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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)
New MarkdownSteve Madden 'Bennyy' Chelsea Boot (Men)Was: $110.00Now: $77.0030% OFF
(1)
Wolverine 'Carlos' Chukka Boot (Men)
New MarkdownWolverine 'Carlos' Chukka Boot (Men)Was: $145.00Now: $79.9945% OFF
Wolverine '1883 - Orville' Chukka Boot
New MarkdownWolverine '1883 - Orville' Chukka BootWas: $135.00Now: $100.2325% OFF
Wolverine '1883 - Shindell' Moc Toe Boot
New MarkdownWolverine '1883 - Shindell' Moc Toe BootWas: $135.00Now: $101.1325% OFF
Tsubo 'Halian' Chukka Boot
New MarkdownTsubo 'Halian' Chukka BootWas: $184.95Now: $106.9940% OFF
Vince Camuto 'Carmine' Suede Chelsea Boot (Men)
New MarkdownVince Camuto 'Carmine' Suede Chelsea Boot (Men)Was: $120.00Now: $106.9910% OFF
Steve Madden 'Restorr' Wingtip Boot (Men)
New MarkdownSteve Madden 'Restorr' Wingtip Boot (Men)Was: $125.00Now: $107.2910% OFF
Steve Madden 'Restorr' Wingtip Boot (Men)
New MarkdownSteve Madden 'Restorr' Wingtip Boot (Men)Was: $125.00Now: $107.2910% OFF
(1)
Florsheim 'Jet' Chukka Boot
New MarkdownFlorsheim 'Jet' Chukka BootWas: $135.00Now: $114.7515% OFF
ohw? 'Louis' Two Tone Suede Moc Toe Boot (Men)
New Markdownohw? 'Louis' Two Tone Suede Moc Toe Boot (Men)Was: $200.00Now: $128.9635% OFF
John Varvatos Collection 'Dylan' Chukka Boot
New MarkdownJohn Varvatos Collection 'Dylan' Chukka BootWas: $398.00Now: $129.9965% OFF
Vince Camuto 'Sergio' Chelsea Boot (Men)
New MarkdownVince Camuto 'Sergio' Chelsea Boot (Men)Was: $150.00Now: $134.9910% OFF
Cole Haan 'LunarGrand' Moc Toe Boot (Men)
New MarkdownCole Haan 'LunarGrand' Moc Toe Boot (Men)Was: $228.00Now: $149.9033% OFF
Sperry Top-Sider® 'Bahama' Moc Toe Boot
Sperry Top-Sider® 'Bahama' Moc Toe BootWas: $84.95Now: $42.4750% OFF
Minnetonka Fringe Boot (Men)
Minnetonka Fringe Boot (Men)Was: $49.95Now: $45.955% OFF
Bogs 'Tillamook Bay' Rain Boot   (Men)
Bogs 'Tillamook Bay' Rain Boot (Men)Was: $89.95Now: $49.5045% OFF
Sperry Top-Sider® 'Bahama' Boot
Sperry Top-Sider® 'Bahama' BootWas: $99.95Now: $49.9650% OFF
(2)
Quiksilver 'Bishop' Chukka Boot
Quiksilver 'Bishop' Chukka BootWas: $110.00Now: $54.9850% OFF
Sperry Top-Sider® 'Harbor' Canvas Chukka Boot
Sperry Top-Sider® 'Harbor' Canvas Chukka BootWas: $99.95Now: $54.9945% OFF
Caterpillar 'Transform' Boot (Men)
Caterpillar 'Transform' Boot (Men)Was: $79.95Now: $60.0025% OFF
G.H. Bass & Co. 'Plano' Plain Toe Boot
G.H. Bass & Co. 'Plano' Plain Toe BootWas: $84.95Now: $60.5025% OFF
Sebago 'Tremont' Chukka Boot
Sebago 'Tremont' Chukka BootWas: $165.00Now: $60.8060% OFF
