Available 24/7 at (800) 927-7671

Join Zappos Rewards and Get Expedited Shipping!*

My Cart

“chukka and Men Boots” we found 92 items!

Choose a
  • Product Type
to sort results
Show Filters
View More Like This Clarks - Newkirk Top
Clarks Newkirk Top $135.00 Rated: 5 stars!
View More Like This Kenneth Cole Reaction - Desert Sun
Kenneth Cole Reaction Desert Sun $79.99 Rated: 5 stars!
View More Like This Johnston & Murphy - Copeland Chukka
Johnston & Murphy Copeland Chukka $158.95 Rated: 4 stars!
View More Like This Johnston & Murphy - Copeland Chukka
Johnston & Murphy Copeland Chukka $158.95 Rated: 4 stars!

View More Like This Dr. Martens - Cabrillo
Dr. Martens Cabrillo $80.00 Rated: 5 stars!
View More Like This Kenneth Cole Reaction - Desert Sun
Kenneth Cole Reaction Desert Sun $79.99 $66.95 Rated: 5 stars!
View More Like This Steve Madden - Hacksaw
Steve Madden Hacksaw $90.00
View More Like This Johnston & Murphy - Copeland Chukka
Johnston & Murphy Copeland Chukka $158.95 Rated: 4 stars!

View More Like This Clarks - Franson Top
Clarks Franson Top $115.00 $104.99 Rated: 4 stars!
Steve Madden - Overring
Steve Madden Overring $80.00
NEW!
View More Like This Clarks - Wallabee Boot
Clarks Wallabee Boot $140.00 Rated: 5 stars!
View More Like This Deer Stags - Seattle
Deer Stags Seattle $80.00 $59.99 Rated: 4 stars!

View More Like This Born - Boulder
Born Boulder $105.00
NEW!
Steve Madden - Overring
Steve Madden Overring $80.00
NEW!
View More Like This Steve Madden - Hacksaw
Steve Madden Hacksaw $90.00
View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $110.00 $99.95 Rated: 5 stars!

View More Like This Steve Madden - Herrin
Steve Madden Herrin $90.00 $72.99
View More Like This Dunham - REVdash
Dunham REVdash $149.95 Rated: 4 stars!
View More Like This Steve Madden - Herrin
Steve Madden Herrin $90.00 $62.99
View More Like This Georgia Boot - Small Batch Chukka
Georgia Boot Small Batch Chukka $140.00

View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $80.00 Rated: 5 stars!
View More Like This Danner - Wolf Creek Chukka
Danner Wolf Creek Chukka $180.00 Rated: 5 stars!
View More Like This Clarks - Desert Trek
Clarks Desert Trek $140.00 Rated: 4 stars!
View More Like This Steve Madden - Hotshot
Steve Madden Hotshot $85.00 Rated: 4 stars!

View More Like This Clarks - Stratton Limit
Clarks Stratton Limit $135.00 Rated: 4 stars!
View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $110.00 $94.99 Rated: 5 stars!
View More Like This Steve Madden - Hacksaw
Steve Madden Hacksaw $90.00
View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $110.00 $98.99 Rated: 5 stars!

View More Like This Vivobarefoot - Gobi II M Leather
Vivobarefoot Gobi II M Leather $150.00 Rated: 4 stars!
View More Like This Red Wing Heritage - Work Chukka
Red Wing Heritage Work Chukka $260.00 Rated: 4 stars!
View More Like This Steve Madden - Hacksaw
Steve Madden Hacksaw $90.00
View More Like This ECCO - Turn GTX Boot
ECCO Turn GTX Boot $230.00 Rated: 5 stars!

View More Like This Clarks - Clarkdale Jean
Clarks Clarkdale Jean $170.00
View More Like This Deer Stags - Seattle
Deer Stags Seattle $80.00 $59.99 Rated: 4 stars!
View More Like This Blundstone - BL268
Blundstone BL268 $174.95 Rated: 4 stars!
View More Like This Clarks - Stratton Limit
Clarks Stratton Limit $135.00 Rated: 4 stars!

View More Like This Ted Baker - Torsdi 4
Ted Baker Torsdi 4 $220.00 $197.99
View More Like This Red Wing Heritage - Foreman Chukka
Red Wing Heritage Foreman Chukka $290.00 Rated: 5 stars!
View More Like This The North Face - Bridgeton Chukka
The North Face Bridgeton Chukka $160.00 Rated: 2 stars!
View More Like This Danner - Wolf Creek Chukka
Danner Wolf Creek Chukka $180.00 Rated: 5 stars!

View More Like This Naot Footwear - Pilot
Naot Footwear Pilot $199.95 Rated: 4 stars!
Red Wing Heritage - Weekender Chukka
Red Wing Heritage Weekender Chukka $230.00
View More Like This Red Wing Heritage - Work Chukka
Red Wing Heritage Work Chukka $260.00 Rated: 4 stars!
View More Like This Wolverine - Hensel
Wolverine Hensel $195.00 Rated: 5 stars!

