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Men's Boots

The new chukka boot: refine your style.

Fresh details modernize the classic chukka: oiled leather and tire-tread soles or soft suede with sneaker styling.

SHOP: CHUKKA BOOTS

Men's Boots

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Minnetonka Fringe Boot (Men)
Minnetonka Fringe Boot (Men)
Deer Stags 'Bristol' Cap Toe Boot (Men)
Deer Stags 'Bristol' Cap Toe Boot (Men)
Deer Stags 'Bristol' Cap Toe Boot (Men)Was: $79.95Now: $59.9025% OFF
Deer Stags 'Mean' Leather Chukka Boot (Men)
Deer Stags 'Mean' Leather Chukka Boot (Men)
Price MatchedDeer Stags 'Mean' Leather Chukka Boot (Men)Was: $79.95Now: $60.0025% OFF
1901 'Calgary' Chukka Boot (Men)
1901 'Calgary' Chukka Boot (Men)
New Markdown1901 'Calgary' Chukka Boot (Men)Was: $110.00Now: $65.9040% OFF
1901 'Calgary' Chukka Boot (Men)
1901 'Calgary' Chukka Boot (Men)
Børn 'Asten' Chukka Boot (Men)
Børn 'Asten' Chukka Boot (Men)
Børn 'Asten' Chukka Boot (Men)Was: $115.00Now: $68.9840% OFF
Deer Stags 'Seattle' Leather Chukka Boot (Men)
Deer Stags 'Seattle' Leather Chukka Boot (Men)
Timberland 'Newport Bay' Chukka Boot (Men)
Timberland 'Newport Bay' Chukka Boot (Men)
Timberland 'City Lite' Waterproof Chukka Boot (Men)
Timberland 'City Lite' Waterproof Chukka Boot (Men)
1901 'Grant' Plain Toe Boot (Men)
1901 'Grant' Plain Toe Boot (Men)
1901 'Grant' Plain Toe Boot (Men)Was: $115.00Now: $76.9033% OFF
Calvin Klein 'Nowles' Chukka Boot (Men)
Calvin Klein 'Nowles' Chukka Boot (Men)
Calvin Klein 'Nowles' Chukka Boot (Men)Was: $110.00Now: $76.9030% OFF
Clarks® Originals 'Desert' Boot (Men)
Clarks® Originals 'Desert' Boot (Men)
Clarks® Originals 'Desert' Boot (Men)Was: $130.00Now: $77.9040% OFF
Timberland Earthkeepers® 'Groveton' Chukka Sneaker (Men) (Online Only)
Timberland Earthkeepers® 'Groveton' Chukka Sneaker (Men) (Online Only)
Tretorn 'Bo' Rain Boot (Men)
Tretorn 'Bo' Rain Boot (Men)
Kenneth Cole Reaction 'News-Flash' Cap Toe Boot (Men)
Kenneth Cole Reaction 'News-Flash' Cap Toe Boot (Men)
Deer Stags 'Mean' Leather Chukka Boot (Men)
Deer Stags 'Mean' Leather Chukka Boot (Men)
Volcom 'Del Mesa' Suede Chukka Boot (Men)
Volcom 'Del Mesa' Suede Chukka Boot (Men)
Kenneth Cole Reaction 'Cap-S Off' Zip Boot (Men)
Kenneth Cole Reaction 'Cap-S Off' Zip Boot (Men)
Kenneth Cole Reaction 'Cap-S Off' Zip Boot (Men)Was: $140.00Now: $81.9540% OFF
Kenneth Cole Reaction 'Be A-Wear' Chelsea Boot (Men)
Kenneth Cole Reaction 'Be A-Wear' Chelsea Boot (Men)
Timberland 'Gorham Low' Waterproof Hiking Shoe (Men)
Timberland 'Gorham Low' Waterproof Hiking Shoe (Men)
Calvin Klein 'Damire' Double Monk Strap Shoe (Men)
Calvin Klein 'Damire' Double Monk Strap Shoe (Men)
Helly Hansen 'Berthed 3' Waterproof Leather Boot (Men)
Helly Hansen 'Berthed 3' Waterproof Leather Boot (Men)
Sperry 'Bahama Lug' Chukka Boot (Men)
Sperry 'Bahama Lug' Chukka Boot (Men)
Volcom 'Del Mesa' Water Resistant Chukka Boot (Men)
Volcom 'Del Mesa' Water Resistant Chukka Boot (Men)
Volcom 'Del Mesa' Chukka Boot (Men)
