Men's Comfort Boots

Blundstone Footwear Classic Chelsea Boot (Men)

$209.95 – $219.95Current Price $209.95 to $219.95

Johnston & Murphy Upton Chukka (Men)

$119.99Current Price $119.99

$179Previous Price $179

Cole Haan Roundhill Grand Waterproof Chukka Boot (Men)

$260Current Price $260

ECCO Metropole London Waterproof Suede Chukka Boot (Men)

$159.99 – $172.50Current Price $159.99 to $172.50

$229.95Previous Price $229.95

Johnston & Murphy Parker Waterproof Chukka Boot (Men)

$129.99Current Price $129.99

$189Previous Price $189

UGG® Neumel Chukka Boot (Men)

$149.95Current Price $149.95

UGG® Neumel Era Chukka Boot (Men)

$159.95Current Price $159.95

ECCO Metropole Milan Chelsea Boot (Men)

$137.50Current Price $137.50

$194.95Previous Price $194.95

Blundstone Footwear Classic 587 Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

UGG® Classic Mini Boot (Men)

$169.95Current Price $169.95

UGG® Ultra Mini Classic Water Resistant Boot (Men)

$159.95Current Price $159.95

Clarks® Originals Clarks® Desert Chukka Boot (Men)

$150Current Price $150

Johnston & Murphy Larkin Chukka Boot (Men)

$99.99Current Price $99.99

$159Previous Price $159

New Markdown

Birkenstock Highwood Chelsea Boot (Men)

$124.99 – $137.50Current Price $124.99 to $137.50

$209.95Previous Price $209.95

Josef Seibel Erroll Waterproof Chukka (Men)

$185Current Price $185

Blundstone Footwear Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

Rockport Cassius Chelsea Boot (Men)

$160Current Price $160

Johnston & Murphy Barret Zip Boot (Men)

$199Current Price $199

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$184.95Current Price $184.95

Mephisto Berto Chukka Boot (Men)

$439Current Price $439

Blundstone Footwear Blundstone City Chelsea Boot (Men)

$224.95 – $234.95Current Price $224.95 to $234.95

Nordstrom Italian Collection Saluzzo Chukka Boot (Men)

$229.95Current Price $229.95

Nordstrom Elijah Polished Leather Chelsea Boot (Men)

$149.95Current Price $149.95

Johnston & Murphy Calder Chukka Boot (Men)

$179Current Price $179

Timberland 6-Inch Premium Waterproof Boot (Men)

$199Current Price $199

Johnston & Murphy Calder Plain Toe Chelsea Boot (Men)

$179Current Price $179

UGG® Chelsea Lug Boot (Men)

$89.96Current Price $89.96

$149.95Previous Price $149.95

Merrell Thermo Chill 2 Waterproof Boot (Men)

$150Current Price $150

Camper Dean Chelsea Boot (Men)

$185.50 – $245Current Price $185.50 to $245

$245 – $260Previous Price $245 to $260

Johnston & Murphy Upton Chelsea Boot (Men)

$119.99Current Price $119.99

$179Previous Price $179

New!

Aquatalia Golliard Water Resistant Chukka Boot (Men)

$495Current Price $495

Clarks® Originals Desert Boot (Men)

$160Current Price $160

Clarks® Originals Clarks® Desert Trek Chukka Boot (Men)

$140 – $150Current Price $140 to $150

Rockport Flynn Plain Toe Derby Boot (Men)

$160Current Price $160

Clarks® Originals Wallabee Chukka (Men)

$160Current Price $160

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$199.95Current Price $199.95

Blundstone Footwear Water Resistant Classics Chelsea Boot (Men)

$209.95Current Price $209.95

UGG® Idyllwild Lace-Up Boot (Men)

$189.95Current Price $189.95

Josef Seibel Earl 04 Chukka Boot (Men)

$180Current Price $180

Vionic Uptown Jackson Boot - Wide Width Available (Men)

$230Current Price $230

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

$239.95Current Price $239.95

Johnston & Murphy Braxton Chukka Boot (Men)

$159Current Price $159

Bogs Digger Waterproof Boot (Men)

$95Current Price $95

Clarks® Originals Wallabee Chukka Boot (Men)

$160 – $170Current Price $160 to $170

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

$274.95Current Price $274.95

Cole Haan Judson Grand Chelsea Boot (Men)

$260Current Price $260

Aquatalia Bernardo Water Repellent Combat Boot (Men)

$495Current Price $495

Timberland Mid Lace-Up Moc Toe GORE-TEX® Shoe (Men)

$160Current Price $160

Red Wing 1907 Classic Moc Boot (Men)

$349.99Current Price $349.99

Camper Norman Ankle Boot (Men)

$147 – $205Current Price $147 to $205

$205Previous Price $205

Børn Nigel Low Boot (Men)

$150Current Price $150

Blundstone Footwear Plain Toe Chelsea Boot (Men)

$209.95Current Price $209.95

UGG® Chelsea Lug Boot (Men)

$159.95Current Price $159.95

Bogs Digger Waterproof Clog (Men)

$80Current Price $80

Cole Haan Judson Grand Chelsea Boot (Men)

$260Current Price $260

New!

Ariat Wexford Waterproof Chelsea Boot (Men)

$189.95 – $199.95Current Price $189.95 to $199.95

New Markdown

UGG® Neumel Waterproof Hybrid Boot (Men)

$142.50 – $189.95Current Price $142.50 to $189.95

$189.95Previous Price $189.95

UGG® Classic Ultra Mini Regen Boot (Men)

$109.99Current Price $109.99

$169.95Previous Price $169.95

Only a few left

Camper Chasis Sport Boot (Men)

$133Current Price $133

$185Previous Price $185

Børn 'Harrison' Chukka Boot (Online Only) (Men)

$145Current Price $145

Ariat Sport Rambler Western Boot (Men)

$179.95Current Price $179.95

Johnston & Murphy Calder Oiled Suede Chukka Boot (Men)

$179Current Price $179

Timberland Premium Waterproof Lace-Up Chukka Boot (Men)

$140 – $150Current Price $140 to $150

Ariat Sport Herdsman Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

Florsheim Traveler Chukka Boot (Men)

$135Current Price $135

Red Wing Iron Ranger Cap Toe Boot (Men)

$349.99Current Price $349.99

UGG® Neumel Chelsea Boot (Men)

$149.95Current Price $149.95

Johnston & Murphy Durham Waterproof Cap Toe Boot (Men)

$199 – $229Current Price $199 to $229

Johnston & Murphy Calder 175th Chukka Boot (Men)

$175Current Price $175

Florsheim Forge Chukka Boot (Men)

$130Current Price $130

New!

Blundstone Footwear Classic Chelsea Boot (Men)

$219.95Current Price $219.95