Main Content

Men's Boots

Fall chukka boots for men.

This month, get to know the rugged roots and urbane cool of the chukka boot.

Fall chukka boots for men.

Artisan details make sophisticated work of these streetwise trekkers.

Fall chukka boots for men.

White soles and classic construction evoke essential retro cool.

Fall chukka boots for men.

With supple suede and cushioning crepe soles, these boots keep comfort in mind.

Men's Boots

NARROW BY:
Ariat 'Radcliffe' Boot
New MarkdownAriat 'Radcliffe' BootWas: $169.95Now: $99.9640% OFF
Bugatchi 'Northstar' Cap Toe Boot (Men)
New MarkdownBugatchi 'Northstar' Cap Toe Boot (Men)Was: $230.00Now: $126.9645% OFF
Bugatchi 'Northstar' Cap Toe Boot (Men)
New MarkdownBugatchi 'Northstar' Cap Toe Boot (Men)Was: $230.00Now: $126.9645% OFF
Cole Haan 'Glenn' Chukka Boot
New MarkdownCole Haan 'Glenn' Chukka BootWas: $228.00Now: $159.9630% OFF
Cole Haan 'LunarGrand' Chukka Boot (Men)
New MarkdownCole Haan 'LunarGrand' Chukka Boot (Men)Was: $278.00Now: $159.9640% OFF
Red Wing Suede Chukka Boot (Men)
New MarkdownRed Wing Suede Chukka Boot (Men)Was: $260.00Now: $169.9035% OFF
Red Wing Suede Chukka Boot (Men)
New MarkdownRed Wing Suede Chukka Boot (Men)Was: $260.00Now: $169.9035% OFF
Red Wing Moc Toe Boot (Men)
New MarkdownRed Wing Moc Toe Boot (Men)Was: $260.00Now: $169.9035% OFF
Red Wing Suede Moc Toe Boot (Men)
New MarkdownRed Wing Suede Moc Toe Boot (Men)Was: $260.00Now: $169.9035% OFF
Red Wing Suede Chukka Boot (Men)
New MarkdownRed Wing Suede Chukka Boot (Men)Was: $260.00Now: $169.9035% OFF
Lucchese 'Jesse' Western Boot (Men)
New MarkdownLucchese 'Jesse' Western Boot (Men)Was: $350.00Now: $279.9020% OFF
Sperry Top-Sider® 'Bahama' Moc Toe Boot
Sperry Top-Sider® 'Bahama' Moc Toe BootWas: $84.95Now: $42.4750% OFF
Sperry Top-Sider® 'Bahama' Moc Toe Boot
Sperry Top-Sider® 'Bahama' Moc Toe BootWas: $89.95Now: $44.9650% OFF
(2)
Sperry Top-Sider® 'Bahama' Boot
Sperry Top-Sider® 'Bahama' BootWas: $99.95Now: $49.9650% OFF
(2)
Kickers 'Edouard' Chukka Boot
Kickers 'Edouard' Chukka BootWas: $156.00Now: $77.9850% OFF
(2)
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
Sperry Top-Sider® 'Gold Cup' Chukka Boot
Sperry Top-Sider® 'Gold Cup' Chukka BootWas: $170.00Now: $84.9850% OFF
Roberto Vasi 'Hudson' Camo Chukka Boot
Roberto Vasi 'Hudson' Camo Chukka BootWas: $130.00Now: $87.0733% OFF
Polo Ralph Lauren 'Maurice' Plain Toe Boot
Polo Ralph Lauren 'Maurice' Plain Toe BootWas: $179.00Now: $89.4950% OFF
Kickers 'River 6' Chukka Boot
Kickers 'River 6' Chukka BootWas: $163.00Now: $89.9645% OFF
(1)
Tsubo 'Halian' Chukka Boot
Tsubo 'Halian' Chukka BootWas: $184.95Now: $92.9050% OFF
Dr. Martens 'Nero' Suede Boot
Dr. Martens 'Nero' Suede BootWas: $140.00Now: $93.8033% OFF
(1)
Joe's 'Cade' Chukka Boot (Men)
Joe's 'Cade' Chukka Boot (Men)Was: $120.00Now: $94.0020% OFF
UGG® Australia 'Via Lungarno' Chukka Boot
UGG® Australia 'Via Lungarno' Chukka BootWas: $189.95Now: $94.9650% OFF
(4)
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)
Bugatchi 'Vail' Chukka Boot (Men)
Bugatchi 'Vail' Chukka Boot (Men)Was: $210.00Now: $99.9650% OFF
(7)
UGG® Australia 'Via Lungarno' Chukka Boot
UGG® Australia 'Via Lungarno' Chukka BootWas: $189.95Now: $109.9740% OFF
Tommy Bahama 'Editso' Plain Toe Boot
