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

UGG® Neumel Chukka Boot (Men)

$98 – $149.95Current Price $98 to $149.95

$149.95Previous Price $149.95

New Markdown

Birkenstock Highwood Chelsea Boot (Men)

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

$209.95Previous Price $209.95

UGG® Neumel Era Chukka Boot (Men)

$159.95Current Price $159.95

UGG® Chelsea Lug Boot (Men)

$89.96Current Price $89.96

$149.95Previous Price $149.95

UGG® Classic Ultra Mini Regen Boot (Men)

$109.99Current Price $109.99

$169.95Previous Price $169.95

New Markdown

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® Chukka Lug Boot (Men)

$84.99 – $99.99Current Price $84.99 to $99.99

$149.95Previous Price $149.95

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Cole Haan Roundhill Grand Waterproof Chukka Boot (Men)

$260Current Price $260

New Markdown

ECCO Metropole Milan Chelsea Boot (Men)

$137.50Current Price $137.50

$194.95Previous Price $194.95

Blundstone Footwear Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

UGG® Classic Mini Boot (Men)

$169.95Current Price $169.95

Johnston & Murphy Larkin Chukka Boot (Men)

$99.99Current Price $99.99

$159Previous Price $159

Blundstone Footwear Classic 587 Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

New Markdown

UGG® Neumel Chelsea Boot (Men)

$112.50 – $149.95Current Price $112.50 to $149.95

$149.95Previous Price $149.95

UGG® Idyllwild Lace-Up Boot (Men)

$189.95Current Price $189.95

Camper Dean Chelsea Boot (Men)

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

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

Timberland 6-Inch Premium Waterproof Boot (Men)

$199Current Price $199

Camper Chasis Sport Boot (Men)

$133Current Price $133

$185Previous Price $185

Ariat Sport Rambler Western Boot (Men)

$179.95Current Price $179.95

Josef Seibel Erroll Waterproof Chukka (Men)

$185Current Price $185

Clarks® Originals Clarks® Desert Chukka Boot (Men)

$150Current Price $150

New Markdown

UGG® Neumel Waterproof Hybrid Boot (Men)

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

$189.95Previous Price $189.95

Johnston & Murphy Barret Zip Boot (Men)

$199Current Price $199

Rockport Cassius Chelsea Boot (Men)

$160Current Price $160

Ariat Hilo Moc Toe Slip-On (Men)

$89.95Current Price $89.95

Ariat Sport Herdsman Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

New!

Ariat Wexford Waterproof Chelsea Boot (Men)

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

Timberland Premium Waterproof Lace-Up Chukka Boot (Men)

$140 – $150Current Price $140 to $150

Nordstrom Elijah Polished Leather Chelsea Boot (Men)

$149.95Current Price $149.95

Blundstone Footwear Blundstone City Chelsea Boot (Men)

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

Florsheim Traveler Chukka Boot (Men)

$135Current Price $135

Clarks® Originals Desert Boot (Men)

$160Current Price $160

UGG® Classic Ultra Mini Genuine Shearling Boot (Men)

$99.99Current Price $99.99

$159.95Previous Price $159.95

Blundstone Footwear Gender Inclusive Blundstone Original Series Chelsea Boot

$179.95 – $184.95Current Price $179.95 to $184.95

New!

Blundstone Footwear Classic Chelsea Boot (Men)

$219.95Current Price $219.95

Timberland Premium 6-Inch Waterproof Boot (Men)

$198 – $210Current Price $198 to $210

UGG® Heritage Trailgazer Waterproof Genuine Shearling & Wool Boot (Men)

$134.99Current Price $134.99

$209.95Previous Price $209.95

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Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$184.95Current Price $184.95

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

$274.95Current Price $274.95

UGG® Chelsea Lug Boot (Men)

$159.95Current Price $159.95

Cole Haan Judson Grand Chelsea Boot (Men)

$260Current Price $260

Sperry Mini Lug Chukka Boot (Men)

$150Current Price $150

Ariat Sport Rambler Western Boot (Men)

$179.95Current Price $179.95

Børn Nigel Low Boot (Men)

$150Current Price $150

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$199.95Current Price $199.95

Ariat Sport Wide Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

Favorite Gift

Nordstrom Italian Collection Saluzzo Chukka Boot (Men)

$229.95Current Price $229.95

Clarks® Originals Wallabee Chukka Boot (Men)

$160 – $170Current Price $160 to $170

Johnston & Murphy Calder Plain Toe Chelsea Boot (Men)

$179Current Price $179

Camper Norman Ankle Boot (Men)

$147 – $205Current Price $147 to $205

$205Previous Price $205

UGG® Truckee Field Boot (Men)

$149.95Current Price $149.95

Bogs Kicker II Waterproof Chelsea Rain Boot (Men)

$95Current Price $95

Florsheim Forge Chukka Boot (Men)

$130Current Price $130

Timberland Redwood Falls Waterproof Lace-Up Boot (Men)

$160Current Price $160

Rockport Flynn Plain Toe Derby Boot (Men)

$160Current Price $160

Cole Haan Muir Waterproof Moc Toe Boot (Men)

$208Current Price $208

Josef Seibel Earl 04 Chukka Boot (Men)

$180Current Price $180

Camper Dean Desert Boot (Men)

$192Current Price $192

$235Previous Price $235

Camper Beetle Ankle Boot (Men)

$192Current Price $192

$235Previous Price $235

Ariat Sport Herdsman Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

Blundstone Footwear Water Resistant Classics Chelsea Boot (Men)

$209.95Current Price $209.95

UGG® Ultra Mini Classic Water Resistant Boot (Men)

$159.95Current Price $159.95

Bogs Digger Waterproof Clog (Men)

$80Current Price $80

Johnston & Murphy Durham Waterproof Cap Toe Boot (Men)

$199 – $229Current Price $199 to $229

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

$140 – $150Current Price $140 to $150

New!

Aquatalia Golliard Water Resistant Chukka Boot (Men)

$495Current Price $495

Merrell Thermo Chill 2 Waterproof Boot (Men)

$150Current Price $150

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

$145Current Price $145