Men's Comfort Boots

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Florsheim Anthem Plain Toe Chukka

$145Current Price $145

5(1)

Cole Haan Roundhill Grand Waterproof Chukka Boot

$260Current Price $260

4.3(10)

Florsheim Anthem Plain Toe Chelsea Boot

$145Current Price $145

3.8(4)

New

Ariat Rambler Recon Square Toe Chelsea Boot

$159.95 – $169.95Current Price $159.95 to $169.95

5(8)

Rockport Cassius Chelsea Boot

$160Current Price $160

4.3(6)

New

Timberland Redwood Edge Essential Water Repellent Chelsea Boot

$140Current Price $140

4.7(25)

Johnston & Murphy Jameson Chelsea Boot

$199Current Price $199

$295Previous Price $295

5(1)

Johnston & Murphy Latham Cap Toe Combat Boot

$328Current Price $328

4.8(6)

Florsheim Launch Plain Toe Chukka

$135Current Price $135

Johnston & Murphy Barrett Plain Toe Boot

$149Current Price $149

$199Previous Price $199

3.9(9)

Ariat Hybrid Low Boy Western Chelsea Boot

$159.95Current Price $159.95

4.8(197)

Johnston & Murphy Barret Zip Boot

$198.95Current Price $198.95

4.9(20)

Ariat Wexford Waterproof Chelsea Boot

$199.95Current Price $199.95

4.5(305)

Gentle Souls Santo Chelsea Boot

$149.99 – $250Current Price $149.99 to $250

$250Previous Price $250

5(1)

New

Clarks® Cleyhill Top Leather Bootie

$140Current Price $140

New

Camper Brutus Chelsea Boot

$250Current Price $250

Florsheim Forge Chukka Boot

$130Current Price $130

5(2)

Ariat Sport Wide Square Toe Cowboy Boot

$189.95Current Price $189.95

4.8(453)

Ariat Sport Outdoor Square Toe Cowboy Boot

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

4.8(151)

Red Wing Weekend Chukka Boot

$269.99Current Price $269.99

3.9(14)

Johnston & Murphy Durham Waterproof Cap Toe Boot

$228.95 – $238.95Current Price $228.95 to $238.95

4.9(7)

ECCO Metropole Prague Chukka Boot

$240Current Price $240

Florsheim Forge Lace-Up Boot

$135Current Price $135

Johnston & Murphy Calder Chelsea Boot

$188.95Current Price $188.95

4(4)

PIKOLINOS York M2M Lace-Up Cap Toe Boot

$250Current Price $250

4.5(2)

UGG® Neumel Chelsea Boot

$154.95Current Price $154.95

4.7(61)

Clarks® Originals Clarks® Desert Chukka Boot

$140Current Price $140

4.3(12)

Florsheim Traveler Chukka Boot

$135Current Price $135

3(1)

Vionic Uptown Jackson Boot - Wide Width Available

$230Current Price $230

5(3)

New

Cole Haan Grand Neoclassic Flexcraft Chukka Boot

$220Current Price $220

Only a few left

New

Mephisto Alexander Chukka Boot

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Johnston & Murphy Calder Oiled Suede Chukka Boot

$188.95Current Price $188.95

4.6(10)

Johnston & Murphy Reeve Zip Boot

$139.85Current Price $139.85

5(2)

New

Clarks® Cleyhill Hi Boot

$130Current Price $130

New

Camper Peu Terreno Chukka

$225Current Price $225

Ariat Booker Ultra Square Toe Western Chelsea Boot

$149.95Current Price $149.95

4.8(838)

Camper Peu Path Ankle Boot

$215Current Price $215

Ariat Heritage R Toe Western Boot

$199.95Current Price $199.95

4.7(464)

Aquatalia Prospero Water Resistant Chelsea Boot

$450Current Price $450

Red Wing Iron Ranger Cap Toe Boot

$349.99Current Price $349.99

4.7(800)

Børn Nigel Low Boot

$150Current Price $150

4.1(7)

Aquatalia Denali Water Resistant Lace-Up Boot

$550Current Price $550

5(1)

Josef Seibel Erroll Waterproof Chukka

$185Current Price $185

New

Aquatalia Danny Water Resistant Lace-Up Boot

$550Current Price $550

Aquatalia Bernardo Water Repellent Combat Boot

$495Current Price $495

Mephisto Berto Chukka Boot

$439Current Price $439

5(3)

Florsheim Lodge Plain Toe Boot

$145Current Price $145

PIKOLINOS Vigo Water Resistant Boot

$230Current Price $230

New

Camper Brutus Leather Ankle Boot

$235Current Price $235

Florsheim Forge Chelsea Boot

$130Current Price $130

5(2)

New

KEEN Targhee Apex Mid Waterproof Hiking Boot

$185 – $190Current Price $185 to $190

5(4)

Birkenstock Uppsala Mid Boot

$169.95Current Price $169.95

3(2)

Ariat Sport Rambler Western Boot

$179.95Current Price $179.95

4.8(82)

Timberland Britton Road Mid Chelsea Boot

$160Current Price $160

4.6(41)

Camper Pelotas Ariel Boot

$300Current Price $300

4(1)

Johnston & Murphy Calder Plain Toe Chelsea Boot

$188.95Current Price $188.95

3.9(19)

Timberland Redwood Edge Essential Water Repellent Boot

$160Current Price $160

4.8(27)

Ariat Maverick Western Boot

$259.95Current Price $259.95

4.7(14)

Ariat Booker Ultra Chelsea Boot

$149.95Current Price $149.95

4.8(841)

Rockport Flynn Plain Toe Derby Boot

$160Current Price $160

3.8(4)

UGG® Truckee Field Boot

$154.95Current Price $154.95

5(6)

Ariat Wexford Waterproof Chelsea Boot

$209.95Current Price $209.95

4.6(286)

New

Ariat Spitfire Chukka Boot

$129.95Current Price $129.95

4.7(344)

Ariat Booker Ultra Chelsea Boot

$149.95Current Price $149.95

4.8(836)

Camper Peu Terreno Short Boot

$300Current Price $300

5(2)

Only a few left

Blundstone Footwear Blundstone Chelsea Boot

$219.95Current Price $219.95

4.7(156)

Aquatalia Fortino Water Repellent Boot

$625Current Price $625

4(1)

Only a few left

Blundstone Footwear Classic Chelsea Boot

$219.95 – $229.95Current Price $219.95 to $229.95

4.5(24)

Camper Peu Serra Ankle Boot

$230 – $235Current Price $230 to $235

4(1)

Timberland White Ledge Waterproof Hiking Boot

$130Current Price $130

4.6(512)

Vionic Livermore Water Repellent Lace-Up Bootie

$230Current Price $230

4.4(17)