Men's Boots Comfort Shoes

Free Delivery by Christmas

Cole Haan Roundhill Grand Waterproof Chukka Boot (Men)

$260Current Price $260

Free Delivery by Christmas

UGG® Neumel Chukka Boot (Men)

$149.95Current Price $149.95

Free Delivery by Christmas

Ariat Hilo Moc Toe Slip-On (Men)

$89.95Current Price $89.95

Free Delivery by Christmas

Blundstone Footwear Classic Chelsea Boot (Men)

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

Free Delivery by Christmas

Johnston & Murphy Upton Chukka (Men)

$119.99Current Price $119.99

$179Previous Price $179

Free Delivery by Christmas

Blundstone Footwear Classic 587 Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

Free Delivery by Christmas

UGG® Neumel Era Chukka Boot (Men)

$119.96Current Price $119.96

$159.95Previous Price $159.95

Free Delivery by Christmas

Josef Seibel Erroll Waterproof Chukka (Men)

$185Current Price $185

Free Delivery by Christmas

Johnston & Murphy Calder Chukka Boot (Men)

$179Current Price $179

Free Delivery by Christmas

Blundstone Footwear Water Resistant Lace-Up Boot (Men)

$234.95Current Price $234.95

Free Delivery by Christmas

Johnston & Murphy Upton Chelsea Boot (Men)

$119.99Current Price $119.99

$179Previous Price $179

Free Delivery by Christmas

Timberland 6-Inch Premium Waterproof Boot (Men)

$199Current Price $199

Free Delivery by Christmas

Johnston & Murphy Barret Zip Boot (Men)

$199Current Price $199

Free Delivery by Christmas

Blundstone Footwear Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

Free Delivery by Christmas

Timberland Redwood Falls Waterproof Lace-Up Boot (Men)

$160Current Price $160

Free Delivery by Christmas

Johnston & Murphy Braxton Chukka Boot (Men)

$159Current Price $159

Free Delivery by Christmas

Blundstone Footwear Blundstone City Chelsea Boot (Men)

$224.95 – $234.95Current Price $224.95 to $234.95

Free Delivery by Christmas

Clarks® Originals Clarks® Desert Chukka Boot (Men)

$150Current Price $150

Free Delivery by Christmas

Ariat Wexford Waterproof Chelsea Boot (Men)

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

Free Delivery by Christmas

Johnston & Murphy Barrett Plain Toe Boot (Men)

$199Current Price $199

Free Delivery by Christmas

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

$274.95Current Price $274.95

Free Delivery by Christmas

Cole Haan Muir Waterproof Moc Toe Boot (Men)

$208Current Price $208

Free Delivery by Christmas

UGG® Ultra Mini Classic Water Resistant Boot (Men)

$159.95Current Price $159.95

Free Delivery by Christmas

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$184.95Current Price $184.95

Free Delivery by Christmas

Nordstrom Italian Collection Saluzzo Chukka Boot (Men)

$229.95Current Price $229.95

Free Delivery by Christmas

Clarks® Originals Wallabee Chukka Boot (Men)

$160 – $170Current Price $160 to $170

Free Delivery by Christmas

UGG® Neumel Chelsea Boot (Men)

$149.95Current Price $149.95

Free Delivery by Christmas

UGG® Classic Mini Boot (Men)

$169.95Current Price $169.95

Free Delivery by Christmas

Johnston & Murphy Calder Oiled Suede Chukka Boot (Men)

$179Current Price $179

Free Delivery by Christmas

Rockport Cassius Chelsea Boot (Men)

$160Current Price $160

Free Delivery by Christmas

Johnston & Murphy Parker Waterproof Chukka Boot (Men)

$129.99Current Price $129.99

$189Previous Price $189

Free Delivery by Christmas

Børn Reed Zip-Up Boot (Men)

$150Current Price $150

Free Delivery by Christmas

PIKOLINOS Vigo Water Resistant Boot (Men)

$215Current Price $215

Free Delivery by Christmas

Blundstone Footwear Classic Chelsea Boot (Men)

$219.95Current Price $219.95

Free Delivery by Christmas

Blundstone Footwear Plain Toe Chelsea Boot (Men)

