Main Content

Men's Chukka Boots

Timberland Earthkeepers® 'Hookset' Canvas Chukka Boot (Men)
Timberland Earthkeepers® 'Hookset' Canvas Chukka Boot (Men)
New MarkdownTimberland Earthkeepers® 'Hookset' Canvas Chukka Boot (Men)Was: $64.95Now: $42.9033% OFF
Fred Perry 'Byron' Chukka Boot
Fred Perry 'Byron' Chukka Boot
New MarkdownFred Perry 'Byron' Chukka BootWas: $110.00Now: $65.9840% OFF
TOMS 'Classic' Chukka Boot (Men)
TOMS 'Classic' Chukka Boot (Men)
Original Penguin 'Birdie Lite' Canvas Chukka Boot (Men)
Original Penguin 'Birdie Lite' Canvas Chukka Boot (Men)
New MarkdownOriginal Penguin 'Birdie Lite' Canvas Chukka Boot (Men)Was: $140.00Now: $83.9840% OFF
Original Penguin 'Birdie Lite' Canvas Chukka Boot (Men)
Original Penguin 'Birdie Lite' Canvas Chukka Boot (Men)
New MarkdownOriginal Penguin 'Birdie Lite' Canvas Chukka Boot (Men)Was: $140.00Now: $83.9840% OFF
Tommy Bahama 'Relaxology Collection - Riker' Chukka Boot (Men)
Tommy Bahama 'Relaxology Collection - Riker' Chukka Boot (Men)
New MarkdownTommy Bahama 'Relaxology Collection - Riker' Chukka Boot (Men)Was: $138.00Now: $89.9035% OFF
Lacoste 'Sherbrooke Hi 11' Chukka Boot (Men)
Lacoste 'Sherbrooke Hi 11' Chukka Boot (Men)
Lacoste 'Zinder' Chukka Boot (Men)
Lacoste 'Zinder' Chukka Boot (Men)
New MarkdownLacoste 'Zinder' Chukka Boot (Men)Was: $160.00Now: $95.9840% OFF
Calvin Klein 'Jake' Chukka Boot (Men)
Calvin Klein 'Jake' Chukka Boot (Men)
New MarkdownCalvin Klein 'Jake' Chukka Boot (Men)Was: $140.00Now: $97.9030% OFF
Cole Haan' Ridley' Chukka Boot (Men)
Cole Haan' Ridley' Chukka Boot (Men)
New MarkdownCole Haan' Ridley' Chukka Boot (Men)Was: $188.00Now: $112.8040% OFF
Ted Baker London 'Torsdi 3' Chukka Boot (Men)
Ted Baker London 'Torsdi 3' Chukka Boot (Men)
New MarkdownTed Baker London 'Torsdi 3' Chukka Boot (Men)Was: $220.00Now: $131.9040% OFF
Ted Baker London 'Thylaar' Camo Suede Chukka (Men)
Ted Baker London 'Thylaar' Camo Suede Chukka (Men)
New MarkdownTed Baker London 'Thylaar' Camo Suede Chukka (Men)Was: $230.00Now: $137.9040% OFF
John Varvatos Star USA 'Mayfield' Laceless Chukka Boot (Men)
John Varvatos Star USA 'Mayfield' Laceless Chukka Boot (Men)
New MarkdownJohn Varvatos Star USA 'Mayfield' Laceless Chukka Boot (Men)Was: $268.00Now: $159.9040% OFF
Cole Haan 'ZeroGrand' Chukka Boot (Men)
Cole Haan 'ZeroGrand' Chukka Boot (Men)
New MarkdownCole Haan 'ZeroGrand' Chukka Boot (Men)Was: $278.00Now: $166.8040% OFF
Quoddy 'Wabanaki' Suede Chukka Boot (Men)
Quoddy 'Wabanaki' Suede Chukka Boot (Men)
New MarkdownQuoddy 'Wabanaki' Suede Chukka Boot (Men)Was: $350.00Now: $209.9840% OFF
To Boot New York 'Clarkston' Chukka Boot
To Boot New York 'Clarkston' Chukka Boot
Lottusse 'Chromex' Chukka Boot (Men)
Lottusse 'Chromex' Chukka Boot (Men)
New MarkdownLottusse 'Chromex' Chukka Boot (Men)Was: $395.00Now: $236.9840% OFF
