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1071 items
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Cole Haan
Roundhill Grand Waterproof Chukka Boot (Men)
$260
Current Price $260
Frye
Paul Chukka (Men)
$188
Current Price $188
Mephisto
Berto Chukka Boot (Men)
$439
Current Price $439
Blundstone Footwear
Classic Chelsea Boot (Men)
$209.95 – $219.95
Current Price $209.95 to $219.95
SOREL
Madson II Moc Toe Waterproof Boot (Men)
$200
Current Price $200
Johnston & Murphy
Calder Chukka Boot (Men)
$179
Current Price $179
Vince
Jerome Suede Lugged Chukka Boot (Men) (Nordstrom Exclusive)
$298
Current Price $298
Frye
Paul Suede Chukka Boot (Men)
$188 – $198
Current Price $188 to $198
BOSS
Derrk Chelsea Boot (Men)
$299
Current Price $299
TO BOOT NEW YORK
Largo Chelsea Boot (Men)
$495
Current Price $495
SOREL
Madson II Waterproof Chukka Boot (Men)
$190
Current Price $190
FERRAGAMO
Angle Chelsea Boot (Men)
$1,190
Current Price $1,190
Christian Louboutin
Alpinsol Chelsea Boot (Men)
$1,345
Current Price $1,345
Johnston & Murphy
Durham Waterproof Cap Toe Boot (Men)
$199 – $229
Current Price $199 to $229
Rockport
Cassius Chelsea Boot (Men)
$160
Current Price $160
Bruno Magli
Carlo Leather Chukka Boot (Men)
$375
Current Price $375
Cole Haan
Judson Grand Chelsea Boot (Men)
$260
Current Price $260
New!
Aquatalia
Golliard Water Resistant Chukka Boot (Men)
$495
Current Price $495
New!
BOSS
Kope Suede Chukka Boot (Men)
$230
Current Price $230
Tod's
Polacco Gomma Chukka Boot (Men)
$975
Current Price $975
Johnston & Murphy
Braxton Chukka Boot (Men)
$159
Current Price $159
Aquatalia
Bernardo Water Repellent Combat Boot (Men)
$495
Current Price $495
John Varvatos
Varick Chukka Boot (Men)
$398
Current Price $398
TO BOOT NEW YORK
Christophe Chelsea Boot (Men)
$495
Current Price $495
Gordon Rush
Austin Chukka Boot (Men)
$290
Current Price $290
John Varvatos
Varick Leather Chukka Boot (Men)
$398 – $448
Current Price $398 to $448
Aquatalia
Prospero Water Resistant Chelsea Boot (Men)
$450
Current Price $450
Santoni
Easy On Chelsea Boot (Men)
$850
Current Price $850
SOREL
Slabtown '62™ Waterproof Moc Toe Boot (Men)
$175
Current Price $175
TO BOOT NEW YORK
Shelby II Chelsea Boot (Men)
$399
Current Price $399
Barbour
Readhead Chukka Boot (Men)
$220
Current Price $220
Barbour
Meays Chukka Boot (Men)
$230
Current Price $230
Red Wing
1907 Classic Moc Boot (Men)
$349.99
Current Price $349.99
Vince
Dave Chelsea Boot (Men)
$398
Current Price $398
Allen Edmonds
Chandler Chukka Boot (Men)
$525
Current Price $525
SOREL
Daystorm Horizon Gore-Tex® Weatherproof Boot (Men)
$250
Current Price $250
UGG®
Neumel Chukka Boot (Men)
$149.95
Current Price $149.95
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SCAROSSO
Leonardo Boots
$330 – $470
Current Price $330 to $470
$470
Previous Price $470
Bruno Magli
Cat Walk Chukka Boot (Men)
$350
Current Price $350
New!
Christian Louboutin
Chambeliss Chukka Boot (Men)
$1,090
Current Price $1,090
MORJAS
The Chelsea Boot (Men)
$450
Current Price $450
Santoni
Easy Chelsea Boot (Men)
$830
Current Price $830
The North Face
Bergen Waterproof Boot (Men)
$159
Current Price $159
Blundstone Footwear
Original Water Resistant Chelsea Boot (Men)
$199.95
Current Price $199.95
Alden
Burnished Chukka Boot (Men)
$682
Current Price $682
Red Wing
Blacksmith Boot (Men)
$329.99
Current Price $329.99
Mephisto
Leonardo HydroProtect Waterproof Genuine Shearling Lined Boot (Men)
$469
Current Price $469
Magnanni
Grayson Lace-Up Lug Sole Boot (Men)
$565
Current Price $565
Blundstone Footwear
Heritage Chelsea Boot (Men)
$354.95
Current Price $354.95
Nordstrom
Italian Collection Saluzzo Chukka Boot (Men)
$229.95
Current Price $229.95
BOSS
Dresletic Suede Chukka Boot (Men) (Exclusive Retailer)
$399
Current Price $399
Bruno Magli
Macy Chelsea Boot (Men)
$325
Current Price $325
TOMS
Navi Water Resistant Chukka Boot (Men)
$140
Current Price $140
BOSS
Julio Lugged Suede Chelsea Boot (Men) (Exclusive Retailer)
$250
Current Price $250
Allen Edmonds
Tompkins Boot (Men)
$550
Current Price $550
Wolverine
'1000 Mile' Plain Toe Boot (Men)
$384.95
Current Price $384.95
TO BOOT NEW YORK
Richard Chukka Boot (Men)
$450
Current Price $450
TO BOOT NEW YORK
Bedell Chelsea Boot (Men)
$595
Current Price $595
Blundstone Footwear
Classic 587 Water Resistant Chelsea Boot (Men)
$209.95
Current Price $209.95
Tecovas
The Dean Western Boot (Men)
$295
Current Price $295
Red Wing
Iron Ranger Cap Toe Boot (Men)
$349.99
Current Price $349.99
TO BOOT NEW YORK
Monaco Plain Toe Chukka Boot (Men)
$425
Current Price $425
Merrell
Thermo Chill 2 Waterproof Boot (Men)
$150
Current Price $150
Clarks® Originals
Clarks® Desert Chukka Boot (Men)
$150
Current Price $150
AllSaints
Bloom Chelsea Boot (Men)
$319
Current Price $319
Magnanni
Borazo Lug Sole Boot (Men)
$499
Current Price $499
Cole Haan
Judson Grand Chelsea Boot (Men)
$260
Current Price $260
Bruno Magli
Vestri Ankle Boot (Men)
$425
Current Price $425
TO BOOT NEW YORK
Richard Chukka Boot (Men)
$450
Current Price $450
Common Projects
Chelsea Boot (Men)
$682
Current Price $682
KLEMAN
Tonnant Lugged Plain Toe Chelsea Boot (Men)
$275
Current Price $275