Volcom 'Del Mesa' Chukka Boot (Men)
Clarks® Originals 'Desert - Herschel Supply Co.' Chukka Boot (Men)
Clarks® Originals 'Desert -  Herschel Supply Co.' Chukka Boot (Men)
Kenneth Cole Reaction 'Nor-Th Bound' Plain Toe Boot (Men)
Kenneth Cole Reaction 'Nor-Th Bound' Plain Toe Boot (Men)
Clarks® 'Muckers' Waterproof Snow Boot (Men)
Clarks® 'Muckers' Waterproof Snow Boot (Men)
Clarks® 'Muckers' Waterproof Snow Boot (Men)Was: $150.00Now: $89.9040% OFF
Clarks® 'Bushwick Mid' Plain Toe Boot (Men)
Clarks® 'Bushwick Mid' Plain Toe Boot (Men)
Clarks® 'Bushwick Mid' Plain Toe Boot (Men)Was: $150.00Now: $89.9040% OFF
Calvin Klein Jeans 'Kai' Plain Toe Boot (Men)
Calvin Klein Jeans 'Kai' Plain Toe Boot (Men)
Price MatchedCalvin Klein Jeans 'Kai' Plain Toe Boot (Men)Was: $120.00Now: $89.9925% OFF
Helly Hansen 'The Forester' Water Repellent Leather Boot (Men)
Helly Hansen 'The Forester' Water Repellent Leather Boot (Men)
Kenneth Cole Reaction 'Thank Me Later' Boot (Men)
Kenneth Cole Reaction 'Thank Me Later' Boot (Men)
Base London 'Marauder' Chukka Boot (Men)
Base London 'Marauder' Chukka Boot (Men)
Base London 'Marauder' Chukka Boot (Men)Was: $158.00Now: $94.8040% OFF
Tommy Bahama 'Relaxology Collection - Riker' Chukka Boot (Men)
Tommy Bahama 'Relaxology Collection - Riker' Chukka Boot (Men)
Tretorn 'New Gunnar' Waterproof Rain Boot (Men)
Tretorn 'New Gunnar' Waterproof Rain Boot (Men)
Tretorn 'New Gunnar' Waterproof Rain Boot (Men)
Tretorn 'New Gunnar' Waterproof Rain Boot (Men)
Clarks® 'Faulkner Top' Zip Boot (Men)
Clarks® 'Faulkner Top' Zip Boot (Men)
Clarks® 'Faulkner Top' Zip Boot (Men)Was: $160.00Now: $95.9040% OFF
Tommy Bahama 'Relaxology Collection - Rivington' Moc Toe Chukka Boot (Men)
Tommy Bahama 'Relaxology Collection - Rivington' Moc Toe Chukka Boot (Men)
UGG® 'Lyle' Chukka Boot (Men)
UGG® 'Lyle' Chukka Boot (Men)
UGG® 'Lyle' Chukka Boot (Men)
UGG® 'Lyle' Chukka Boot (Men)
Kenneth Cole Reaction 'Crisis Ave-rted' Boot (Men)
Kenneth Cole Reaction 'Crisis Ave-rted' Boot (Men)
TOMS Chukka Boot (Men)
TOMS Chukka Boot (Men)
Kenneth Cole Reaction 'Hit Men' Cap Toe Boot
Kenneth Cole Reaction 'Hit Men' Cap Toe Boot
Kenneth Cole Reaction 'Hit Men' Cap Toe Boot
Kenneth Cole Reaction 'Hit Men' Cap Toe Boot
Eastland 'Porter 1955' Cap Toe Boot (Men)
Eastland 'Porter 1955' Cap Toe Boot (Men)
Eastland 'Oakwood 1955' Plain Toe Boot (Men)
Eastland 'Oakwood 1955' Plain Toe Boot (Men)
Eastland 'Oakwood 1955' Plain Toe Boot (Men)Was: $155.00Now: $99.9035% OFF
Andrew Marc 'Woodside' Chukka Boot (Men)
Andrew Marc 'Woodside' Chukka Boot (Men)
Andrew Marc 'Woodside' Chukka Boot (Men)Was: $200.00Now: $99.9050% OFF
ECCO 'Turn' Chukka Boot (Men)
ECCO 'Turn' Chukka Boot (Men)
Sandro Moscoloni 'Klarson' Chelsea Boot (Men)
Sandro Moscoloni 'Klarson' Chelsea Boot (Men)
Sandro Moscoloni 'Klarson' Chelsea Boot (Men)Was: $150.00Now: $99.9033% OFF
Robert Wayne 'Elbio' Plain Toe Boot (Men) (Nordstrom Exclusive)
Robert Wayne 'Elbio' Plain Toe Boot (Men) (Nordstrom Exclusive)
Ariat 'Spot Hog' Chelsea Boot (Men)