Lottusse 'Grain' Chukka Boot (Men)
Lottusse 'Grain' Chukka Boot (Men)
Paul Smith 'Callisto' Suede Chukka Boot (Men)
Paul Smith 'Callisto' Suede Chukka Boot (Men)
New MarkdownPaul Smith 'Callisto' Suede Chukka Boot (Men)Was: $395.00Now: $264.6533% OFF
To Boot New York 'Cornell' Chukka Boot (Men)
To Boot New York 'Cornell' Chukka Boot (Men)
New MarkdownTo Boot New York 'Cornell' Chukka Boot (Men)Was: $398.00Now: $266.6633% OFF
To Boot New York 'Cornell' Chukka Boot (Men)
To Boot New York 'Cornell' Chukka Boot (Men)
Lottusse 'Martinica' Chukka Boot (Men)
Lottusse 'Martinica' Chukka Boot (Men)
New MarkdownLottusse 'Martinica' Chukka Boot (Men)Was: $525.00Now: $314.9840% OFF
Ermenegildo Zegna 'Newport' Perforated Chukka Boot (Men)
Ermenegildo Zegna 'Newport' Perforated Chukka Boot (Men)
New MarkdownErmenegildo Zegna 'Newport' Perforated Chukka Boot (Men)Was: $575.00Now: $344.9840% OFF
Giorgio Armani Perforated Suede Chukka Sneaker (Men)
Giorgio Armani Perforated Suede Chukka Sneaker (Men)
New MarkdownGiorgio Armani Perforated Suede Chukka Sneaker (Men)Was: $595.00Now: $356.9840% OFF
Giorgio Armani Woven Chukka Sneaker (Men)
Giorgio Armani Woven Chukka Sneaker (Men)
New MarkdownGiorgio Armani Woven Chukka Sneaker (Men)Was: $615.00Now: $368.9840% OFF
Alexander Wang 'Emmett' Nubuck Chukka Boot (Men)
Alexander Wang 'Emmett' Nubuck Chukka Boot (Men)
New MarkdownAlexander Wang 'Emmett' Nubuck Chukka Boot (Men)Was: $650.00Now: $389.9840% OFF
Alexander Wang 'Emmett' Chukka Boot (Men)
Alexander Wang 'Emmett' Chukka Boot (Men)
New MarkdownAlexander Wang 'Emmett' Chukka Boot (Men)Was: $695.00Now: $416.9840% OFF
Lotus 'Coventry' Suede Chukka Boot (Men)
Lotus 'Coventry' Suede Chukka Boot (Men)
Lotus 'Coventry' Suede Chukka Boot (Men)Was: $120.00Now: $69.9040% OFF
Lotus 'Addington' Chukka Boot (Men)
Lotus 'Addington' Chukka Boot (Men)
Lotus 'Addington' Chukka Boot (Men)Was: $120.00Now: $69.9040% OFF
Børn 'Axe II' Chukka Boot
Børn 'Axe II' Chukka Boot
Børn 'Axe II' Chukka BootWas: $110.00Now: $69.9035% OFF
Frank Wright 'Totton' Chukka Boot
Frank Wright 'Totton' Chukka Boot
Frank Wright 'Totton' Chukka BootWas: $120.00Now: $71.9640% OFF
Joe's 'Stomp' Suede and Denim Chukka Boot (Men)
Joe's 'Stomp' Suede and Denim Chukka Boot (Men)
Joe's 'Stomp' Suede and Denim Chukka Boot (Men)Was: $105.00Now: $72.9630% OFF
Original Penguin 'Birdie Lite' Chukka Boot (Men)
Original Penguin 'Birdie Lite' Chukka Boot (Men)
Original Penguin 'Birdie Lite' Chukka Boot (Men)Was: $155.00Now: $77.5050% OFF
J&M 1850 'Burchfield' Chukka Boot (Online Only)
J&M 1850 'Burchfield' Chukka Boot (Online Only)
Bed Stu 'Draco' Chukka Boot (Men)
Bed Stu 'Draco' Chukka Boot (Men)
Bed Stu 'Draco' Chukka Boot (Men)Was: $135.00Now: $80.9640% OFF
Frank Wright 'Smith' Chukka Boot
