Skip Navigation
Shopping Bag [0]Checkout
  • There are currently no items in your Shopping Bag.

Buy online & pick up in store.
Main Content

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

Narrow by:
Sorel 'Conquest' Boot (Men)
Sorel 'Conquest' Boot (Men)
Eastland 'Stonington 1955' Boot
Eastland 'Stonington 1955' Boot
Ariat 'Mesteno' Boot (Men)
Ariat 'Mesteno' Boot (Men)
Ariat 'Heritage Roughstock' Boot (Online Only) (Men)
Ariat 'Heritage Roughstock' Boot (Online Only) (Men)
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
Base London 'Marauder' Chukka Boot (Men)
Base London 'Marauder' Chukka Boot (Men)
Base London 'Marauder' Chukka Boot (Men)Was: $158.00Now: $100.8035% OFF
BOGA 'Commuter' Chukka Boot (Men)
BOGA 'Commuter' Chukka Boot (Men)
New MarkdownBOGA 'Commuter' Chukka Boot (Men)Was: $398.00Now: $237.9040% OFF
BOGA 'Union' Cap Toe Boot (Men)
BOGA 'Union' Cap Toe Boot (Men)
New MarkdownBOGA 'Union' Cap Toe Boot (Men)Was: $425.00Now: $254.9040% OFF
BOGA 'Bossman' Wingtip Boot (Men)
BOGA 'Bossman' Wingtip Boot (Men)
New MarkdownBOGA 'Bossman' Wingtip Boot (Men)Was: $425.00Now: $254.9040% OFF
BOGA 'Union' Boot (Men)
BOGA 'Union' Boot (Men)
New MarkdownBOGA 'Union' Boot (Men)Was: $425.00Now: $254.9040% OFF
Joe's 'Aaron' Boot (Men)
Joe's 'Aaron' Boot (Men)
Joe's 'Aaron' Boot (Men)Was: $195.00Now: $117.0040% OFF
Joe's 'Tyler' Wingtip Boot (Men)®
Joe's 'Tyler' Wingtip Boot (Men)®
Joe's 'Tyler' Wingtip Boot (Men)®Was: $230.00Now: $138.0040% OFF
Trask 'Fallon' Wingtip Boot (Men)
Trask 'Fallon' Wingtip Boot (Men)
Trask 'Fallon' Wingtip Boot (Men)Was: $275.00Now: $206.0025% OFF
UGG® 'Lyle' Chukka Boot (Men)
UGG® 'Lyle' Chukka Boot (Men)
BOGA Double Monk Strap Boot (Men)
BOGA Double Monk Strap Boot (Men)
New MarkdownBOGA Double Monk Strap Boot (Men)Was: $425.00Now: $254.9040% OFF
Cole Haan 'ZerøGrand Sport Mid' Boot (Men)
Cole Haan 'ZerøGrand Sport Mid' Boot (Men)
Cole Haan 'ZerøGrand Sport Mid' Boot (Men)Was: $278.00Now: $166.8040% OFF
Ted Baker London 'Sealls' Wingtip Boot
Ted Baker London 'Sealls' Wingtip Boot
Ted Baker London 'Sealls' Wingtip BootWas: $270.00Now: $196.0025% OFF
Clarks® 'Faulkner Top' Zip Boot (Men)
Clarks® 'Faulkner Top' Zip Boot (Men)
Clarks® 'Faulkner Top' Zip Boot (Men)Was: $160.00Now: $95.9040% OFF
Joe's 'Cliff' Plain Toe Boot (Men)
Joe's 'Cliff' Plain Toe Boot (Men)
New MarkdownJoe's 'Cliff' Plain Toe Boot (Men)Was: $220.00Now: $143.0035% OFF
Joe's 'Dylan' Zip Boot (Men)
Joe's 'Dylan' Zip Boot (Men)
New MarkdownJoe's 'Dylan' Zip Boot (Men)Was: $210.00Now: $136.5035% OFF
Joe's 'Floyd' Plain Toe Boot (Men)
Joe's 'Floyd' Plain Toe Boot (Men)
New MarkdownJoe's 'Floyd' Plain Toe Boot (Men)Was: $240.00Now: $156.0035% OFF
Joe's 'Twist' Cap Toe Boot (Men)
Joe's 'Twist' Cap Toe Boot (Men)
