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Men's Comfort Boots

Roundhill Grand Waterproof Chukka Boot (Men)

Free Delivery by Christmas

Cole Haan Roundhill Grand Waterproof Chukka Boot (Men)

Current Price $260

Golliard Water Resistant Chukka Boot (Men)

Free Delivery by Christmas

Aquatalia Golliard Water Resistant Chukka Boot (Men)

Current Price $495

Classic 587 Water Resistant Chelsea Boot (Men)

Free Delivery by Christmas

Blundstone Footwear Classic 587 Water Resistant Chelsea Boot (Men)

Current Price $209.95

Bernardo Water Repellent Combat Boot (Men)

Free Delivery by Christmas

Aquatalia Bernardo Water Repellent Combat Boot (Men)

Current Price $495

Prospero Water Resistant Chelsea Boot (Men)

Free Delivery by Christmas

Aquatalia Prospero Water Resistant Chelsea Boot (Men)

Current Price $450

Barret Zip Boot (Men)

Free Delivery by Christmas

Johnston & Murphy Barret Zip Boot (Men)

Current Price $199

Classic Chelsea Boot (Men)

Free Delivery by Christmas

Blundstone Footwear Classic Chelsea Boot (Men)

Current Price $209.95 to $219.95

Erroll Waterproof Chukka (Men)

Free Delivery by Christmas

Josef Seibel Erroll Waterproof Chukka (Men)

Current Price $185

Calder Chukka Boot (Men)

Free Delivery by Christmas

Johnston & Murphy Calder Chukka Boot (Men)

Current Price $179

Upton Chukka (Men)

Free Delivery by Christmas

Johnston & Murphy Upton Chukka (Men)

Current Price $119.99

Previous Price $179

Berto Chukka Boot (Men)

Free Delivery by Christmas

Mephisto Berto Chukka Boot (Men)

Current Price $439

Redwood Falls Waterproof Lace-Up Boot (Men)

Free Delivery by Christmas

Timberland Redwood Falls Waterproof Lace-Up Boot (Men)

Current Price $160

Leonardo HydroProtect Waterproof Genuine Shearling Lined Boot (Men)

Free Delivery by Christmas

Mephisto Leonardo HydroProtect Waterproof Genuine Shearling Lined Boot (Men)

Current Price $469

6-Inch Premium Waterproof Boot (Men)

Free Delivery by Christmas

Timberland 6-Inch Premium Waterproof Boot (Men)

Current Price $198

Durham Waterproof Cap Toe Boot (Men)

Free Delivery by Christmas

Johnston & Murphy Durham Waterproof Cap Toe Boot (Men)

Current Price $199 to $229

Water Resistant Chelsea Boot (Men)

Free Delivery by Christmas

Blundstone Footwear Water Resistant Chelsea Boot (Men)

Current Price $209.95

Danny Water Resistant Lace-Up Boot (Men)

Free Delivery by Christmas

Aquatalia Danny Water Resistant Lace-Up Boot (Men)

Current Price $550

Thermal All Terrain Water Resistant Chelsea Boot (Men)

Free Delivery by Christmas

Blundstone Footwear Thermal All Terrain Water Resistant Chelsea Boot (Men)

Current Price $274.95

Classic Mini Boot (Men)

Free Delivery by Christmas

UGG® Classic Mini Boot (Men)

Current Price $169.95

Water Resistant Lace-Up Boot (Men)

Free Delivery by Christmas

Blundstone Footwear Water Resistant Lace-Up Boot (Men)

Current Price $234.95

Blacksmith Boot (Men)

Free Delivery by Christmas

Red Wing Blacksmith Boot (Men)

Current Price $329.99

Earl 04 Chukka Boot (Men)

Free Delivery by Christmas

Josef Seibel Earl 04 Chukka Boot (Men)

Current Price $180

Clarks® Desert Chukka Boot (Men)

Free Delivery by Christmas

Clarks® Originals Clarks® Desert Chukka Boot (Men)

