Men's Comfort Boots

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Timberland Premium 6-Inch Waterproof Boot (Men)

$199Current Price $199

Blundstone Footwear Classic Chelsea Boot (Men)

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

Birkenstock Highwood Chelsea Boot (Men)

$99.99 – $124.99Current Price $99.99 to $124.99

$209.95Previous Price $209.95

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ECCO Metropole Milan Chelsea Boot (Men)

$137.50Current Price $137.50

$194.95Previous Price $194.95

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$184.95Current Price $184.95

Blundstone Footwear Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

Børn Reed Zip-Up Boot (Men)

$97.50 – $112.50Current Price $97.50 to $112.50

$150Previous Price $150

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Cole Haan Judson Grand Chelsea Boot (Men)

$182Current Price $182

$260Previous Price $260

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ECCO Metropole London Waterproof Suede Chukka Boot (Men)

$119.98 – $159.99Current Price $119.98 to $159.99

$229.95Previous Price $229.95

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Cole Haan Judson Grand Chelsea Boot (Men)

$182Current Price $182

$260Previous Price $260

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Pajar Fero 2.0 Waterproof Ankle Boot (Men)

$146.25 – $195Current Price $146.25 to $195

$195Previous Price $195

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Johnston & Murphy Upton Chukka (Men)

$119.99Current Price $119.99

$179Previous Price $179

UGG® Chelsea Lug Boot (Men)

$95.96Current Price $95.96

$159.95Previous Price $159.95

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Blundstone Footwear Classic 587 Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

ECCO Offroad Waterproof Hiking Boot (Men)

$92.47Current Price $92.47

$184.95Previous Price $184.95

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Florsheim Anthem Plain Toe Chelsea Boot (Men)

$145Current Price $145

Red Wing 1907 Classic Moc Boot (Men)

$349.99Current Price $349.99

Blundstone Footwear Gender Inclusive Chelsea Boot

$209.95Current Price $209.95

Johnston & Murphy XC Flex Connelly Wingtip Boot (Men)

$149.99 – $199Current Price $149.99 to $199

$199 – $219Previous Price $199 to $219

Merrell Thermo Chill 2 Waterproof Boot (Men)

$150Current Price $150

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Merrell Moab 3 Mid Hiking Shoe (Men)

$150Current Price $150

Johnston & Murphy Barrett Plain Toe Boot (Men)

$139.29 – $199Current Price $139.29 to $199

$199Previous Price $199

Camper Dean Chelsea Boot (Men)

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

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

Timberland White Ledge Waterproof Hiking Boot (Men)

$120Current Price $120

Blundstone Footwear Plain Toe Chelsea Boot (Men)

$209.95Current Price $209.95

Johnston & Murphy Durham Waterproof Cap Toe Boot (Men)

$219Current Price $219

Timberland Redwood Falls Waterproof Lace-Up Boot (Men)

$160Current Price $160

Florsheim Traveler Chukka Boot (Men)

$135Current Price $135

Rockport Cassius Chelsea Boot (Men)

$160Current Price $160

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Ariat Bodie Western Boot (Men)

$179.95Current Price $179.95

Camper Dean Chelsea Boot (Men)

$175Current Price $175

$245Previous Price $245

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

$274.95Current Price $274.95

Birkenstock Highwood Mid Lace-Up Boot (Men)

$134.99Current Price $134.99

$209.95Previous Price $209.95

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Ariat Booker Wide Square Toe Western Chelsea Boot (Men)

$149.95Current Price $149.95

Clarks® Originals Clarks® Desert Chukka Boot (Men)

$140 – $150Current Price $140 to $150

Ariat Booker Ultra Chelsea Boot (Men)

$149.95Current Price $149.95

UGG® Chelsea Lug Boot (Men)

$74.99Current Price $74.99

$149.95Previous Price $149.95

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Johnston & Murphy Barret Zip Boot (Men)

$199Current Price $199

UGG® Classic Mini Boot (Men)

$169.95Current Price $169.95

Mephisto Alexander Chukka Boot (Men)

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Florsheim Anthem Plain Toe Chukka (Men)

$145Current Price $145

Camper Mil 1913 Boot (Men)

$157.50Current Price $157.50

$205Previous Price $205

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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

Red Wing 6 Inch Moc Toe Boot

$319.99 – $329.99Current Price $319.99 to $329.99

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

$239.95Current Price $239.95

ECCO Track 25 Waterproof Boot (Men)

$274.95Current Price $274.95

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Rockport Flynn Plain Toe Derby Boot (Men)

$160Current Price $160

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

$149.99Current Price $149.99

$199Previous Price $199

Blundstone Footwear Gender Inclusive Blundstone Original Series Chelsea Boot

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

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

$274.95Current Price $274.95

UGG® Classic Ultra Mini Weather Hybrid Boot (Men)

$149.96 – $199.95Current Price $149.96 to $199.95

$199.95Previous Price $199.95

Aquatalia Bernardo Water Repellent Combat Boot (Men)

$495Current Price $495

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$199.95Current Price $199.95

Florsheim 'Midtown' Zip Boot (Men)

$150Current Price $150

Blundstone Footwear Water Resistant Chelsea Boot (Men)

$184.95Current Price $184.95

UGG® Classic Ultra Mini Genuine Shearling Boot (Men)

$99.99Current Price $99.99

$159.95Previous Price $159.95

Camper Pix Berlin Zip Boot (Men)

$196Current Price $196

$265Previous Price $265

UGG® Classic Ultra Mini Regen Boot (Men)

$84.96Current Price $84.96

$169.95Previous Price $169.95

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Samuel Hubbard Uptown Maverick Boot (Men)

$162.25Current Price $162.25

$295Previous Price $295

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UGG® Truckee Field Boot (Men)

$149.95Current Price $149.95

Timberland Earthkeepers® Original Mid Plain Toe Boot (Men)

$160Current Price $160

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Ariat Booker Wide Square Toe Western Chelsea Boot (Men)

$149.95Current Price $149.95

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

$99.99Current Price $99.99

$160Previous Price $160

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Nordstrom Lockhart Mini Lug Suede Chelsea Boot (Men)

$119.95Current Price $119.95

Timberland Mt. Maddsen Water Resistant Hiking Boot (Men)

$110Current Price $110

Cole Haan Roundhill Grand Waterproof Chukka Boot (Men)

$260Current Price $260

Johnston & Murphy Reeve Chelsea Boot (Men)

$139Current Price $139

Camper Brutus Boot (Men)

$192 – $235Current Price $192 to $235

$235Previous Price $235

Johnston & Murphy Larkin Chukka Boot (Men)

$99.99Current Price $99.99

$159Previous Price $159

UGG® Neumel Era Chukka Boot (Men)

$159.95Current Price $159.95