New MarkdownJoe's 'Twist' Cap Toe Boot (Men)Was: $220.00Now: $143.0035% OFF
Trask 'Garfield' Moc Toe Boot (Men)
Trask 'Garfield' Moc Toe Boot (Men)
Trask 'Garfield' Moc Toe Boot (Men)Was: $325.00Now: $244.0025% OFF
Joe's 'Keven' Lace-Up Boot (Men)
Joe's 'Keven' Lace-Up Boot (Men)
New MarkdownJoe's 'Keven' Lace-Up Boot (Men)Was: $220.00Now: $143.0035% OFF
Timberland 'Gorham Low' Waterproof Hiking Shoe (Men)
Timberland 'Gorham Low' Waterproof Hiking Shoe (Men)
Mezlan 'Breman' Boot (Men)
Mezlan 'Breman' Boot (Men)
New MarkdownMezlan 'Breman' Boot (Men)Was: $395.00Now: $269.9030% OFF
Calvin Klein 'Walter' Chukka Boot (Men)
Calvin Klein 'Walter' Chukka Boot (Men)
Calvin Klein 'Walter' Chukka Boot (Men)Was: $175.00Now: $122.5030% OFF
Hunter 'Original' Waterproof Biker Boot (Men)
Hunter 'Original' Waterproof Biker Boot (Men)
Hunter 'Original' Waterproof Biker Boot (Men)Was: $250.00Now: $175.0030% OFF
Joe's 'Brody' Chelsea Boot (Men)
Joe's 'Brody' Chelsea Boot (Men)
Joe's 'Brody' Chelsea Boot (Men)Was: $220.00Now: $132.0040% OFF
Joe's 'Slops' Boot (Men)
Joe's 'Slops' Boot (Men)
Joe's 'Slops' Boot (Men)Was: $255.00Now: $153.0040% OFF
Kenneth Cole New York 'Fall Fever' Plain Toe Boot (Men)
Kenneth Cole New York 'Fall Fever' Plain Toe Boot (Men)
Andrew Marc 'Rutland' Boot (Men)
Andrew Marc 'Rutland' Boot (Men)
Andrew Marc 'Rutland' Boot (Men)Was: $378.00Now: $189.0050% OFF
Calvin Klein 'Harding' Plain Toe Boot (Men)
Calvin Klein 'Harding' Plain Toe Boot (Men)
Calvin Klein 'Harding' Plain Toe Boot (Men)Was: $155.00Now: $92.9840% OFF
Joe's 'Steve' Boot (Men)
Joe's 'Steve' Boot (Men)
Joe's 'Steve' Boot (Men)Was: $220.00Now: $132.0040% OFF
UGG® 'Alin' Twinsole® Chukka Boot (Men)
UGG® 'Alin' Twinsole® Chukka Boot (Men)
UGG® 'Alin' Twinsole® Chukka Boot (Men)Was: $149.95Now: $96.9035% OFF
Ted Baker London 'Challen' Chukka Boot (Men)
Ted Baker London 'Challen' Chukka Boot (Men)
Ted Baker London 'Challen' Chukka Boot (Men)Was: $240.00Now: $168.0030% OFF
Kenneth Cole New York 'Chill-Er' Plain Toe Boot (Men)
Kenneth Cole New York 'Chill-Er' Plain Toe Boot (Men)
Kenneth Cole New York 'Good Fella' Chukka (Men)
Kenneth Cole New York 'Good Fella' Chukka (Men)
Kenneth Cole New York 'Good Fella' Chukka (Men)Was: $175.00Now: $116.9033% OFF
Geox 'Fiesole - ABX' Amphibiox® Waterproof Boot (Men)
Geox 'Fiesole - ABX' Amphibiox® Waterproof Boot (Men)
Geox 'Yeti - ABX' Amphibiox® Waterproof Boot (Men)
Geox 'Yeti - ABX' Amphibiox® Waterproof Boot (Men)
Geox 'Fiesole - ABX' Amphibiox® Waterproof Boot (Men)
Geox 'Fiesole - ABX' Amphibiox® Waterproof Boot (Men)
Geox 'Rubbiano - ABX' Amphibiox® Waterproof Boot (Men)
Geox 'Rubbiano - ABX' Amphibiox® Waterproof Boot (Men)
Joe's 'Aaron' Boot (Men)
Joe's 'Aaron' Boot (Men)