Current Price $150

Pitt Mid Lace-Up Boot (Men)

Free Delivery by Christmas

Mephisto Pitt Mid Lace-Up Boot (Men)

Current Price $499

Neumel Era Chukka Boot (Men)

Free Delivery by Christmas

UGG® Neumel Era Chukka Boot (Men)

Current Price $119.96

Previous Price $159.95

Track 25 Waterproof Boot (Men)

Free Delivery by Christmas

ECCO Track 25 Waterproof Boot (Men)

Current Price $274.95

Italian Collection Saluzzo Chukka Boot (Men)

Free Delivery by Christmas

Nordstrom Italian Collection Saluzzo Chukka Boot (Men)

Current Price $229.95

Thermal Waterproof Genuine Shearling Lined Chelsea Boot (Men)

Free Delivery by Christmas

Blundstone Footwear Thermal Waterproof Genuine Shearling Lined Chelsea Boot (Men)

Current Price $274.95

Fero 2.0 Waterproof Ankle Boot (Men)

Free Delivery by Christmas

Pajar Fero 2.0 Waterproof Ankle Boot (Men)

Current Price $195

Denali Water Resistant Lace-Up Boot (Men)

Free Delivery by Christmas

Aquatalia Denali Water Resistant Lace-Up Boot (Men)

Current Price $550

Metropole London Waterproof Suede Chukka Boot (Men)

Free Delivery by Christmas

ECCO Metropole London Waterproof Suede Chukka Boot (Men)

Current Price $229.95

Idyllwild Lace-Up Boot (Men)

Free Delivery by Christmas

UGG® Idyllwild Lace-Up Boot (Men)

Current Price $189.95

Judson Grand Chelsea Boot (Men)

Free Delivery by Christmas

Cole Haan Judson Grand Chelsea Boot (Men)

Current Price $260

Barrett Plain Toe Boot (Men)

Free Delivery by Christmas

Johnston & Murphy Barrett Plain Toe Boot (Men)

Current Price $199

Brutus Boot (Men)

Free Delivery by Christmas

Camper Brutus Boot (Men)

Current Price $230

Neumel Chukka Boot (Men)

Free Delivery by Christmas

UGG® Neumel Chukka Boot (Men)

Current Price $149.95

Blundstone City Chelsea Boot (Men)

Free Delivery by Christmas

Blundstone Footwear Blundstone City Chelsea Boot (Men)

Current Price $224.95 to $234.95

Adirondack XXV Boot (Men)

Free Delivery by Christmas

UGG® Adirondack XXV Boot (Men)

Current Price $249.95

Reed Zip-Up Boot (Men)

Free Delivery by Christmas

Børn Reed Zip-Up Boot (Men)

Current Price $150

Calder Oiled Suede Chukka Boot (Men)

Free Delivery by Christmas

Johnston & Murphy Calder Oiled Suede Chukka Boot (Men)

Current Price $179

Moab 3 Mid Waterproof Hiking Shoe (Men)

Free Delivery by Christmas

Merrell Moab 3 Mid Waterproof Hiking Shoe (Men)

Current Price $170

Cassius Chelsea Boot (Men)

Free Delivery by Christmas

Rockport Cassius Chelsea Boot (Men)

Current Price $160

Arcata Waterproof Boot (Men)

Free Delivery by Christmas

Bogs Arcata Waterproof Boot (Men)

Current Price $180

Only a few left

Muir Waterproof Moc Toe Boot (Men)

Free Delivery by Christmas

Cole Haan Muir Waterproof Moc Toe Boot (Men)

Current Price $208

Mil 1913 Boot (Men)

Free Delivery by Christmas

Camper Mil 1913 Boot (Men)

Current Price $168

Previous Price $205

Judson Grand Chelsea Boot (Men)

Free Delivery by Christmas

Cole Haan Judson Grand Chelsea Boot (Men)

Current Price $260

Metropole Milan Chelsea Boot (Men)

