Men's Comfort Boots

Cole Haan Roundhill Grand Waterproof Chukka Boot (Men)

$260Current Price $260

4.5(19)

Clarks® Originals Clarks® Desert Chukka Boot (Men)

$140 – $150Current Price $140 to $150

4.3(11)

Red Wing Weekend Chukka Boot (Men)

$269.99Current Price $269.99

4.3(10)

Blundstone Footwear Classic Chelsea Boot (Men)

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

4.9(21)

New

Rockport Flynn Plain Toe Derby Boot (Men)

$160Current Price $160

3.8(4)

Ariat Hybrid Low Boy Western Chelsea Boot (Men)

$159.95Current Price $159.95

4.7(166)

Florsheim Anthem Plain Toe Chelsea Boot (Men)

$145Current Price $145

4.5(2)

Gentle Souls Almada Lug Sole Boot (Men)

$250Current Price $250

Timberland Oak Forge Boot (Men)

$225Current Price $225

5(5)

Ariat Booker Ultra Chelsea Boot (Men)

$149.95Current Price $149.95

4.8(767)

Johnston & Murphy XC Flex Connelly Wingtip Boot (Men)

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

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

4.2(59)

Ariat Hilo Moc Toe Slip-On (Men)

$89.95Current Price $89.95

4.9(117)

Johnston & Murphy Calder Oiled Suede Chukka Boot (Men)

$179Current Price $179

4.6(10)

Florsheim Traveler Chukka Boot (Men)

$135Current Price $135

3(1)

Blundstone Footwear Classic 587 Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

4.9(23)

Gentle Souls Santo Chelsea Boot (Men)

$250Current Price $250

Blundstone Footwear Gender Inclusive Blundstone Original Series Chelsea Boot

$179.95 – $189.95Current Price $179.95 to $189.95

4.3(6)

Gentle Souls Torres Chukka Boot (Men)

$250Current Price $250

Florsheim Forge Chelsea Boot (Men)

$130Current Price $130

5(2)

Blundstone Footwear Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

4.9(32)

Mephisto Berto Chukka Boot (Men)

$439Current Price $439

5(3)

Vionic Livermore Water Repellent Lace-Up Bootie (Men)

$230Current Price $230

4.3(16)

Florsheim Launch Plain Toe Chukka (Men)

$135Current Price $135

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$199.95Current Price $199.95

4.8(29)

Only a few left

Ariat Booker Ultra Chelsea Boot (Men)

$149.95Current Price $149.95

4.8(772)

Timberland Redwood Falls Waterproof Lace-Up Boot (Men)

$160Current Price $160

4.6(140)

Merrell Moab 3 Mid Waterproof Hiking Shoe (Men)

$169.99 – $175Current Price $169.99 to $175

4.4(505)

Florsheim Anthem Plain Toe Chukka (Men)

$145Current Price $145

Johnston & Murphy Durham Waterproof Cap Toe Boot (Men)

$219Current Price $219

4.9(7)

Johnston & Murphy Calder Chukka Boot (Men)

$179Current Price $179

4.2(35)

Nordstrom For Good

UGG® Idyllwild Lace-Up Boot (Men)

$189.95Current Price $189.95

5(1)

Florsheim Forge Lace-Up Boot (Men)

$135Current Price $135

Florsheim Forge Chukka Boot (Men)

$130Current Price $130

5(2)

Bogs Kicker II Waterproof Chelsea Rain Boot (Men)

$95Current Price $95

4.5(37)

Timberland Premium 6-Inch Waterproof Boot (Men)

$199Current Price $199

4.6(2755)

Florsheim Rucci Plain Toe Chukka Boot

$155Current Price $155

New

Ariat Wexford Waterproof Chelsea Boot (Men)

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

4.6(288)

KEEN Pyrenees Hiking Boot (Men)

$125.99Current Price $125.99

$180Previous Price $180

4.2(332)

Hoss Boot Company HOSS Chiller Composite Toe Insulated Waterproof Work Boot

$150Current Price $150

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

$140 – $150Current Price $140 to $150

5(4)

Rockport Cassius Chelsea Boot (Men)

$160Current Price $160

4.3(6)

Ariat 'Heritage' Boot

$199.95Current Price $199.95

4.7(401)

Blundstone Footwear Water Resistant Classics Chelsea Boot (Men)

$224.95Current Price $224.95

Ariat Booker Ultra Square Toe Western Chelsea Boot (Men)

$149.95Current Price $149.95

4.8(769)

Blundstone Footwear Original Faux Leather Chelsea Boot (Men)

$126.71 – $146.21Current Price $126.71 to $146.21

$194.95Previous Price $194.95

Blundstone Footwear Blundstone City Chelsea Boot (Men)

$234.95Current Price $234.95

5(3)

Hoss Boot Company HOSS Buster Low Composite Toe Athletic Work Shoe

$130 – $140Current Price $130 to $140

Ariat Sport Wide Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

4.8(431)

Red Wing 6 Inch Moc Toe Boot

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

4.5(652)

Ariat Sport Rambler Western Boot (Men)

$179.95Current Price $179.95

4.8(80)

Ariat Booker Wide Square Toe Western Chelsea Boot (Men)

$149.95Current Price $149.95

4.8(767)

Nordstrom For Good

UGG® Neumel Era Chukka Boot (Men)

$99.99Current Price $99.99

$159.95Previous Price $159.95

4.6(20)

Ariat Heritage R Toe Western Boot (Men)

$199.95Current Price $199.95

4.7(431)

Johnston & Murphy Calder Plain Toe Chelsea Boot (Men)

$179Current Price $179

4.1(18)

Johnston & Murphy Parker Waterproof Chukka Boot (Men)

$129.99Current Price $129.99

$189Previous Price $189

4.8(12)

Red Wing Classic Muleskinner Moc Toe Boot (Men)

$319.99Current Price $319.99

5(3)

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$189.95Current Price $189.95

1(1)

Ariat Sport Herdsman Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

4.8(170)

Johnston & Murphy Calder Chelsea Boot (Men)

$179Current Price $179

5(2)

Blundstone Footwear Plain Toe Chelsea Boot (Men)

$209.95Current Price $209.95

4(4)

Ariat Sport Outdoor Square Toe Cowboy Boot (Men)

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

4.8(130)

Josef Seibel Erroll Waterproof Chukka (Men)

$185Current Price $185

Johnston & Murphy Upton Chelsea Boot (Men)

$169Current Price $169

4.6(134)

Only a few left

New

Timberland Britton Road Mid Chelsea Boot (Men)

$160Current Price $160

4.6(40)

Nordstrom For Good

UGG® Classic Boot (Men)

$189.95Current Price $189.95

4.7(210)

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$189.95Current Price $189.95

Aquatalia Golliard Water Resistant Chukka Boot (Men)

$495Current Price $495

3(2)

Johnston & Murphy Dudley Wingtip Lug Boot (Men)

$328Current Price $328

3.9(11)

Only a few left

Florsheim Lodge Plain Toe Boot (Men)

$145Current Price $145

Bogs Digger Waterproof Ankle Boot (Men)

$85Current Price $85

3.7(54)

Red Wing Iron Ranger Cap Toe Boot (Men)

$349.99Current Price $349.99

4.7(788)