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Men's Boots

Boot up: The Chelsea. Men's boot guide.

The timeless Chelsea boot takes you from morning meetings to long nights out in a single, well-heeled step.

SHOP: DRESS BOOTS

Men's Boots

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Steve Madden 'Bennyy' Chelsea Boot (Men)
PRICE MATCHEDSteve Madden 'Bennyy' Chelsea Boot (Men)Was: $110.00Now: $77.0030% OFF
(1)
Frank Wright 'Totton' Chukka Boot
Frank Wright 'Totton' Chukka BootWas: $120.00Now: $69.9640% OFF
(1)
Frank Wright 'Mortimer II' Plain Toe Boot
Frank Wright 'Mortimer II' Plain Toe BootWas: $130.00Now: $77.9640% OFF
(2)
Bed Stu 'Bryden' Boot (Online Only) (Men)
PRICE MATCHEDBed Stu 'Bryden' Boot (Online Only) (Men)Was: $110.00Now: $86.4220% OFF
(3)
Sebago 'Tremont' Chukka Boot
PRICE MATCHEDSebago 'Tremont' Chukka BootWas: $165.00Now: $60.8060% OFF
(3)
Clarks® Originals 'Desert' Boot (Online Only) (Men)
PRICE MATCHEDClarks® Originals 'Desert' Boot (Online Only) (Men)Was: $120.00Now: $51.1355% OFF
Eastland 'Wyatt 1955' Moc Toe Boot (Men)
Eastland 'Wyatt 1955' Moc Toe Boot (Men)Was: $145.00Now: $99.9630% OFF
Wolverine 'Carlos' Chukka Boot (Men)
PRICE MATCHEDWolverine 'Carlos' Chukka Boot (Men)Was: $145.00Now: $79.9945% OFF
Dr. Martens '1460' Boot (Men)
PRICE MATCHEDDr. Martens '1460' Boot (Men)Was: $125.00Now: $85.8230% OFF
Calvin Klein 'Carlisle' Chelsea Boot (Men)
PRICE MATCHEDCalvin Klein 'Carlisle' Chelsea Boot (Men)Was: $130.00Now: $97.5025% OFF
Dr. Martens '1460' Boot (Men)
PRICE MATCHEDDr. Martens '1460' Boot (Men)Was: $125.00Now: $79.7935% OFF
Kickers 'Darius' Plain Toe Boot
Kickers 'Darius' Plain Toe BootWas: $167.00Now: $83.4950% OFF
Clarks® Originals 'Stinson' Moc Toe Chukka Boot
PRICE MATCHEDClarks® Originals 'Stinson' Moc Toe Chukka BootWas: $110.00Now: $71.5735% OFF
Dr. Martens '1460' Boot
PRICE MATCHEDDr. Martens '1460' BootWas: $120.00Now: $94.5020% OFF
(1)
Kickers 'Darius' Plain Toe Boot
Kickers 'Darius' Plain Toe BootWas: $167.00Now: $79.9750% OFF
Dr. Martens 'Original 1460' Boot (Men)
PRICE MATCHEDDr. Martens 'Original 1460' Boot (Men)Was: $120.00Now: $93.8220% OFF
Timberland Earthkeepers® 'City Lite' Chukka Boot
PRICE MATCHEDTimberland Earthkeepers® 'City Lite' Chukka BootWas: $120.00Now: $80.7633% OFF
Clarks® 'Senner Drive' Chukka Boot (Men)
PRICE MATCHEDClarks® 'Senner Drive' Chukka Boot (Men)Was: $99.95Now: $69.9930% OFF
Sebago 'Thayer' Chukka Boot
PRICE MATCHEDSebago 'Thayer' Chukka BootWas: $155.00Now: $86.99 - $108.9940% OFF
J.D. Fisk 'Antwerp' Cap Toe Boot
New MarkdownJ.D. Fisk 'Antwerp' Cap Toe BootWas: $189.00Now: $93.9650% OFF
Bugatchi 'Vail' Chukka Boot (Men)
Bugatchi 'Vail' Chukka Boot (Men)Was: $210.00Now: $99.9650% OFF
(7)
Kickers 'River 6' Chukka Boot
Kickers 'River 6' Chukka BootWas: $163.00Now: $89.9645% OFF
(1)
Sebago 'Thayer' Chukka Boot
PRICE MATCHEDSebago 'Thayer' Chukka BootWas: $155.00Now: $86.9940% OFF
Ben Sherman 'Aberdeen' Chukka Boot (Men)
Ben Sherman 'Aberdeen' Chukka Boot (Men)Was: $130.00Now: $77.9840% OFF
Sperry Top-Sider® 'Harbor' Canvas Chukka Boot
PRICE MATCHEDSperry Top-Sider® 'Harbor' Canvas Chukka BootWas: $99.95Now: $54.9945% OFF
Dr. Martens 'Beckett' Boot
PRICE MATCHEDDr. Martens 'Beckett' BootWas: $200.00Now: $69.9965% OFF
Caterpillar 'Haverhill' Chukka Boot (Men)
PRICE MATCHEDCaterpillar 'Haverhill' Chukka Boot (Men)Was: $150.00Now: $98.9833% OFF
Clarks® 'Senner Ave' Chukka Boot   (Men)
PRICE MATCHEDClarks® 'Senner Ave' Chukka Boot (Men)Was: $99.95Now: $77.0720% OFF
Caterpillar 'Graft' Plain Toe Boot
PRICE MATCHEDCaterpillar 'Graft' Plain Toe BootWas: $89.95Now: $66.2725% OFF
John Varvatos Star USA 'Redding' Chukka Boot
John Varvatos Star USA 'Redding' Chukka BootWas: $198.00Now: $98.9850% OFF
Quiksilver 'Bishop' Chukka Boot
Quiksilver 'Bishop' Chukka BootWas: $110.00Now: $54.9850% OFF
Roberto Vasi 'Samuel' Boot
Roberto Vasi 'Samuel' BootWas: $129.95Now: $87.0733% OFF
J SHOES 'Selby' Chukka Boot
J SHOES 'Selby' Chukka BootWas: $150.00Now: $99.9033% OFF
(1)
Clarks® Originals 'Vulco Spear' Chukka Boot (Men)
PRICE MATCHEDClarks® Originals 'Vulco Spear' Chukka Boot (Men)Was: $135.00Now: $89.9933% OFF
Clarks® Originals 'Vulco Spear' Chukka Boot (Men)
PRICE MATCHEDClarks® Originals 'Vulco Spear' Chukka Boot (Men)Was: $135.00Now: $89.9933% OFF
Joe's 'Cade' Chukka Boot (Men)
Joe's 'Cade' Chukka Boot (Men)Was: $120.00Now: $94.0020% OFF
Caterpillar 'Edgar' Chukka Boot (Men)
PRICE MATCHEDCaterpillar 'Edgar' Chukka Boot (Men)Was: $150.00Now: $76.9945% OFF
Roberto Vasi 'Hudson' Camo Chukka Boot
Roberto Vasi 'Hudson' Camo Chukka BootWas: $130.00Now: $87.0733% OFF

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