Men's Comfort Boots

Johnston & Murphy Upton Chukka (Men)

$119.99Current Price $119.99

$179Previous Price $179

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

UGG® Neumel Era Chukka Boot (Men)

$159.95Current Price $159.95

Johnston & Murphy Parker Waterproof Chukka Boot (Men)

$129.99Current Price $129.99

$189Previous Price $189

New Markdown

Birkenstock Highwood Chelsea Boot (Men)

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

$209.95Previous Price $209.95

Johnston & Murphy Larkin Chukka Boot (Men)

$99.99Current Price $99.99

$159Previous Price $159

Timberland 6-Inch Premium Waterproof Boot (Men)

$199Current Price $199

UGG® Neumel Chukka Boot (Men)

$149.95Current Price $149.95

Blundstone Footwear Classic Chelsea Boot (Men)

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

ECCO Offroad Waterproof Hiking Boot (Men)

$120.21Current Price $120.21

$184.95Previous Price $184.95

New Markdown

ECCO Metropole Milan Chelsea Boot (Men)

$137.50Current Price $137.50

$194.95Previous Price $194.95

Timberland Field Waterproof Boot (Men)

$160Current Price $160

Johnston & Murphy Upton Chelsea Boot (Men)

$119.99Current Price $119.99

$179Previous Price $179

Ariat Sport Herdsman Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

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Timberland Oak Forge Boot (Men)

$225Current Price $225

Cole Haan Roundhill Grand Waterproof Chukka Boot (Men)

$260Current Price $260

PIKOLINOS Vigo Water Resistant Boot (Men)

$215Current Price $215

Børn Theo Chukka Boot (Men)

$97.50Current Price $97.50

$130Previous Price $130

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Merrell Thermo Chill 2 Waterproof Boot (Men)

$150Current Price $150

Blundstone Footwear Classic 587 Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

OluKai Mōlina Water Repellent Boot (Men)

$150Current Price $150

UGG® Chukka Lug Boot (Men)

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

$149.95Previous Price $149.95

Børn Nigel Low Boot (Men)

$150Current Price $150

Børn Nigel Low Boot (Men)

$150Current Price $150

Sperry Mini Lug Chukka Boot (Men)

$150Current Price $150

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UGG® Neumel Waterproof Hybrid Boot (Men)

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

$189.95Previous Price $189.95

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UGG® Neumel Chelsea Boot (Men)

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

$149.95Previous Price $149.95

Timberland Redwood Falls Waterproof Lace-Up Boot (Men)

$160Current Price $160

Timberland Mt. Maddsen Waterproof Hiking Boot (Men)

$120 – $125Current Price $120 to $125

Bogs Kicker II Waterproof Chelsea Rain Boot (Men)

$95Current Price $95

Ariat Hilo Moc Toe Slip-On (Men)

$89.95Current Price $89.95

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Camper Walden Chelsea Boot (Men)

$196Current Price $196

$275Previous Price $275

ECCO Track 25 Waterproof Boot (Men)

$274.95Current Price $274.95

Josef Seibel Erroll Waterproof Chukka (Men)

$185Current Price $185

Timberland Premium Waterproof Lace-Up Chukka Boot (Men)

$140 – $150Current Price $140 to $150

Timberland Mt. Maddsen Water Resistant Hiking Boot (Men)

$110Current Price $110

Rockport Cassius Chelsea Boot (Men)

$160Current Price $160

New!

Ariat Wexford Waterproof Chelsea Boot (Men)

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

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Camper Chasis Sport Boot (Men)

$133Current Price $133

$185Previous Price $185

Johnston & Murphy Barret Zip Boot (Men)

$199Current Price $199

Ariat Sport Herdsman Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

Timberland Earthkeepers® Original Mid Plain Toe Boot (Men)

$160Current Price $160

Johnston & Murphy Calder Oiled Suede Chukka Boot (Men)

$179Current Price $179

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

$274.95Current Price $274.95

Blundstone Footwear Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

New Markdown

Camper Pix Berlin Zip Boot (Men)

$196Current Price $196

$265Previous Price $265

Johnston & Murphy Braxton Chukka Boot (Men)

$159Current Price $159

Mephisto Leonardo HydroProtect Waterproof Genuine Shearling Lined Boot (Men)

$469Current Price $469

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$184.95Current Price $184.95

Ariat Sport Rambler Western Boot (Men)

$179.95Current Price $179.95

Johnston & Murphy Calder Chukka Boot (Men)

$179Current Price $179

Clarks® Originals Clarks® Desert Chukka Boot (Men)

$150Current Price $150

UGG® Truckee Field Boot (Men)

$149.95Current Price $149.95

Johnston & Murphy Durham Waterproof Cap Toe Boot (Men)

$199 – $229Current Price $199 to $229

Blundstone Footwear Gender Inclusive Blundstone Original Series Chelsea Boot

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

New Markdown

Camper Norman Ankle Boot (Men)

$147 – $205Current Price $147 to $205

$205Previous Price $205

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UGG® Heritage Utility Mini Boot (Men)

$149.99Current Price $149.99

$229.95Previous Price $229.95

Ariat Sport Rambler Western Boot (Men)

$179.95Current Price $179.95

New Markdown

Camper Mil 1913 Boot (Men)

$168Current Price $168

$205Previous Price $205

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Camper Pix Chelsea Boot (Men)

$157.50Current Price $157.50

$225Previous Price $225

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Johnston & Murphy Calder Chelsea Boot (Men)

$179Current Price $179

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

$160Current Price $160

Ariat Hybrid Low Boy Western Chelsea Boot (Men)

$159.95Current Price $159.95

Sperry Mini Lug Chukka Boot (Men)

$150Current Price $150

UGG® Idyllwild Lace-Up Boot (Men)

$189.95Current Price $189.95

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$199.95Current Price $199.95

New Markdown

Camper Beetle Ankle Boot (Men)

$192Current Price $192

$235Previous Price $235

Børn Reed Zip-Up Boot (Men)

$150Current Price $150

Timberland Redwood Falls Waterproof Chukka Boot (Men)

$135Current Price $135

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Sperry Avenue Waterproof Duck Boot (Men)

$60Current Price $60

$120Previous Price $120

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Timberland White Ledge Waterproof Hiking Boot (Men)

$120Current Price $120