Men's Boots Comfort Shoes

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Florsheim Launch Plain Toe Chukka

$135Current Price $135

Blundstone Footwear Water Resistant Lace-Up Boot

$244.95Current Price $244.95

Ariat Booker Ultra Chelsea Boot

$149.95Current Price $149.95

4.8(838)

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HOKA Arahi 8 Stability Running Shoe

$150Current Price $150

5(6)

Red Wing Weekend Chukka Boot

$269.99Current Price $269.99

3.9(14)

PIKOLINOS York Ankle Boot

$220Current Price $220

New

Aquatalia Danny Water Resistant Lace-Up Boot

$550Current Price $550

Ariat Wexford Waterproof Chelsea Boot

$199.95Current Price $199.95

4.5(304)

Rockport Cassius Chelsea Boot

$160Current Price $160

4.3(6)

Merrell Moab 3 Mid Waterproof Hiking Shoe

$155Current Price $155

4.4(174)

New

Camper Brutus Chelsea Boot

$250Current Price $250

Aquatalia Denali Water Resistant Lace-Up Boot

$550Current Price $550

5(1)

Vionic Uptown Jackson Boot - Wide Width Available

$230Current Price $230

5(2)

Johnston & Murphy Durham Waterproof Cap Toe Boot

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

4.9(7)

New

Cole Haan Grand Neoclassic Flexcraft Chukka Boot

$220Current Price $220

Ariat Hybrid Low Boy Western Chelsea Boot

$159.95Current Price $159.95

4.8(197)

Aquatalia Prospero Water Resistant Chelsea Boot

$450Current Price $450

New

Camper Peu Terreno Chukka

$225Current Price $225

Clarks® Originals Clarks® Desert Trek Chukka Boot

$140 – $150Current Price $140 to $150

5(4)

Josef Seibel Erroll Waterproof Chukka

$185Current Price $185

Camper Pix Leather Ankle Boot

$215Current Price $215

Florsheim Anthem Plain Toe Chukka

$145Current Price $145

Johnston & Murphy Barret Zip Boot

$198.95Current Price $198.95

4.9(20)

Florsheim Forge Lace-Up Boot

$135Current Price $135

New

Timberland Gridworks 6" Waterproof Work Boot

$170 – $180Current Price $170 to $180

4.4(60)

Ariat Booker Ultra Square Toe Western Chelsea Boot

$149.95Current Price $149.95

4.8(835)

New

Ariat Spitfire Chukka Boot

$129.95Current Price $129.95

4.7(344)

Red Wing Iron Ranger Cap Toe Boot

$349.99Current Price $349.99

4.7(800)

Merrell Thermo Chill 2 Waterproof Boot

$150Current Price $150

4.5(26)

New

UGG® Birch Hiker Shoe

$194.95Current Price $194.95

Timberland TiTAN EV 6" Waterproof Composite Toe Work Boot

$165 – $175Current Price $165 to $175

4.2(158)

Mephisto Berto Chukka Boot

$439Current Price $439

5(3)

Blundstone Footwear All Terrain Series Water Resistant Chelsea Boot

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

5(2)

Clarks® Originals Clarks® Desert Chukka Boot

$140Current Price $140

4.3(12)

Aquatalia Bernardo Water Repellent Combat Boot

$495Current Price $495

Ariat Sport Cool VentTEK™ Cowboy Boot

$199.95Current Price $199.95

4.6(72)

Ariat Spitfire H2O Waterproof Chukka Boot

$139.95Current Price $139.95

4.5(60)

Timberland Britton Road Mid Chelsea Boot

$150 – $160Current Price $150 to $160

4.6(41)

ECCO Track 25 Waterproof Boot

$275Current Price $275

4.6(38)

Blundstone Footwear Gender Inclusive Blundstone Original Series Chelsea Boot

$179.95 – $194.95Current Price $179.95 to $194.95

4.3(6)

Gentle Souls Santo Chelsea Boot

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

$250Previous Price $250

5(1)

Blundstone Footwear Original Water Resistant Chelsea Boot

$209.95Current Price $209.95

4.8(30)

Ariat Clean Country Shoe

$139.95Current Price $139.95

4.5(27)

Timberland Redwood Edge Essential Water Repellent Boot

$160Current Price $160

4.8(27)

Blundstone Footwear All Terrain Chelsea Service Shoe

$239.95Current Price $239.95

5(2)

Vionic Livermore Water Repellent Lace-Up Bootie

$230Current Price $230

4.4(17)

New

Mephisto Alexander Chukka Boot

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New

Camper Brutus Leather Ankle Boot

$235Current Price $235

Camper Peu Path Ankle Boot

$215Current Price $215

UGG® Neumel Chelsea Boot

$112.50 – $154.95Current Price $112.50 to $154.95

$154.95Previous Price $154.95

4.7(61)

Mephisto Pitt Mid Lace-Up Boot

$499Current Price $499

4.4(17)

Josef Seibel Earl 04 Chukka Boot

$180Current Price $180

5(1)

Ariat Rambler Recon Square Toe Chelsea Boot

$159.95Current Price $159.95

5(8)

Ariat Sport Rambler Western Boot

$179.95Current Price $179.95

4.8(82)

UGG® Neumel Chukka Boot

$154.95Current Price $154.95

4.8(530)

UGG® Classic Mini Boot

$174.95Current Price $174.95

4.8(37)

UGG® Truckee Field Boot

$154.95Current Price $154.95

5(6)

New

Ariat Hybrid Rancher Cowboy Boot

$199.95Current Price $199.95

4.6(284)

Florsheim Anthem Plain Toe Chelsea Boot

$145Current Price $145

3.8(4)

Ariat Point Ryder Western Boot

$249.95Current Price $249.95

4.2(97)

Ariat Sport Wide Square Toe Cowboy Boot

$189.95Current Price $189.95

4.8(452)

Gentle Souls Chaves Suede Chukka Boot

$225Current Price $225

Aquatalia Prospero Chelsea Boot

$450Current Price $450

Johnston & Murphy Reeve Zip Boot

$139.85Current Price $139.85

5(2)

Blundstone Footwear Original Water Resistant Chelsea Boot

$194.95Current Price $194.95

1(1)

Ariat Booker Wide Square Toe Western Chelsea Boot

$149.95Current Price $149.95

4.8(832)

UGG® Adirondack XXV Boot

$249.95Current Price $249.95

3.6(7)

New

Camper Pix Berlin Leather Ankle Boot

$285Current Price $285

Ariat Booker Ultra Square Toe Western Chelsea Boot

$149.95Current Price $149.95

4.8(108)

Timberland Premium 6-Inch Waterproof Boot

$220Current Price $220

4.6(2775)

Johnston & Murphy Hartford Chelsea Boot

$328Current Price $328

5(5)