Men's Cushioned Insoles Boots

Johnston & Murphy Upton Chukka (Men)

$119.99Current Price $119.99

$179Previous Price $179

Blundstone Footwear Classic Chelsea Boot (Men)

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

Vince Jerome Suede Lugged Chukka Boot (Men) (Nordstrom Exclusive)

$298Current Price $298

ECCO Metropole London Waterproof Suede Chukka Boot (Men)

$159.99 – $172.50Current Price $159.99 to $172.50

$229.95Previous Price $229.95

TO BOOT NEW YORK Christophe Chelsea Boot (Men)

$495Current Price $495

Rockport Cassius Chelsea Boot (Men)

$160Current Price $160

Gordon Rush Austin Chukka Boot (Men)

$290Current Price $290

Blundstone Footwear Heritage Chelsea Boot (Men)

$354.95Current Price $354.95

BOSS Dresletic Suede Chukka Boot (Men) (Exclusive Retailer)

$399Current Price $399

Magnanni Borazo Lug Sole Boot (Men)

$499Current Price $499

Bruno Magli Vestri Ankle Boot (Men)

$425Current Price $425

ECCO Track 25 Waterproof Boot (Men)

$274.95Current Price $274.95

Florsheim Forge Chukka Boot (Men)

$130Current Price $130

Johnston & Murphy Calder 175th Chukka Boot (Men)

$175Current Price $175

Johnston & Murphy XC Flex Connelly Lace-Up Leather Boot (Men)

$149.99Current Price $149.99

$199Previous Price $199

Florsheim Traveler Chukka Boot (Men)

$135Current Price $135

Vionic Uptown Jackson Boot - Wide Width Available (Men)

$230Current Price $230

Josef Seibel Erroll Waterproof Chukka (Men)

$185Current Price $185

Pajar Fero 2.0 Waterproof Ankle Boot (Men)

$195Current Price $195

Rockport Flynn Plain Toe Derby Boot (Men)

$160Current Price $160

Magnanni Grayson Lace-Up Lug Sole Boot (Men)

$525Current Price $525

Blundstone Footwear Water Resistant Classics Chelsea Boot (Men)

$209.95Current Price $209.95

Vionic Livermore Water Repellent Lace-Up Bootie (Men)

$230Current Price $230

Blundstone Footwear Water Resistant Chelsea Boot (Men)

$209.95Current Price $209.95

Alden Barrie Chukka Boot (Men)

$682Current Price $682

New!

SOREL Cyprus™ Waterproof Boot (Men)

$135Current Price $135

Johnston & Murphy Calder 175th Chelsea Boot (Men)

$175Current Price $175

New!

Kenneth Cole New York Wilhem Chukka Boot (Men)

$165Current Price $165

Barbour Ridge Wellington Rain Boot (Men)

$135 – $150Current Price $135 to $150

New Markdown

Dune London Smoky Plain Toe Chukka Boot (Men)

$117Current Price $117

$195Previous Price $195

ECCO Offroad Waterproof Hiking Boot (Men)

$120.21Current Price $120.21

$184.95Previous Price $184.95

Warfield & Grand Roseberg Derby Boot (Men)

$199Current Price $199

Wolverine 1000 Mile Legacy Pavedway Boot (Men)

$189.95Current Price $189.95

Florsheim Forge Chelsea Boot (Men)

$130Current Price $130

Magnanni Maurilio Chukka Boot (Men)

$550Current Price $550

Gordon Rush Matthews Chelsea Boot (Men)

$176.90Current Price $176.90

$265Previous Price $265

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New!

Merrell Moab 3 Mid Hiking Shoe (Men)

$150Current Price $150

UGG® Classic Mini Boot (Men)

$169.95Current Price $169.95

KLEMAN Oxal KP Lugged Leather Boot (Men)

$295Current Price $295

Wolverine 1000 Mile Legacy Plain Toe Boot (Men)

$159.95Current Price $159.95

Kenneth Cole New York Raymond Chelsea Boot (Men)

$185Current Price $185

Kenneth Cole Reaction Hulard Chelsea Boot (Men)

$129Current Price $129

New Markdown

Johnston & Murphy XC Flex Connelly Wingtip Boot (Men)

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

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

OluKai Mōlina Water Repellent Boot (Men)

$150Current Price $150

Børn Nigel Low Boot (Men)

$150Current Price $150

Eastland Allagash Standard Derby Boot (Men)

$145Current Price $145

Florsheim Forge Lace-Up Boot (Men)

$135Current Price $135

Mephisto Alexander Chukka Boot (Men)

$399Current Price $399

TO BOOT NEW YORK Hansen Boot (Men)

$625Current Price $625

Florsheim Launch Plain Toe Chukka (Men)

$135Current Price $135

New!

Zelli Italia Campo Chukka Boot (Men)

$695Current Price $695

New!

SOREL Cyprus™ Waterproof Chelsea Boot (Men)

$125Current Price $125

Robert Barakett Murphey Chelsea Boot (Men)

$348Current Price $348

New Markdown

Birkenstock Highwood Chelsea Boot (Men)

$124.99 – $137.50Current Price $124.99 to $137.50

$209.95Previous Price $209.95

New!

Kenneth Cole New York Tully Chelsea Boot (Men)

$185Current Price $185

SOREL Slabtown 62™ Stoic Chukka Boot (Men)

$160Current Price $160

Frye Paul Leather Boot (Men)

$228Current Price $228

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SOREL Slabtown 62 Waterproof Chelsea Boot (Men)

$170Current Price $170

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

$239.95Current Price $239.95

A. Veer Robert Lace-up Boot

$149Current Price $149

Warfield & Grand MMXXIV Cap Toe Boot (Men)

$199Current Price $199

Ariat Sport Rodeo Cowboy Boot (Men)

$189.95Current Price $189.95

Stacy Adams Townsend Chelsea Boot (Men)

$150Current Price $150

Blake Mckay Alder Chukka Boot (Men)

$99.90Current Price $99.90

$165Previous Price $165

Blundstone Footwear Classic 550 Series Water Resistant Chelsea Boot (Men)

$199.95Current Price $199.95

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Stacy Adams Eastmont Boot (Men)

$140Current Price $140

Ariat Sport Big Country Wide Square Toe Cowboy Boot (Men)

$189.95Current Price $189.95

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

$274.95Current Price $274.95

Allen Edmonds Dain Combat Boot (Men)

$272.25Current Price $272.25

$495Previous Price $495

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Kenneth Cole Reaction Vesto Chukka Boot (Men)

$119Current Price $119

Blundstone Footwear Original Water Resistant Chelsea Boot (Men)

$184.95Current Price $184.95