View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $110.00 $99.95 Rated: 5 stars!
View More Like This Dr. Martens - Cabrillo
Dr. Martens Cabrillo $80.00 Rated: 5 stars!
View More Like This Steve Madden - Hotshot
Steve Madden Hotshot $85.00 Rated: 4 stars!
View More Like This Clarks - Clarkdale Bud
Clarks Clarkdale Bud $170.00

View More Like This Blundstone - BL278
Blundstone BL278 $174.95 Rated: 4 stars!
View More Like This Dr. Martens - Diego 7 Tie Lace To Toe Boot
Dr. Martens Diego 7 Tie Lace To Toe Boot $135.00 Rated: 5 stars!
View More Like This Massimo Matteo - 3-Eye Chukka
Massimo Matteo 3-Eye Chukka $169.00 Rated: 5 stars!
View More Like This Justin - WK275
Justin WK275 $119.95 Rated: 3 stars!

View More Like This Irish Setter - Borderland Chukka
Irish Setter Borderland Chukka $190.00 $169.95 Rated: 4 stars!
View More Like This Wolverine - Hensel
Wolverine Hensel $195.00 Rated: 5 stars!
View More Like This Naot Footwear - Pilot
Naot Footwear Pilot $200.00 Rated: 4 stars!
View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $110.00 $99.95 Rated: 5 stars!

View More Like This Bed Stu - Curtis
Bed Stu Curtis $155.00 Rated: 4 stars!
View More Like This Dunham - REVdash
Dunham REVdash $149.95 Rated: 4 stars!
View More Like This Rockport - Rugged Bucks Moc Boot Waterproof
Rockport Rugged Bucks Moc Boot Waterproof $119.95 Rated: 3 stars!
View More Like This Clarks - Clarkdale Bud
Clarks Clarkdale Bud $170.00

View More Like This Danner - Wolf Creek Chukka
Danner Wolf Creek Chukka $180.00 Rated: 5 stars!
View More Like This Caterpillar - Trey
Caterpillar Trey $110.00
View More Like This Steve Madden - Hotshot
Steve Madden Hotshot $85.00 $71.95 Rated: 4 stars!
View More Like This Trask - Arlington
Trask Arlington $275.00 Rated: 5 stars!

View More Like This Dockers - Tussock
Dockers Tussock $100.00 $69.95 Rated: 4 stars!
View More Like This Ted Baker - Azzlan
Ted Baker Azzlan $245.00 Rated: 5 stars!
View More Like This Roper - Performance 2-Eyelet Ankle Boot
Roper Performance 2-Eyelet Ankle Boot $120.00 Rated: 4 stars!
View More Like This Roper - Siped Outsole Performance Ankle Boot
Roper Siped Outsole Performance Ankle Boot $120.00 Rated: 5 stars!

View More Like This Sperry - Gold Crepe Chukka
Sperry Gold Crepe Chukka $220.00
View More Like This Ted Baker - Torsdi 4
Ted Baker Torsdi 4 $220.00
View More Like This Sperry - Gold Crepe Chukka
Sperry Gold Crepe Chukka $220.00
View More Like This Dr. Scholl's - Freewill - Original Collection
Dr. Scholl's Freewill - Original Collection $100.00 Rated: 5 stars!

View More Like This Steve Madden - Hacksaw
Steve Madden Hacksaw $90.00
View More Like This Clarks - Desert Trek
Clarks Desert Trek $140.00 Rated: 4 stars!
View More Like This Steve Madden - Hotshot
Steve Madden Hotshot $85.00 $71.95 Rated: 4 stars!
eleventy - Suede Chukka Boot
eleventy Suede Chukka Boot $475.00
LUXURY

View More Like This Justin - WK277
Justin WK277 $119.95
View More Like This Trask - Arlington
Trask Arlington $275.00 Rated: 5 stars!
View More Like This Fred Perry - Byron Mid Leather
Fred Perry Byron Mid Leather $125.00 Rated: 3 stars!
Chaco - Thompson Chukka
Chaco Thompson Chukka $135.00
NEW!

Chaco - Thompson Chukka
Chaco Thompson Chukka $135.00
NEW!
View More Like This Roper - Performance 2-Eyelet Ankle Boot
Roper Performance 2-Eyelet Ankle Boot $125.00 Rated: 4 stars!
Two24 by Ariat - Prescott
Two24 by Ariat Prescott $295.00
Two24 by Ariat - Prescott
Two24 by Ariat Prescott $295.00

View More Like This Dunham - REVdash
Dunham REVdash $149.95 Rated: 4 stars!
Ariat - Spitfire
Ariat Spitfire $89.95
NEW!
Ariat - Spitfire
Ariat Spitfire $89.95
NEW!
View More Like This Ted Baker - Torsdi 2
Ted Baker Torsdi 2 $220.00 Rated: 4 stars!

View More Like This Steve Madden - Hotshot
Steve Madden Hotshot $85.00 $59.99 Rated: 4 stars!
View More Like This Dr. Martens - 1919
Dr. Martens 1919 $145.00 Rated: 5 stars!
View More Like This Stacy Adams - Madison II - 65
Stacy Adams Madison II - 65 $180.00 $125.99 Rated: 4 stars!
View More Like This Dr. Scholl's - Freewill - Original Collection
Dr. Scholl's Freewill - Original Collection $100.00 Rated: 5 stars!

Thank You for Registering!

Now, don't miss out on the good stuff...