukka Boot (Men)
Current Price $450
Free Delivery by Christmas
Johnston & Murphy Upton Chukka (Men)
Current Price $119.99
Previous Price $179
Free Delivery by Christmas
Vince Jerome Chukka Boot (Men)
Current Price $298
Free Delivery by Christmas
Vince Camuto Presely Chukka Boot (Men)
Current Price $169
Free Delivery by Christmas
Aquatalia Golliard Water Resistant Chukka Boot (Men)
Current Price $495
Free Delivery by Christmas
Frye Paul Chukka (Men)
Current Price $188 to $198
Free Delivery by Christmas
Johnston & Murphy Calder Chukka Boot (Men)
Current Price $179
Free Delivery by Christmas
Gordon Rush Austin Chukka Boot (Men)
Current Price $290
Free Delivery by Christmas
Vince Jerome Suede Lugged Chukka Boot (Men) (Nordstrom Exclusive)
Current Price $298
Free Delivery by Christmas
Barbour Meays Chukka Boot (Men)
Current Price $230
Free Delivery by Christmas
UGG® Neumel Chukka Boot (Men)
Current Price $149.95
Free Delivery by Christmas
TO BOOT NEW YORK Monaco Plain Toe Chukka Boot (Men)
Current Price $425
Free Delivery by Christmas
SOREL Madson II Waterproof Chukka Boot (Men)
Current Price $190
Free Delivery by Christmas
Alden Burnished Chukka Boot (Men)
Current Price $682
Free Delivery by Christmas
TOMS Navi Water Resistant Chukka Boot (Men)
Current Price $140
Free Delivery by Christmas
ECCO Metropole London Waterproof Suede Chukka Boot (Men)
Current Price $229.95
Free Delivery by Christmas
Johnston & Murphy Upton Chukka (Men)
Current Price $179
Free Delivery by Christmas
Johnston & Murphy Braxton Chukka Boot (Men)
Current Price $159
Free Delivery by Christmas
Bruno Magli Cat Walk Chukka Boot (Men)
Current Price $350
Free Delivery by Christmas
Mephisto Berto Chukka Boot (Men)
Current Price $439
Free Delivery by Christmas
Robert Barakett Nicky Chukka (Men)
Current Price $298
Free Delivery by Christmas
UGG® Neumel Era Chukka Boot (Men)
Current Price $119.96
Previous Price $159.95
Free Delivery by Christmas
Clarks® Originals Clarks® Desert Chukka Boot (Men)
Current Price $150
Free Delivery by Christmas
Kenneth Cole New York Wilhem Chukka Boot (Men)
Current Price $165
Free Delivery by Christmas
Blake Mckay Dixon Chukka Boot (Men)
Current Price $119.90 to $175
Previous Price $175
Free Delivery by Christmas
Johnston & Murphy Calder 175th Chukka Boot (Men)
Current Price $175
Free Delivery by Christmas
MORJAS The Chukka Boot (Men)
Current Price $430
Free Delivery by Christmas
Johnston & Murphy Calder Oiled Suede Chukka Boot (Men)
Current Price $179
Free Delivery by Christmas
Robert Barakett Nelson Chukka (Men)
Current Price $298
Free Delivery by Christmas
John Varvatos Varick Chukka Boot (Men)
Current Price $398
Free Delivery by Christmas
Florsheim Anthem Plain Toe Chukka (Men)
Current Price $145
Free Delivery by Christmas
John Varvatos Varick Leather Chukka Boot (Men)
Current Price $398
Free Delivery by Christmas
Barbour Readhead Chukka Boot (Men)
Current Price $220
Free Delivery by Christmas
Nordstrom Italian Collection Saluzzo Chukka Boot (Men)
Current Price $229.95
Free Delivery by Christmas
Barbour Blaine Chukka Boot (Men)
Current Price $245
Free Delivery by Christmas
Barbour Hadston Chukka Boot (Men)
Current Price $240
Free Delivery by Christmas
Sperry Mini Lug Chukka Boot (Men)
Current Price $150
Free Delivery by Christmas
Florsheim Traveler Chukka Boot (Men)
Current Price $135
Free Delivery by Christmas
Alden Barrie Chukka Boot (Men)
Current Price $682
Free Delivery by Christmas
Magnanni Maurilio Chukka Boot (Men)
Current Price $550
Free Delivery by Christmas
ALDO Jefry Chukka Boot (Men)
Current Price $150
Free Delivery by Christmas
Johnston & Murphy Larkin Chukka Boot (Men)
Current Price $99.99
Previous Price $159
Free Delivery by Christmas
BOSS Dresletic Suede Chukka Boot (Men) (Exclusive Retailer)
Current Price $399
Free Delivery by Christmas
Tod's Polacco Gomma Chukka Boot (Men)
Current Price $975
Free Delivery by Christmas
Clarks® Originals Wallabee Chukka Boot (Men)
Current Price $160
Free Delivery by Christmas
Josef Seibel Stuart Chukka (Men)
Current Price $175
Free Delivery by Christmas
Johnston & Murphy Parker Waterproof Chukka Boot (Men)
Current Price $129.99
Previous Price $189
Free Delivery by Christmas
SOREL Slabtown 62™ Stoic Chukka Boot (Men)
Current Price $160
Free Delivery by Christmas
Alden Last Chukka Boot (Men)
Current Price $694
Free Delivery by Christmas
Florsheim Forge Chukka Boot (Men)
Current Price $130
Free Delivery by Christmas
Mephisto Alexander Chukka Boot (Men)
Current Price $399
Free Delivery by Christmas
Eleventy Chukka Boot (Men)
Current Price $895
Free Delivery by Christmas
Tod's Apron Toe Suede Chukka Boot (Men)
Current Price $925
Free Delivery by Christmas
Sperry Mini Lug Chukka Boot (Men)
Current Price $150
Free Delivery by Christmas
Steve Madden Harros Chukka (Men)
Current Price $100
Free Delivery by Christmas
Ron White Larrado Weatherproof Chukka Boot (Men)
Current Price $565
Free Delivery by Christmas
Brunello Cucinelli Chukka Boot (Men)
Current Price $1,250
Free Delivery by Christmas
Dune London Maxxy Plain Toe Chukka Boot (Men)
Current Price $195
Free Delivery by Christmas
Dune London Smoky Plain Toe Chukka Boot (Men)
Current Price $195
Free Delivery by Christmas
Timberland Premium Waterproof Lace-Up Chukka Boot (Men)
Current Price $140 to $150
Free Delivery by Christmas
Børn 'Harrison' Chukka Boot (Online Only) (Men)
Current Price $145
Free Delivery by Christmas
Polo Ralph Lauren Asher Chukka (Men)
Current Price $198
Free Delivery by Christmas
Warfield & Grand Husky Chukka Boot (Men)
Current Price $179
Only a few left
Free Delivery by Christmas
Clarks® Originals Wallabee Scout Chukka Boot (Men)
Current Price $270 to $290
Free Delivery by Christmas
V.GAN LONDON Vegan Goji 2 Chukka Boots
Current Price $105
Previous Price $140
Free Delivery by Christmas
Florsheim Rucci Plain Toe Chukka Boot
Current Price $155
Free Delivery by Christmas
TO BOOT NEW YORK Monaco Plain Toe Chukka Boot (Men)
Current Price $425
Free Delivery by Christmas
Florsheim Launch Plain Toe Chukka (Men)
Current Price $135