Tommy Bahama 'Editso' Plain Toe BootWas: $198.00Now: $116.9640% OFF
(1)
Tommy Bahama 'Editso' Plain Toe Boot
Tommy Bahama 'Editso' Plain Toe BootWas: $198.00Now: $116.9640% OFF
(5)
Eastland 'Norwich 1955' Moc Toe Boot
Eastland 'Norwich 1955' Moc Toe BootWas: $215.00Now: $128.9640% OFF
Cole Haan 'Paul' Chukka Boot
Cole Haan 'Paul' Chukka BootWas: $198.00Now: $129.9033% OFF
(16)
Gordon Rush 'Patterson' Chelsea Boot
Gordon Rush 'Patterson' Chelsea BootWas: $265.00Now: $132.4950% OFF
Rogue Plain Toe Boot
Rogue Plain Toe BootWas: $224.95Now: $134.9640% OFF
(1)
Rogue 'Chuck 2' Chukka Boot
Rogue 'Chuck 2' Chukka BootWas: $195.00Now: $136.5030% OFF
Rogue 'Kongo 1' Boot
Rogue 'Kongo 1' BootWas: $195.00Now: $136.5030% OFF
(1)
Rogue 'Drakon' Chukka Boot
Rogue 'Drakon' Chukka BootWas: $198.00Now: $138.6030% OFF
Dr. Martens 'Bentley' Boot
Dr. Martens 'Bentley' BootWas: $210.00Now: $139.9633% OFF
(6)
PIKOLINOS 'Barcelona' Suede Boot
PIKOLINOS 'Barcelona' Suede BootWas: $190.00Now: $139.9625% OFF
(1)
Andrew Marc 'Gotham' Plain Toe Boot (Men)
Andrew Marc 'Gotham' Plain Toe Boot (Men)Was: $218.00Now: $141.7035% OFF
(1)
Boemos Plain Toe Boot (Men)
Boemos Plain Toe Boot (Men)Was: $221.00Now: $148.0733% OFF
Broken Homme 'James' Round Toe Boot
Broken Homme 'James' Round Toe BootWas: $299.00Now: $149.4950% OFF
Rogue 'Platon' Wingtip Boot
Rogue 'Platon' Wingtip BootWas: $224.95Now: $149.9633% OFF
Boemos Suede Chelsea Boot (Men)
Boemos Suede Chelsea Boot (Men)Was: $226.00Now: $151.4233% OFF
Blackstone 'AM 12' Cap Toe Boot (Men)
Blackstone 'AM 12' Cap Toe Boot (Men)Was: $257.00Now: $154.2040% OFF
ECCO 'Roxton' Boot
ECCO 'Roxton' BootWas: $239.95Now: $159.9033% OFF
(3)
J.D. Fisk 'Inverness' Round Toe Boot
J.D. Fisk 'Inverness' Round Toe BootWas: $299.00Now: $159.9645% OFF
(1)
UGG® Australia 'Rockville II' Boot (Men)
UGG® Australia 'Rockville II' Boot (Men)Was: $249.95Now: $159.9735% OFF
(24)
Rogue 'Bud' Chukka Boot
Rogue 'Bud' Chukka BootWas: $235.00Now: $164.5030% OFF
Rogue 'Kuaka' Boot
Rogue 'Kuaka' BootWas: $275.00Now: $164.9640% OFF
Bacco Bucci 'Cotton' Boot (Men)
Bacco Bucci 'Cotton' Boot (Men)Was: $255.00Now: $164.9635% OFF
(1)
Andrew Marc 'Willets' Chukka Boot (Men)
Andrew Marc 'Willets' Chukka Boot (Men)Was: $298.00Now: $178.8040% OFF
John Varvatos Star USA 'Townshend' Wingtip Boot
John Varvatos Star USA 'Townshend' Wingtip BootWas: $328.00Now: $179.9645% OFF
Lloyd 'Hengelo' Chukka Boot
Lloyd 'Hengelo' Chukka BootWas: $269.00Now: $179.9633% OFF
(1)
Rogue 'Zeppole' Boot
Rogue 'Zeppole' BootWas: $275.00Now: $192.5030% OFF
(1)
Blackstone 'AM 08' Boot (Men)
Blackstone 'AM 08' Boot (Men)Was: $329.00Now: $197.4040% OFF
Bacco Bucci 'Rockey' Cap Toe Boot (Men)
Bacco Bucci 'Rockey' Cap Toe Boot (Men)Was: $295.00Now: $198.9633% OFF
Lloyd 'Sullivan' Zip Boot
Lloyd 'Sullivan' Zip BootWas: $319.00Now: $219.9630% OFF
Lloyd 'Stanton' Chukka Boot
Lloyd 'Stanton' Chukka BootWas: $319.00Now: $219.9630% OFF
Lucchese Ostrich & Calfskin Cowboy Boot (Men)
Lucchese Ostrich & Calfskin Cowboy Boot (Men)Was: $320.00Now: $224.9030% OFF
(3)
Lottusse Wingtip Boot
Lottusse Wingtip BootWas: $480.00Now: $239.9650% OFF
Trask 'Glacier' Boot
Trask 'Glacier' BootWas: $385.00Now: $249.9635% OFF
(1)

No items match all your filter selections.

Clear all to see unfiltered results.