Free Delivery by Christmas

ECCO Metropole Milan Chelsea Boot (Men)

Current Price $194.95

Redwood Falls Waterproof Boot (Men)

Free Delivery by Christmas

Timberland Redwood Falls Waterproof Boot (Men)

Current Price $145

Only a few left

Uptown Jackson Boot - Wide Width Available (Men)

Free Delivery by Christmas

Vionic Uptown Jackson Boot - Wide Width Available (Men)

Current Price $230

1907 Classic Moc Boot (Men)

Free Delivery by Christmas

Red Wing 1907 Classic Moc Boot (Men)

Current Price $349.99

Braxton Chukka Boot (Men)

Free Delivery by Christmas

Johnston & Murphy Braxton Chukka Boot (Men)

Current Price $159

Stuart Chukka (Men)

Free Delivery by Christmas

Josef Seibel Stuart Chukka (Men)

Current Price $175

Plain Toe Chelsea Boot (Men)

Free Delivery by Christmas

Blundstone Footwear Plain Toe Chelsea Boot (Men)

Current Price $209.95

Nigel Low Boot (Men)

Free Delivery by Christmas

Børn Nigel Low Boot (Men)

Current Price $150

Moab Speed 2 Gore-Tex® Mid Hiking Shoe (Men)

Free Delivery by Christmas

Merrell Moab Speed 2 Gore-Tex® Mid Hiking Shoe (Men)

Current Price $180

Classic Chelsea Boot (Men)

Free Delivery by Christmas

Blundstone Footwear Classic Chelsea Boot (Men)

Current Price $219.95

Ultra Mini Classic Water Resistant Boot (Men)

Free Delivery by Christmas

UGG® Ultra Mini Classic Water Resistant Boot (Men)

Current Price $159.95

Erik Lace-Up Boot (Men)

Free Delivery by Christmas

Børn Erik Lace-Up Boot (Men)

Current Price $160

Arcata Boot (Men)

Free Delivery by Christmas

Bogs Arcata Boot (Men)

Current Price $180

Premium Waterproof Lace-Up Chukka Boot (Men)

Free Delivery by Christmas

Timberland Premium Waterproof Lace-Up Chukka Boot (Men)

Current Price $140 to $150

Alexander Chukka Boot (Men)

Free Delivery by Christmas

Mephisto Alexander Chukka Boot (Men)

Current Price $399

Kicker II Waterproof Chelsea Rain Boot (Men)

Free Delivery by Christmas

Bogs Kicker II Waterproof Chelsea Rain Boot (Men)

Current Price $95

Nigel Low Boot (Men)

Free Delivery by Christmas

Børn Nigel Low Boot (Men)

Current Price $150

Highwood Mid Lace-Up Boot (Men)

Free Delivery by Christmas

Birkenstock Highwood Mid Lace-Up Boot (Men)

Current Price $209.95

Classic Seamles Mid Waterproof Boot (Men)

Free Delivery by Christmas

Bogs Classic Seamles Mid Waterproof Boot (Men)

Current Price $140

Original Water Resistant Chelsea Boot (Men)

Free Delivery by Christmas

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

Current Price $199.95

Calder Plain Toe Chelsea Boot (Men)

Free Delivery by Christmas

Johnston & Murphy Calder Plain Toe Chelsea Boot (Men)

Current Price $179

Mōlina Water Repellent Boot (Men)

Free Delivery by Christmas

OluKai Mōlina Water Repellent Boot (Men)

Current Price $150

Chelsea Lug Boot (Men)

Free Delivery by Christmas

UGG® Chelsea Lug Boot (Men)

Current Price $159.95

Fenwick Waterproof Boot (Men)

Free Delivery by Christmas

Pajar Fenwick Waterproof Boot (Men)

Current Price $190

Anthem Plain Toe Chelsea Boot (Men)

Free Delivery by Christmas

Florsheim Anthem Plain Toe Chelsea Boot (Men)

Current Price $145