$209.95Current Price $209.95

Free Delivery by Christmas

Børn Nigel Low Boot (Men)

$150Current Price $150

Free Delivery by Christmas

Sperry Mini Lug Chukka Boot (Men)

$150Current Price $150

Free Delivery by Christmas

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

$274.95Current Price $274.95

Free Delivery by Christmas

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

$140 – $150Current Price $140 to $150

Free Delivery by Christmas

Blundstone Footwear Gender Inclusive Blundstone Original Series Chelsea Boot

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

Free Delivery by Christmas

Mephisto Leonardo HydroProtect Waterproof Genuine Shearling Lined Boot (Men)

$469Current Price $469

Free Delivery by Christmas

Ariat Sport Rambler Western Boot (Men)

$179.95Current Price $179.95

Free Delivery by Christmas

Børn Nigel Low Boot (Men)

$150Current Price $150

Free Delivery by Christmas

Clarks® Originals Desert Boot (Men)

$160Current Price $160

Free Delivery by Christmas

Blundstone Footwear Gender Inclusive Chelsea Boot

$209.95Current Price $209.95

Free Delivery by Christmas

Josef Seibel Earl 04 Chukka Boot (Men)

$180Current Price $180

Free Delivery by Christmas

Timberland Premium Waterproof Lace-Up Chukka Boot (Men)

$150Current Price $150

Free Delivery by Christmas

Mephisto Berto Chukka Boot (Men)

$439Current Price $439

Free Delivery by Christmas

Johnston & Murphy Calder Plain Toe Chelsea Boot (Men)

$179Current Price $179

Free Delivery by Christmas

Ariat Slingshot Square Toe Cowboy Boot (Men)

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

Free Delivery by Christmas

Ariat Circuit Patriot Cowboy Boot (Men)

$209.95Current Price $209.95

Free Delivery by Christmas

Johnston & Murphy Durham Waterproof Cap Toe Boot (Men)

$199 – $229Current Price $199 to $229

Free Delivery by Christmas

Ariat Hybrid Low Boy Western Chelsea Boot (Men)

$159.95Current Price $159.95

Free Delivery by Christmas

Clarks® Originals Wallabee RB Chukka (Men)

$160Current Price $160

Free Delivery by Christmas

Red Wing 1907 Classic Moc Boot (Men)

$349.99Current Price $349.99

Free Delivery by Christmas

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$199.95Current Price $199.95

Free Delivery by Christmas

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$184.95Current Price $184.95

Free Delivery by Christmas

Aquatalia Golliard Water Resistant Chukka Boot (Men)

$495Current Price $495

Free Delivery by Christmas

Vionic Danfield Desert Boot (Men)

$210Current Price $210

Free Delivery by Christmas

Blundstone Footwear Heritage Chelsea Boot (Men)

$354.95Current Price $354.95

Free Delivery by Christmas

Ariat Midtown Rambler Mid Chelsea Boot (Men)

$169.95Current Price $169.95

Free Delivery by Christmas

Vionic Uptown Jackson Boot - Wide Width Available (Men)

$230Current Price $230

Free Delivery by Christmas

Florsheim Forge Chukka Boot (Men)

$130Current Price $130

Free Delivery by Christmas

Johnston & Murphy Upton Chukka (Men)

$179Current Price $179

Free Delivery by Christmas

OluKai Mōlina Water Repellent Boot (Men)

$150Current Price $150

Free Delivery by Christmas

Sperry Clifton Chelsea Waterproof Duck Boot (Men)

$115Current Price $115

Free Delivery by Christmas

Pajar Fero 2.0 Waterproof Ankle Boot (Men)

$195Current Price $195

Free Delivery by Christmas

Camper Norman Ankle Boot (Men)

$147 – $205Current Price $147 to $205

$205Previous Price $205

Free Delivery by Christmas

Ariat Booker Ultra Chelsea Boot (Men)

$149.95Current Price $149.95

Free Delivery by Christmas

Aquatalia Bernardo Water Repellent Combat Boot (Men)

$495Current Price $495

Free Delivery by Christmas

Blundstone Footwear Water Resistant Classics Chelsea Boot (Men)

$209.95Current Price $209.95