Men's Boots Comfort Shoes

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Red Wing Weekend Chukka Boot

$269.99Current Price $269.99

4.1(16)

UGG® Men's Neumel Chukka Boot

$154.95Current Price $154.95

4.8(530)

Timberland Britton Road Mid Chelsea Boot

$160Current Price $160

4.6(43)

Cole Haan Roundhill Grand Waterproof Chukka Boot

$260Current Price $260

4.3(10)

Johnston & Murphy Barret Zip Boot

$198.95Current Price $198.95

4.9(20)

Josef Seibel Erroll Waterproof Chukka

$185Current Price $185

Red Wing 1907 Classic Moc Boot

$349.99Current Price $349.99

4.6(577)

Florsheim Anthem Plain Toe Chukka

$145Current Price $145

5(1)

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HOKA Arahi 8 Stability Running Shoe

$120 – $150Current Price $120 to $150

$150Previous Price $150

5(6)

Børn 'Harrison' Chukka Boot

$145Current Price $145

4.1(12)

Aquatalia Bernardo Water Repellent Combat Boot

$495Current Price $495

Børn Harrison Plain Toe Chukka Boot

$145Current Price $145

New

Clarks® Originals Wallabee Leather Shoe

$140 – $180Current Price $140 to $180

Ariat Sport Outdoor Square Toe Cowboy Boot

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

4.8(160)

Vionic Livermore Water Repellent Lace-Up Bootie

$230Current Price $230

4.4(18)

New

Johnston & Murphy Ripley Inside-Zip Boot

$199Current Price $199

Blundstone Footwear Classic Chelsea Boot

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

4.5(24)

Clarks® Originals Clarks® Desert Chukka Boot

$140Current Price $140

4.3(14)

Red Wing Classic Muleskinner Moc Toe Boot

$319.99Current Price $319.99

5(4)

Ariat Wexford Waterproof Chelsea Boot

$199.95Current Price $199.95

4.5(310)

Blundstone Footwear Water Resistant Chelsea Boot

$219.95Current Price $219.95

4.9(33)

Red Wing Iron Ranger Cap Toe Boot

$349.99Current Price $349.99

4.7(801)

New

Johnston & Murphy Clint Chukka Boot

$189Current Price $189

Clarks® Originals Wallabee Chukka Boot

$150Current Price $150

4.6(5)

Mephisto Alexander Chukka Boot

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Ariat Spitfire Chukka Boot

$129.95Current Price $129.95

4.8(365)

ECCO Metropole Prague Chukka Boot

$240Current Price $240

5(1)

New

Johnston & Murphy XCFlex® Daylen Cap Toe Boot

$199Current Price $199

5(1)

New

Johnston & Murphy XC Durham Waterproof Chelsea Boot

$229Current Price $229

4.9(8)

New

Aquatalia Rovello Water Repellent Boot

$425Current Price $425

Ariat Booker Ultra Chelsea Boot

$149.95Current Price $149.95

4.8(848)

PIKOLINOS York Ankle Boot

$220Current Price $220

New

UGG® Birch Hiker Shoe

$194.95Current Price $194.95

Florsheim Forge Lace-Up Boot

$135Current Price $135

UGG® Men's Classic Boot

$194.95Current Price $194.95

4.7(211)

Børn 'Harrison' Chukka Boot

$145Current Price $145

4.1(12)

Blundstone Footwear Thermal Waterproof Genuine Shearling Lined Chelsea Boot

$249.95Current Price $249.95

New

UGG® Neumel Chelsea Boot

$154.95Current Price $154.95

4.7(61)

UGG® Men's Ultra Mini Classic Water Resistant Boot

$164.95Current Price $164.95

4.5(46)

New

Aquatalia Palmiro Water Repellent Boot

$495Current Price $495

Timberland Mt. Maddsen Waterproof Hiking Boot

$125 – $130Current Price $125 to $130

4.6(609)

Blundstone Footwear Water Resistant Chelsea Boot

$199.95Current Price $199.95

Timberland Redwood Edge Essential Water Repellent Boot

$160Current Price $160

4.7(35)

New

Clarks® Cleyhill Top Leather Bootie

$140Current Price $140

Gentle Souls Almada Lug Sole Boot

$250Current Price $250

5(1)

Camper Peu Path Ankle Boot

$215Current Price $215

Gentle Souls Santo Chelsea Boot

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

$250Previous Price $250

4.5(2)

Ariat Sport Wide Square Toe Cowboy Boot

$189.95Current Price $189.95

4.8(461)

New

Florsheim Redford Leather Wingtip Lace Up Boot

$145Current Price $145

UGG® Men's Classic Mini Boot

$174.95Current Price $174.95

4.8(37)

Blundstone Footwear Original Water Resistant Chelsea Boot

$209.95Current Price $209.95

4.7(31)

New

Florsheim Rucci Lug Plain Toe Chelsea Boot

$155Current Price $155

New

Rockport Oakes Leather Chukka Boot

$160Current Price $160

Josef Seibel Earl 04 Chukka Boot

$180Current Price $180

5(1)

Clarks® Cleyhill Hi Boot

$130Current Price $130

New

Johnston & Murphy Britton Plain Toe Boot

$199Current Price $199

Camper Peu Terreno Leather Moccasin

$215Current Price $215

Ariat Booker Ultra Square Toe Western Chelsea Boot

$149.95Current Price $149.95

4.8(849)

New

UGG® Classic Ultra Mini Weather Hybrid Boot

$204.95Current Price $204.95

5(1)

Clarks® Wallabee Suede Boot

$110Current Price $110

5(8)

Gentle Souls Chaves Suede Chukka Boot

$225Current Price $225

Johnston & Murphy Calder Plain Toe Chelsea Boot

$188.95Current Price $188.95

3.8(20)

Cole Haan Grand Neoclassic Flexcraft Chukka Boot

$220Current Price $220

Florsheim Rucci Plain Toe Chukka Boot

$155Current Price $155

Camper Dean Chelsea Boot

$245Current Price $245

5(2)

New

Johnston & Murphy Clint Chelsea Boot

$189Current Price $189

PIKOLINOS Vigo Water Resistant Boot

$230Current Price $230

New

Ariat Spitfire Chukka Boot

$139.95Current Price $139.95

4.8(364)

Johnston & Murphy Barrett Plain Toe Boot

$149Current Price $149

$199Previous Price $199

3.9(9)

Camper Brutus Chelsea Boot

$250Current Price $250

Clarks® Originals 'Desert' Boot

$140Current Price $140

4.6(138)