Frank Wright 'Smith' Chukka Boot
Frank Wright 'Smith' Chukka BootWas: $140.00Now: $83.9640% OFF
Tommy Bahama 'Relaxology Collection - Riker' Chukka Boot (Men)
Tommy Bahama 'Relaxology Collection - Riker' Chukka Boot (Men)
Dunham 'REVdash' Chukka Boot (Men)
Dunham 'REVdash' Chukka Boot (Men)
Dunham 'REVdash' Chukka Boot (Men)Was: $150.00Now: $89.9640% OFF
Anatomic & Co 'Furnas' Chukka Boot (Men)
Anatomic & Co 'Furnas' Chukka Boot (Men)
Dr. Scholl's Original Collection 'Da Capo' Chukka Boot
Dr. Scholl's Original Collection 'Da Capo' Chukka Boot
UGG® Australia 'Alin' Chukka Boot
UGG® Australia 'Alin' Chukka Boot
UGG® Australia 'Alin' Chukka BootWas: $149.95Now: $99.9033% OFF
John Varvatos Star USA 'Hipster' Suede Chukka Boot (Men)
John Varvatos Star USA 'Hipster' Suede Chukka Boot (Men)
John Varvatos Star USA 'Hipster' Chukka Boot (Men)
John Varvatos Star USA 'Hipster' Chukka Boot (Men)
Joe's 'Ample' Suede Chukka Boot (Men)
Joe's 'Ample' Suede Chukka Boot (Men)
Joe's 'Ample' Suede Chukka Boot (Men)Was: $160.00Now: $111.9630% OFF
UGG® Australia 'Brompton' Chukka Boot (Men)
UGG® Australia 'Brompton' Chukka Boot (Men)
Joe's 'Slick' Suede Chukka Boot (Men)
Joe's 'Slick' Suede Chukka Boot (Men)
Joe's 'Slick' Suede Chukka Boot (Men)Was: $175.00Now: $121.9630% OFF
Andrew Marc 'Haven' Chukka Boot (Men)
Andrew Marc 'Haven' Chukka Boot (Men)
Andrew Marc 'Haven' Chukka Boot (Men)Was: $178.00Now: $124.6030% OFF
Cole Haan 'Paul' Chukka Boot
Cole Haan 'Paul' Chukka Boot
Carlo Pazolini Suede Chukka Boot (Men)
Carlo Pazolini Suede Chukka Boot (Men)
Carlo Pazolini Suede Chukka Boot (Men)Was: $225.00Now: $134.9640% OFF
Boemos Suede Chukka Boot (Men)
Boemos Suede Chukka Boot (Men)
Boemos Suede Chukka Boot (Men)Was: $205.00Now: $137.3533% OFF
Andrew Marc 'Dorchester' Suede Chukka Boot (Men)
Andrew Marc 'Dorchester' Suede Chukka Boot (Men)
Andrew Marc 'Dorchester' Suede Chukka Boot (Men)Was: $198.00Now: $137.9030% OFF
Dune London 'Columbo' Chukka Boot (Men)
Dune London 'Columbo' Chukka Boot (Men)
Dune London 'Columbo' Chukka Boot (Men)Was: $179.00Now: $142.9620% OFF
Cole Haan 'Glenn' Chukka Boot
Cole Haan 'Glenn' Chukka Boot
Cole Haan 'Glenn' Chukka BootWas: $228.00Now: $149.9033% OFF
Cole Haan 'Glenn' Chukka Boot
Cole Haan 'Glenn' Chukka Boot
Maison Forte 'Badlands' Chukka Boot (Men)
Maison Forte 'Badlands' Chukka Boot (Men)
Maison Forte 'Badlands' Chukka Boot (Men)Was: $240.00Now: $159.9033% OFF
Cole Haan 'Cambridge' Chukka Boot (Men)
Cole Haan 'Cambridge' Chukka Boot (Men)
Trask 'Gulch' Chukka Boot
Trask 'Gulch' Chukka Boot
Trask 'Gulch' Chukka BootWas: $265.00Now: $179.9030% OFF
Trask 'Gulch' Chukka Boot
Trask 'Gulch' Chukka Boot
Trask 'Gulch' Chukka BootWas: $295.00Now: $179.9035% OFF
Bacco Bucci 'Vialli' Chukka Boot (Men)
