Free Delivery by Christmas
Cole Haan Roundhill Grand Waterproof Chukka Boot (Men)
Current Price $260
Men's Comfort Boots
Free Delivery by Christmas
Johnston & Murphy Upton Chukka (Men)
Current Price $179
Free Delivery by Christmas
ECCO Metropole London Waterproof Suede Chukka Boot (Men)
Current Price $229.95
Free Delivery by Christmas
Rockport Flynn Plain Toe Derby Boot (Men)
Current Price $160
Free Delivery by Christmas
UGG® Neumel Era Chukka Boot (Men)
Current Price $159.95
Free Delivery by Christmas
Mephisto Leonardo HydroProtect Waterproof Genuine Shearling Lined Boot (Men)
Current Price $469
Free Delivery by Christmas
Blundstone Footwear Classic Chelsea Boot (Men)
Current Price $209.95 to $219.95
Free Delivery by Christmas
Børn Nigel Low Boot (Men)
Current Price $150
Free Delivery by Christmas
Johnston & Murphy Calder Oiled Suede Chukka Boot (Men)
Current Price $179
Free Delivery by Christmas
Johnston & Murphy Calder Plain Toe Chelsea Boot (Men)
Current Price $179
Free Delivery by Christmas
Josef Seibel Earl 04 Chukka Boot (Men)
Current Price $180
Free Delivery by Christmas
Johnston & Murphy Calder Chukka Boot (Men)
Current Price $179
Free Delivery by Christmas
Mephisto Berto Chukka Boot (Men)
Current Price $439
Free Delivery by Christmas
Ariat Rambler Boot (Men)
Current Price $189.95
Free Delivery by Christmas
Florsheim Traveler Chukka Boot (Men)
Current Price $135
Free Delivery by Christmas
Johnston & Murphy Durham Waterproof Cap Toe Boot (Men)
Current Price $199 to $229
Free Delivery by Christmas
Timberland Premium Waterproof Lace-Up Chukka Boot (Men)
Current Price $140 to $150
Free Delivery by Christmas
Timberland Redwood Falls Waterproof Lace-Up Boot (Men)
Current Price $160
Free Delivery by Christmas
Ariat Midtown Rambler Mid Chelsea Boot (Men)
Current Price $169.95
Free Delivery by Christmas
Johnston & Murphy Barret Zip Boot (Men)
Current Price $199
Free Delivery by Christmas
Børn Nigel Low Boot (Men)
Current Price $150
Free Delivery by Christmas
Vionic Uptown Jackson Boot - Wide Width Available (Men)
Current Price $230
Free Delivery by Christmas
Johnston & Murphy Upton Chukka (Men)
Current Price $179
Free Delivery by Christmas
Cole Haan Judson Grand Chelsea Boot (Men)
Current Price $260
Free Delivery by Christmas
Nordstrom Italian Collection Saluzzo Chukka Boot (Men)
Current Price $229.95
Free Delivery by Christmas
UGG® Idyllwild Lace-Up Boot (Men)
Current Price $189.95
Free Delivery by Christmas
Rockport Cassius Chelsea Boot (Men)
Current Price $160
Free Delivery by Christmas
Ariat Hilo Moc Toe Slip-On (Men)
Current Price $89.95
Free Delivery by Christmas
Børn Reed Zip-Up Boot (Men)
Current Price $150
Free Delivery by Christmas
Blundstone Footwear Thermal Waterproof Genuine Shearling Lined Chelsea Boot (Men)
Current Price $274.95
Free Delivery by Christmas
Florsheim Anthem Plain Toe Chukka (Men)
Current Price $145
Free Delivery by Christmas
Clarks® Originals Clarks® Desert Chukka Boot (Men)
Current Price $150
Free Delivery by Christmas
PIKOLINOS York M2M Lace-Up Cap Toe Boot (Men)
Current Price $240
Free Delivery by Christmas
Timberland Mid Lace-Up Moc Toe GORE-TEX® Shoe (Men)
Current Price $160
Free Delivery by Christmas
Johnston & Murphy Upton Chelsea Boot (Men)
Current Price $179
Free Delivery by Christmas