(3)
Caterpillar 'Graft' Plain Toe Boot
Caterpillar 'Graft' Plain Toe BootWas: $89.95Now: $66.2725% OFF
Frank Wright 'Totton' Chukka Boot
Frank Wright 'Totton' Chukka BootWas: $120.00Now: $69.9640% OFF
(1)
Clarks® 'Senner Drive' Chukka Boot (Men)
Clarks® 'Senner Drive' Chukka Boot (Men)Was: $99.95Now: $69.9930% OFF
Dr. Martens 'Beckett' Boot
Dr. Martens 'Beckett' BootWas: $200.00Now: $69.9965% OFF
Clarks® Originals 'Stinson' Moc Toe Chukka Boot
Clarks® Originals 'Stinson' Moc Toe Chukka BootWas: $110.00Now: $71.5735% OFF
Ariat 'Holbrook' Chukka Boot (Men)
Ariat 'Holbrook' Chukka Boot (Men)Was: $99.95Now: $76.9920% OFF
Clarks® 'Senner Ave' Chukka Boot   (Men)
Clarks® 'Senner Ave' Chukka Boot (Men)Was: $99.95Now: $77.0720% OFF
Ben Sherman 'Aberdeen' Chukka Boot (Men)
Ben Sherman 'Aberdeen' Chukka Boot (Men)Was: $130.00Now: $77.9840% OFF
Kickers 'Darius' Plain Toe Boot
Kickers 'Darius' Plain Toe BootWas: $167.00Now: $79.9750% OFF
Kickers 'Darius' Plain Toe Boot
Kickers 'Darius' Plain Toe BootWas: $167.00Now: $83.4950% OFF
Bed Stu 'Burst' Boot (Online Only) (Men)
Bed Stu 'Burst' Boot (Online Only) (Men)Was: $135.00Now: $84.9935% OFF
Dr. Martens '1460' Boot (Men)
Dr. Martens '1460' Boot (Men)Was: $125.00Now: $85.8230% OFF
Bed Stu 'Bryden' Boot (Online Only)
Bed Stu 'Bryden' Boot (Online Only)Was: $110.00Now: $86.4220% OFF
Bed Stu 'Bryden' Boot (Online Only) (Men)
Bed Stu 'Bryden' Boot (Online Only) (Men)Was: $110.00Now: $86.4220% OFF
(3)
Sebago 'Thayer' Chukka Boot
Sebago 'Thayer' Chukka BootWas: $155.00Now: $86.9940% OFF
Sebago 'Gibraltar' Moc Toe Boot
Sebago 'Gibraltar' Moc Toe BootWas: $155.00Now: $86.9940% OFF
Sebago 'Thayer' Chukka Boot
Sebago 'Thayer' Chukka BootWas: $155.00Now: $86.99 - $108.9940% OFF
Roberto Vasi 'Hudson' Camo Chukka Boot
Roberto Vasi 'Hudson' Camo Chukka BootWas: $130.00Now: $87.0733% OFF
Roberto Vasi 'Samuel' Boot
Roberto Vasi 'Samuel' BootWas: $129.95Now: $87.0733% OFF
Eastland 'Porter 1955' Cap Toe Boot (Men)
Eastland 'Porter 1955' Cap Toe Boot (Men)Was: $135.00Now: $89.9633% OFF
Kickers 'River 6' Chukka Boot
Kickers 'River 6' Chukka BootWas: $163.00Now: $89.9645% OFF
(1)
Dr. Martens 'Original 1460' Boot (Men)
Dr. Martens 'Original 1460' Boot (Men)Was: $120.00Now: $93.8220% OFF
Joe's 'Cade' Chukka Boot (Men)
Joe's 'Cade' Chukka Boot (Men)Was: $120.00Now: $94.0020% OFF
Dr. Martens '1460' Boot
Dr. Martens '1460' BootWas: $120.00Now: $94.5020% OFF
(1)
Caterpillar 'Vinson' Boot (Men)
Caterpillar 'Vinson' Boot (Men)Was: $154.00Now: $94.9935% OFF
Caterpillar 'Vinson' Boot (Men)
