Men's Comfort Boots

New Markdown

Johnston & Murphy Upton Chukka (Men)

$119.99Current Price $119.99

$179Previous Price $179

New!

UGG® Neumel Chukka Boot (Men)

$149.95Current Price $149.95

Cole Haan Roundhill Grand Waterproof Chukka Boot (Men)

$260Current Price $260

New Markdown

Johnston & Murphy Parker Waterproof Chukka Boot (Men)

$129.99Current Price $129.99

$189Previous Price $189

Ariat Hilo Moc Toe Slip-On (Men)

$89.95Current Price $89.95

UGG® Neumel Era Chukka Boot (Men)

$159.95Current Price $159.95

Ariat Sport Rambler Western Boot (Men)

$179.95Current Price $179.95

Blundstone Footwear Classic Chelsea Boot (Men)

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

UGG® Classic Ultra Mini Regen Boot (Men)

$109.99Current Price $109.99

$169.95Previous Price $169.95

Blundstone Footwear Classic 587 Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

UGG® Chelsea Lug Boot (Men)

$89.96Current Price $89.96

$149.95Previous Price $149.95

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Get it by Christmas

UGG® Idyllwild Lace-Up Boot (Men)

$189.95Current Price $189.95

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

Ariat Hybrid Low Boy Western Chelsea Boot (Men)

$159.95Current Price $159.95

Johnston & Murphy Barret Zip Boot (Men)

$199Current Price $199

Timberland 6-Inch Premium Waterproof Boot (Men)

$199Current Price $199

New!

Ariat Wexford Waterproof Chelsea Boot (Men)

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

Ariat Sport Wide Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

Ariat Midtown Rambler Mid Chelsea Boot (Men)

$169.95Current Price $169.95

Florsheim Forge Chukka Boot (Men)

$130Current Price $130

New!

Ariat Sport Outdoor Square Toe Cowboy Boot (Men)

$169.95 – $179.95Current Price $169.95 to $179.95

Johnston & Murphy Durham Waterproof Cap Toe Boot (Men)

$199 – $229Current Price $199 to $229

UGG® Neumel Chelsea Boot (Men)

$149.95Current Price $149.95

Ariat Sport Herdsman Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

Ariat Sport Rambler Western Boot (Men)

$179.95Current Price $179.95

UGG® Classic Mini Boot (Men)

$169.95Current Price $169.95

Vionic Uptown Jackson Boot - Wide Width Available (Men)

$230Current Price $230

New Markdown

Johnston & Murphy Upton Chelsea Boot (Men)

$119.99Current Price $119.99

$179Previous Price $179

Rockport Cassius Chelsea Boot (Men)

$160Current Price $160

Ariat Booker Ultra Chelsea Boot (Men)

$149.95Current Price $149.95

Cole Haan Muir Waterproof Moc Toe Boot (Men)

$208Current Price $208

Timberland Premium Waterproof Lace-Up Chukka Boot (Men)

$140 – $150Current Price $140 to $150

Get it by Christmas

Timberland Oak Forge Boot (Men)

$225Current Price $225

UGG® Chukka Lug Boot (Men)

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

$149.95Previous Price $149.95

Børn Reed Zip-Up Boot (Men)

$150Current Price $150

Get it by Christmas

Johnston & Murphy Larkin Chukka Boot (Men)

$99.99Current Price $99.99

$159Previous Price $159

Blundstone Footwear Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

Get it by Christmas

Nordstrom Italian Collection Saluzzo Chukka Boot (Men)

$229.95Current Price $229.95

Timberland White Ledge Waterproof Hiking Boot (Men)

$120Current Price $120

UGG® Ultra Mini Classic Water Resistant Boot (Men)

$159.95Current Price $159.95

New Markdown

ECCO Metropole Milan Chelsea Boot (Men)

$137.50Current Price $137.50

$194.95Previous Price $194.95

Johnston & Murphy Braxton Chukka Boot (Men)

$159Current Price $159

Ariat Sport Herdsman Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

Johnston & Murphy Reeve Chelsea Boot (Men)

$139Current Price $139

New!

Clarks® Originals Wallabee Kiltie Chukka Boot (Men)

$170 – $190Current Price $170 to $190

Ariat Sport Big Country Wide Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

Ariat Sport Cool VentTEK™ Cowboy Boot (Men)

$199.95Current Price $199.95

Timberland Redwood Falls Waterproof Lace-Up Boot (Men)

$160Current Price $160

Florsheim Forge Chelsea Boot (Men)

$130Current Price $130

New Markdown

Camper Chasis Sport Boot (Men)

$133Current Price $133

$185Previous Price $185

Minnetonka Torrey Berber Fleece Lined Slipper Boot (Men)

$89.95Current Price $89.95

OluKai Mōlina Water Repellent Boot (Men)

$150Current Price $150

Ariat Sport Freedom Western Boot (Men)

$169.95Current Price $169.95

Florsheim Anthem Plain Toe Chelsea Boot (Men)

$145Current Price $145

Ariat Rambler Boot (Men)

$189.95Current Price $189.95

Birkenstock Highwood Chelsea Boot (Men)

$209.95Current Price $209.95

Børn Nigel Low Boot (Men)

$150Current Price $150

Timberland Redwood Falls Chelsea Boot (Men)

$130Current Price $130

Ariat Circuit Patriot Cowboy Boot (Men)

$209.95Current Price $209.95

New Markdown

Johnston & Murphy XC Flex Connelly Lace-Up Leather Boot (Men)

$149.99Current Price $149.99

$199Previous Price $199

Timberland Field Waterproof Boot (Men)

$160Current Price $160

UGG® Classic Ultra Mini Genuine Shearling Boot (Men)

$99.99Current Price $99.99

$159.95Previous Price $159.95

New!

Ariat Big Sport Cowboy Boot (Men)

$179.95Current Price $179.95

Ariat Slingshot Square Toe Cowboy Boot (Men)

$229.95 – $239.95Current Price $229.95 to $239.95

Johnston & Murphy Calder Plain Toe Chelsea Boot (Men)

$179Current Price $179

Rockport Flynn Plain Toe Derby Boot (Men)

$160Current Price $160

Ariat Oakwood Cowboy Boot (Men)

$259.95Current Price $259.95

UGG® Truckee Field Boot (Men)

$149.95Current Price $149.95

Florsheim Anthem Plain Toe Chukka (Men)

$145Current Price $145

Børn Nigel Low Boot (Men)

$150Current Price $150

Johnston & Murphy Calder Chukka Boot (Men)

$179Current Price $179