Aquatalia Golliard Water Resistant Chukka Boot (Men)
Current Price $495
Free Delivery by Christmas
Florsheim Forge Chukka Boot (Men)
Current Price $130
Free Delivery by Christmas
Josef Seibel Erroll Waterproof Chukka (Men)
Current Price $185
Free Delivery by Christmas
Ariat Slingshot Square Toe Cowboy Boot (Men)
Current Price $229.95 to $239.95
Free Delivery by Christmas
Red Wing 1907 Classic Moc Boot (Men)
Current Price $349.99
Free Delivery by Christmas
Johnston & Murphy XC Flex Connelly Wingtip Boot (Men)
Current Price $129.99 to $219
Previous Price $199 to $219
Free Delivery by Christmas
Ariat Sport Herdsman Square Toe Cowboy Boot (Men)
Current Price $189.95
Free Delivery by Christmas
Johnston & Murphy Upton Chelsea Boot (Men)
Current Price $179
Free Delivery by Christmas
UGG® Neumel Chukka Boot (Men)
Current Price $149.95
Free Delivery by Christmas
Ariat Sport Rambler Western Boot (Men)
Current Price $179.95
Free Delivery by Christmas
Timberland Premium 6-Inch Waterproof Boot (Men)
Current Price $198
Free Delivery by Christmas
Nordstrom Elijah Polished Leather Chelsea Boot (Men)
Current Price $149.95
Free Delivery by Christmas
Aquatalia Bernardo Water Repellent Combat Boot (Men)
Current Price $495
Free Delivery by Christmas
Red Wing 6 Inch Moc Toe Boot
Current Price $319.99
Free Delivery by Christmas
Vionic Danfield Desert Boot (Men)
Current Price $210
Free Delivery by Christmas
Florsheim Anthem Plain Toe Chelsea Boot (Men)
Current Price $145
Free Delivery by Christmas
Johnston & Murphy Calder Chelsea Boot (Men)
Current Price $179
Free Delivery by Christmas
Johnston & Murphy Braxton Chukka Boot (Men)
Current Price $159
Free Delivery by Christmas
Timberland Redwood Falls Chelsea Boot (Men)
Current Price $130
Free Delivery by Christmas
OluKai Mōlina Water Repellent Boot (Men)
Current Price $150
Free Delivery by Christmas
Timberland Oak Forge Boot (Men)
Current Price $225
Free Delivery by Christmas
Ariat Booker Ultra Square Toe Western Chelsea Boot (Men)
Current Price $149.95
Free Delivery by Christmas
Red Wing 6 Inch Moc Toe Boot
Current Price $319.99 to $329.99
Free Delivery by Christmas
ECCO Track 25 Waterproof Boot (Men)
Current Price $274.95
Free Delivery by Christmas
Ariat Booker Ultra Chelsea Boot (Men)
Current Price $149.95
Free Delivery by Christmas
Ariat Hybrid Low Boy Western Chelsea Boot (Men)
Current Price $159.95
Free Delivery by Christmas
ECCO Metropole Milan Chelsea Boot (Men)
Current Price $194.95
Free Delivery by Christmas
Børn Erik Lace-Up Boot (Men)
Current Price $160
Free Delivery by Christmas
Johnston & Murphy Parker Waterproof Chukka Boot (Men)
Current Price $189
Free Delivery by Christmas
Vionic Livermore Water Repellent Lace-Up Bootie (Men)
Current Price $210 to $230
Free Delivery by Christmas
Red Wing Blacksmith Boot (Men)
Current Price $329.99
Free Delivery by Christmas
Blundstone Footwear Classic 587 Water Resistant Chelsea Boot (Men)
Current Price $209.95
Free Delivery by Christmas
Clarks® Wallabee Suede Boot (Men)
Current Price $120
Free Delivery by Christmas
Josef Seibel Stuart Chukka (Men)
Current Price $175
Free Delivery by Christmas
Johnston & Murphy Reeve Chelsea Boot (Men)
Current Price $139
Free Delivery by Christmas
Ariat 'Heritage' Leather Cowboy R-Toe Boot (Men)
Current Price $199.95