Caterpillar 'Vinson' Boot (Men)Was: $154.00Now: $94.9935% OFF
(2)
Rockport 'Ledge Hill' Chukka Boot
Rockport 'Ledge Hill' Chukka BootWas: $145.00Now: $96.9633% OFF
(2)
John Varvatos Star USA 'Redding' Chukka Boot
John Varvatos Star USA 'Redding' Chukka BootWas: $198.00Now: $98.9850% OFF
John Varvatos Star USA 'Hipster' Chukka Boot
John Varvatos Star USA 'Hipster' Chukka BootWas: $198.00Now: $98.9850% OFF
(6)
J SHOES 'Selby' Chukka Boot
J SHOES 'Selby' Chukka BootWas: $150.00Now: $99.9033% OFF
(1)
Ariat 'Radcliffe' Boot
Ariat 'Radcliffe' BootWas: $169.95Now: $99.9640% OFF
Eastland 'Wyatt 1955' Moc Toe Boot (Men)
Eastland 'Wyatt 1955' Moc Toe Boot (Men)Was: $145.00Now: $99.9630% OFF
Bugatchi 'Vail' Chukka Boot (Men)
Bugatchi 'Vail' Chukka Boot (Men)Was: $210.00Now: $99.9650% OFF
(7)
Andrew Marc 'Dorchester' Chukka Boot (Men)
Andrew Marc 'Dorchester' Chukka Boot (Men)Was: $178.00Now: $99.9940% OFF
Andrew Marc 'Dorchester' Chukka Boot (Men)
Andrew Marc 'Dorchester' Chukka Boot (Men)Was: $178.00Now: $99.9940% OFF
Kenneth Cole Reaction 'Hit Men' Cap Toe Boot
Kenneth Cole Reaction 'Hit Men' Cap Toe BootWas: $148.00Now: $103.6030% OFF
Kenneth Cole Reaction 'Hit Men' Cap Toe Boot
Kenneth Cole Reaction 'Hit Men' Cap Toe BootWas: $148.00Now: $103.6030% OFF
(14)
Caterpillar 'Haverhill' Chukka Boot (Men)
Caterpillar 'Haverhill' Chukka Boot (Men)Was: $150.00Now: $103.7530% OFF
Tsubo 'Halian' Chukka Boot
Tsubo 'Halian' Chukka BootWas: $194.95Now: $106.9945% OFF
Tsubo 'Halian' Chukka Boot
Tsubo 'Halian' Chukka BootWas: $184.95Now: $106.9940% OFF
Caterpillar 'Morrison' Cap Toe Boot (Men)
Caterpillar 'Morrison' Cap Toe Boot (Men)Was: $140.00Now: $108.7820% OFF
(5)
Bed Stu 'Patriot' Cap Toe Boot
Bed Stu 'Patriot' Cap Toe BootWas: $145.00Now: $108.7925% OFF
(5)
SeaVees '12/67 Three Eye' Chukka Boot
SeaVees '12/67 Three Eye' Chukka BootWas: $178.00Now: $109.9035% OFF
(2)
Rockport 'RocSports Rugged' Moc Toe Boot
Rockport 'RocSports Rugged' Moc Toe BootWas: $160.00Now: $109.9630% OFF
(2)
Bugatchi 'Alta' Wingtip Boot (Men)
Bugatchi 'Alta' Wingtip Boot (Men)Was: $185.00 - $210.00Now: $110.9640% OFF
J SHOES 'Monarch' Chukka Boot
J SHOES 'Monarch' Chukka BootWas: $198.00Now: $111.0040% OFF
Teva 'Riva Winter' Boot (Online Only)
Teva 'Riva Winter' Boot (Online Only)Was: $160.00Now: $112.9925% OFF
(1)
Caterpillar 'Abe' Boot (Men)
Caterpillar 'Abe' Boot (Men)Was: $145.00Now: $114.0020% OFF
Caterpillar 'Orson' Boot (Men) (Online Only)
Caterpillar 'Orson' Boot (Men) (Online Only)Was: $160.00Now: $116.1225% OFF

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