Bacco Bucci 'Vialli' Chukka Boot (Men)
Bacco Bucci 'Vialli' Chukka Boot (Men)Was: $265.00Now: $184.9630% OFF
Lloyd 'Spider' Chukka Boot
Lloyd 'Spider' Chukka Boot
Lloyd 'Spider' Chukka BootWas: $269.00Now: $199.9025% OFF
Timberland Boot Company 'Wodehouse Lost History' Chukka Boot (Men) (Nordstrom Exclusive)
Timberland Boot Company 'Wodehouse Lost History' Chukka Boot (Men) (Nordstrom Exclusive)
Timberland 'Coulter Collection' Chukka Boot (Men)
Timberland 'Coulter Collection' Chukka Boot (Men)
Timberland 'Coulter Collection' Chukka Boot (Men)Was: $395.00Now: $265.9033% OFF
Gorilla USA Chukka Boot (Men)
Gorilla USA Chukka Boot (Men)
Deer Stags 'Seattle' Leather Chukka Boot (Men)
Deer Stags 'Seattle' Leather Chukka Boot (Men)
Deer Stags 'Mean' Leather Chukka Boot (Men)
Deer Stags 'Mean' Leather Chukka Boot (Men)
Steve Madden 'Halloway' Canvas Chukka Boot (Men)
Steve Madden 'Halloway' Canvas Chukka Boot (Men)
Volcom 'Del Mesa' Suede Chukka Boot (Men)
Volcom 'Del Mesa' Suede Chukka Boot (Men)
Ben Sherman 'Victor' Suede & Leather Chukka Boot (Men)
Ben Sherman 'Victor' Suede & Leather Chukka Boot (Men)
Ben Sherman 'Victor' Suede & Canvas Chukka Boot (Men)
Ben Sherman 'Victor' Suede & Canvas Chukka Boot (Men)
ALDO 'Nyah' Leather Chukka Boot (Men)
ALDO 'Nyah' Leather Chukka Boot (Men)
Volcom 'Del Mesa' Chukka Boot (Men)
Volcom 'Del Mesa' Chukka Boot (Men)
Steve Madden 'Handler' Chukka Boot (Men)
Steve Madden 'Handler' Chukka Boot (Men)
Steve Madden 'Harken' Leather Chukka Boot (Men)
Steve Madden 'Harken' Leather Chukka Boot (Men)
CLAE 'Strayhorn' Chukka Boot
CLAE 'Strayhorn' Chukka Boot
Ariat 'Holbrook' Chukka Boot (Men)
Ariat 'Holbrook' Chukka Boot (Men)
UGG® Australia 'Freamon' Suede Chukka Boot (Men)
UGG® Australia 'Freamon' Suede Chukka Boot (Men)
Timberland Earthkeepers® 'Brookpark' Suede Chukka Boot (Men)
Timberland Earthkeepers® 'Brookpark' Suede Chukka Boot (Men)
Hush Puppies® 'Bridgeport' Boot (Men)
Hush Puppies® 'Bridgeport' Boot (Men)
Clarks® Originals 'Stinson' Moc Toe Chukka Boot
Clarks® Originals 'Stinson' Moc Toe Chukka Boot
Sperry Top-Sider® 'Authentic Original' Chukka Boot (Men)
Sperry Top-Sider® 'Authentic Original' Chukka Boot (Men)
Børn 'Asten' Chukka Boot (Men)
Børn 'Asten' Chukka Boot (Men)
Hush Puppies 'Aquaice Wallaboot' Chukka Boot (Men)
Hush Puppies 'Aquaice Wallaboot' Chukka Boot (Men)
TOMS 'Classic' Suede Chukka Boot (Men)
TOMS 'Classic' Suede Chukka Boot (Men)
Florsheim 'Doon' Chukka Boot (Men)
Florsheim 'Doon' Chukka Boot (Men)
Florsheim 'Doon' Chukka Boot (Men)
Florsheim 'Doon' Chukka Boot (Men)
1901 'Hayward' Chukka Boot (Men)
1901 'Hayward' Chukka Boot (Men)
Rockport 'RocSports Zonecush' Chukka Boot (Men)
Rockport 'RocSports Zonecush' Chukka Boot (Men)

No items match all your filter selections.

Clear all to see unfiltered results.