New MarkdownJoe's 'Aaron' Boot (Men)Was: $195.00Now: $126.7535% OFF
Bacco Bucci 'Graz' Zip Boot (Men)
Bacco Bucci 'Graz' Zip Boot (Men)
Bacco Bucci 'Graz' Zip Boot (Men)Was: $295.00Now: $190.0035% 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
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
COACH 'Bryant' Jodhpur Boot (Men)
COACH 'Bryant' Jodhpur Boot (Men)
COACH 'Bryant' Jodhpur Boot (Men)Was: $375.00Now: $224.9040% OFF
Joe's 'Chuck' Chukka Boot (Men)
Joe's 'Chuck' Chukka Boot (Men)
Joe's 'Chuck' Chukka Boot (Men)Was: $185.00Now: $111.0040% OFF
Geox 'Mattias - ABX' Amphibiox® Waterproof Boot (Men)
Geox 'Mattias - ABX' Amphibiox® Waterproof Boot (Men)
Joe's 'Glenn' Boot (Men)
Joe's 'Glenn' Boot (Men)
New MarkdownJoe's 'Glenn' Boot (Men)Was: $220.00Now: $143.0035% OFF
Joe's 'Mitch' Plain Toe Boot (Men)
Joe's 'Mitch' Plain Toe Boot (Men)
Joe's 'Mitch' Plain Toe Boot (Men)Was: $230.00Now: $138.0040% OFF
Joe's 'Bobby' Chukka Boot (Men)
Joe's 'Bobby' Chukka Boot (Men)
Joe's 'Bobby' Chukka Boot (Men)Was: $195.00Now: $126.7535% OFF
Donald J Pliner 'Shale' Chelsea Boot (Men)
Donald J Pliner 'Shale' Chelsea Boot (Men)
Donald J Pliner 'Shale' Chelsea Boot (Men)Was: $375.00Now: $239.9035% OFF
Kenneth Cole New York 'In-Stead' Chukka Boot (Men)
Kenneth Cole New York 'In-Stead' Chukka Boot (Men)
Andrew Marc 'Norwood' Cap Toe Boot (Men)
Andrew Marc 'Norwood' Cap Toe Boot (Men)
Andrew Marc 'Norwood' Cap Toe Boot (Men)Was: $248.00Now: $148.8040% OFF
Calvin Klein 'Nowles' Chukka Boot (Men)
Calvin Klein 'Nowles' Chukka Boot (Men)
Calvin Klein 'Nowles' Chukka Boot (Men)Was: $110.00Now: $65.9840% OFF
Geox 'Brayden - ABX' Amphibiox® Waterproof Oxford (Men)
Geox 'Brayden - ABX' Amphibiox® Waterproof Oxford (Men)
Calvin Klein 'Damire' Double Monk Strap Shoe (Men)
Calvin Klein 'Damire' Double Monk Strap Shoe (Men)
Andrew Marc 'Midwood' Plain Toe Boot (Men)
Andrew Marc 'Midwood' Plain Toe Boot (Men)
Andrew Marc 'Midwood' Plain Toe Boot (Men)Was: $328.00Now: $180.4045% OFF
Kenneth Cole New York 'No Regrets' Chukka Boot (Men)
Kenneth Cole New York 'No Regrets' Chukka Boot (Men)
Mezlan 'Breman' Boot (Men)
Mezlan 'Breman' Boot (Men)
Mezlan 'Breman' Boot (Men)Was: $450.00Now: $269.9040% OFF
Kenneth Cole Reaction 'News-Flash' Cap Toe Boot (Men)
Kenneth Cole Reaction 'News-Flash' Cap Toe Boot (Men)
Kenneth Cole Reaction 'Nor-Th Bound' Plain Toe Boot (Men)
Kenneth Cole Reaction 'Nor-Th Bound' Plain Toe 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
Frye 'Jack' Double Monk Strap Chukka Boot (Men)
Frye 'Jack' Double Monk Strap Chukka Boot (Men)
New MarkdownFrye 'Jack' Double Monk Strap Chukka Boot (Men)Was: $348.00Now: $260.9925% OFF
To Boot New York 'Layton' Chukka Boot Sneaker (Men)
To Boot New York 'Layton' Chukka Boot Sneaker (Men)