Ariat 'Spot Hog' Chelsea Boot (Men)
Kenneth Cole Reaction 'Steer the Wheel' Lace-Up Boot (Men)
Kenneth Cole Reaction 'Steer the Wheel' Lace-Up Boot (Men)
Kenneth Cole Reaction 'Select All' Plain Toe Boot (Men)
Kenneth Cole Reaction 'Select All' Plain Toe Boot (Men)
Kenneth Cole Reaction 'Wound Up' Zip Boot (Men)
Kenneth Cole Reaction 'Wound Up' Zip Boot (Men)
Kenneth Cole Reaction 'Wound Up' Zip Boot (Men)Was: $150.00Now: $100.5033% OFF
Base London 'Marauder' Chukka Boot (Men)
Base London 'Marauder' Chukka Boot (Men)
Base London 'Marauder' Chukka Boot (Men)Was: $158.00Now: $100.8035% OFF
Clarks® 'Dargo' Cap Toe Boot (Men)
Clarks® 'Dargo' Cap Toe Boot (Men)
Clarks® 'Dargo' Cap Toe Boot (Men)Was: $170.00Now: $101.9040% OFF
Eastland 'High Fidelity' Cap Toe Boot (Men)
Eastland 'High Fidelity' Cap Toe Boot (Men)
New MarkdownEastland 'High Fidelity' Cap Toe Boot (Men)Was: $120.00Now: $102.0215% OFF
UGG® 'Leighton' Chukka Boot (Men)
UGG® 'Leighton' Chukka Boot (Men)
UGG® 'Leighton' Chukka Boot (Men)Was: $159.95Now: $103.9035% OFF
UGG® 'Leighton' Chukka Boot (Men)
UGG® 'Leighton' Chukka Boot (Men)
Calvin Klein 'Tyson' Zip Boot (Men)
Calvin Klein 'Tyson' Zip Boot (Men)
Price MatchedCalvin Klein 'Tyson' Zip Boot (Men)Was: $140.00Now: $104.9025% OFF
Joe's 'Slick' Suede Chukka Boot (Men)
Joe's 'Slick' Suede Chukka Boot (Men)
Joe's 'Slick' Suede Chukka Boot (Men)Was: $175.00Now: $104.9640% OFF
Base London 'Brunel' Plain Toe Boot (Men)
Base London 'Brunel' Plain Toe Boot (Men)
Base London 'Brunel' Plain Toe Boot (Men)Was: $178.00Now: $106.8040% OFF
Base London 'Clapham' Cap Toe Boot (Men)
Base London 'Clapham' Cap Toe Boot (Men)
Base London 'Clapham' Cap Toe Boot (Men)Was: $178.00Now: $106.8040% OFF
UGG® 'Classic Mini - Tweed' Boot (Men)
UGG® 'Classic Mini - Tweed' Boot (Men)
UGG® 'Classic Mini - Tweed' Boot (Men)Was: $164.95Now: $106.9035% OFF
Kenneth Cole New York 'No Regrets' Chukka Boot (Men)
Kenneth Cole New York 'No Regrets' Chukka Boot (Men)
Calvin Klein 'Harding' Plain Toe Boot (Men)
Calvin Klein 'Harding' Plain Toe Boot (Men)
Calvin Klein 'Harding' Plain Toe Boot (Men)Was: $155.00Now: $108.5030% OFF
TOMS 'Cordova' Boot (Men)
TOMS 'Cordova' Boot (Men)
TOMS 'Cordova' Water Resistant Boot (Men)
TOMS 'Cordova' Water Resistant Boot (Men)
TOMS 'Cordova' Boot (Men)
TOMS 'Cordova' Boot (Men)
Clarks® 'Montacute Duke' Boot (Men)
Clarks® 'Montacute Duke' Boot (Men)
Price MatchedClarks® 'Montacute Duke' Boot (Men)Was: $140.00Now: $109.9020% OFF
ALDO 'Yossef' Cap Toe Boot (Men)
ALDO 'Yossef' Cap Toe Boot (Men)
ALDO 'Yossef' Cap Toe Boot (Men)Was: $185.00Now: $109.9040% OFF
UGG® 'Parkhurst' Cap Toe Boot (Men)
UGG® 'Parkhurst' Cap Toe Boot (Men)
Cole Haan 'Paul' Chukka Boot
Cole Haan 'Paul' Chukka Boot
John Varvatos Star USA 'Hipster' Chukka Boot (Men)
John Varvatos Star USA 'Hipster' Chukka Boot (Men)
Andrew Marc 'Woodside' Chukka Boot (Men)
Andrew Marc 'Woodside' Chukka Boot (Men)
Andrew Marc 'Woodside' Chukka Boot (Men)Was: $218.00Now: $109.9050% OFF

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