John Varvatos Collection 'Norvegian' Plain Toe Boot (Men)
John Varvatos Collection 'Norvegian' Plain Toe 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
Kenneth Cole New York 'Click Here' Wingtip Zip Boot (Men)
Kenneth Cole New York 'Click Here' Wingtip Zip Boot (Men)
Bacco Bucci 'Dianmo' Plain Toe Boot (Men)
Bacco Bucci 'Dianmo' Plain Toe Boot (Men)
Bacco Bucci 'Dianmo' Plain Toe Boot (Men)Was: $295.00Now: $206.5030% OFF
Blackstone 'AM 19' Zip Boot (Men)
Blackstone 'AM 19' Zip Boot (Men)
Blackstone 'AM 19' Zip Boot (Men)Was: $269.00Now: $159.9640% OFF
Kenneth Cole New York 'Pass By' Plain Toe Boot (Men)
Kenneth Cole New York 'Pass By' Plain Toe Boot (Men)
Ted Baker London 'Decola' Zip Boot (Men)
Ted Baker London 'Decola' Zip Boot (Men)
Ted Baker London 'Decola' Zip Boot (Men)Was: $330.00Now: $197.9040% OFF
Tommy Bahama 'Edisto' Boot (Men)
Tommy Bahama 'Edisto' Boot (Men)
Tommy Bahama 'Edisto' Boot (Men)Was: $198.00Now: $117.9640% OFF
John Varvatos Star USA 'Strummer' Wingtip Boot (Men)
John Varvatos Star USA 'Strummer' Wingtip Boot (Men)
Kenneth Cole Reaction 'Be A-Wear' Chelsea Boot (Men)
Kenneth Cole Reaction 'Be A-Wear' Chelsea Boot (Men)
Eastland 'Silverado 1955' Leather Moc Toe Boot (Men)
Eastland 'Silverado 1955' Leather Moc Toe Boot (Men)
Andrew Marc 'Dorchester' Suede Chukka Boot (Men)
Andrew Marc 'Dorchester' Suede Chukka Boot (Men)
Andrew Marc 'Dorchester' Suede Chukka Boot (Men)Was: $198.00Now: $117.9040% OFF
Mezlan 'Balestra' Shearling Boot (Men)
Mezlan 'Balestra' Shearling Boot (Men)
Mezlan 'Balestra' Shearling Boot (Men)Was: $425.00Now: $297.5030% OFF
Tommy Bahama 'Relaxology Collection - Rivington' Moc Toe Chukka Boot (Men)
Tommy Bahama 'Relaxology Collection - Rivington' Moc Toe Chukka Boot (Men)
Timberland 'Coulter Collection' Leather Pull-On Boot (Men)
Timberland 'Coulter Collection' Leather Pull-On Boot (Men)
Trask 'Charlo' Moc Toe Boot (Men)
Trask 'Charlo' Moc Toe Boot (Men)
Trask 'Charlo' Moc Toe Boot (Men)Was: $475.00Now: $355.9025% OFF
Trask 'Buckhorn' Leather Chukka Boot (Men)
Trask 'Buckhorn' Leather Chukka Boot (Men)
Trask 'Buckhorn' Leather Chukka Boot (Men)Was: $475.00Now: $355.9025% OFF
Sandro Moscoloni 'Klarson' Chelsea Boot (Men)
Sandro Moscoloni 'Klarson' Chelsea Boot (Men)
Sandro Moscoloni 'Klarson' Chelsea Boot (Men)Was: $150.00Now: $99.9033% OFF
Wolverine '1000 Mile - Rowan' Boot (Online Only)
Wolverine '1000 Mile - Rowan' Boot (Online Only)
Andrew Marc 'Forest' Plain Toe Boot (Men)
Andrew Marc 'Forest' Plain Toe Boot (Men)
Andrew Marc 'Forest' Plain Toe Boot (Men)Was: $248.00Now: $148.8040% OFF
Bed Stu 'Revolution' Boot (Men)
Bed Stu 'Revolution' Boot (Men)

No items match all your filter selections.

Clear all to see unfiltered results.