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“chukka and Men Boots” we found 508 items!

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Caterpillar - Trey
Caterpillar Trey $110.00
NEW!
VIONIC - Chase
VIONIC Chase $159.95
NEW!
VIONIC - Chase
VIONIC Chase $159.95
NEW!
Robert Clergerie - Beezeena Boot
Robert Clergerie Beezeena Boot $575.00
LUXURY

John Varvatos - Brooklyn Chukka
John Varvatos Brooklyn Chukka $228.00
NEW!
John Varvatos - Brooklyn Chukka
John Varvatos Brooklyn Chukka $228.00
NEW!
Red Wing Heritage - Weekender Chukka
Red Wing Heritage Weekender Chukka $230.00
NEW!
John Varvatos - Brooklyn Chukka
John Varvatos Brooklyn Chukka $228.00
NEW!

Salvatore Ferragamo - Dufur Ankle Boot
Salvatore Ferragamo Dufur Ankle Boot $660.00
LUXURY
Cole Haan - Original Grand Chukka
Cole Haan Original Grand Chukka $180.00 Rated: 5 stars!
NEW!
Steve Madden - Herrin
Steve Madden Herrin $90.00
NEW!
Born - Harrison
Born Harrison $120.00 $110.00 Rated: 4 stars!
NEW!

Bed Stu - Hoover
Bed Stu Hoover $175.00 Rated: 4 stars!
NEW!
Steve Madden - Herrin
Steve Madden Herrin $90.00
NEW!
Cole Haan - Original Grand Chukka
Cole Haan Original Grand Chukka $180.00 Rated: 5 stars!
NEW!
Reef - Voyage Low
Reef Voyage Low $115.00
NEW!

Reef - Voyage Low
Reef Voyage Low $115.00
NEW!
Reef - Voyage Boot
Reef Voyage Boot $130.00
NEW!
Reef - Voyage Boot
Reef Voyage Boot $130.00
NEW!
Reef - Voyage Boot LE
Reef Voyage Boot LE $145.00
NEW!

Reef - Voyage Boot LE
Reef Voyage Boot LE $145.00
NEW!
Cole Haan - Original Grand Chukka
Cole Haan Original Grand Chukka $180.00 Rated: 5 stars!
NEW!
Mezlan - Adra
Mezlan Adra $395.00
NEW!
SOREL - Madson Chukka Waterproof
SOREL Madson Chukka Waterproof $170.00
NEW!

View More Like This SKECHERS - Mariner
SKECHERS Mariner $70.00 $49.99 Rated: 5 stars!
View More Like This Nunn Bush - Galloway Plain Toe Chukka Boot
Nunn Bush Galloway Plain Toe Chukka Boot $85.00 $68.00 Rated: 5 stars!
View More Like This Clarks - Desert Boot
Clarks Desert Boot $130.00 Rated: 5 stars!
View More Like This Clarks - Desert Boot
Clarks Desert Boot $130.00 Rated: 5 stars!

View More Like This Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 $109.95 Rated: 5 stars!
View More Like This Clarks - Desert Boot
Clarks Desert Boot $130.00 Rated: 5 stars!
View More Like This Deer Stags - Seattle
Deer Stags Seattle $80.00 $59.99 Rated: 4 stars!
View More Like This Clarks - Franson Top
Clarks Franson Top $115.00 $80.99 Rated: 5 stars!

View More Like This Deer Stags - Seattle
Deer Stags Seattle $80.00 $59.99 Rated: 4 stars!
View More Like This Steve Madden - Harken
Steve Madden Harken $85.00 Rated: 4 stars!
View More Like This Vans - Desert Chukka
Vans Desert Chukka $80.00 $55.99 Rated: 5 stars!
View More Like This Steve Madden - Harken
Steve Madden Harken $85.00 Rated: 4 stars!

View More Like This Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 $109.95 Rated: 5 stars!
View More Like This Cole Haan - GrandPro Chukka
Cole Haan GrandPro Chukka $150.00 $104.99 Rated: 5 stars!
View More Like This Clarks - Desert Boot
Clarks Desert Boot $130.00 $90.99 Rated: 5 stars!
View More Like This Timberland - Earthkeepers® Brook Park Chukka
Timberland Earthkeepers® Brook Park Chukka $110.00 $99.99 Rated: 5 stars!

View More Like This TOMS - Mateo Chukka Boot
TOMS Mateo Chukka Boot $98.00 $82.95 Rated: 5 stars!
View More Like This Nunn Bush - Galloway Plain Toe Chukka Boot
Nunn Bush Galloway Plain Toe Chukka Boot $80.00 $64.00 Rated: 5 stars!
View More Like This Rockport - Rugged Bucks Waterproof Boot
Rockport Rugged Bucks Waterproof Boot $119.95 $109.95 Rated: 4 stars!
View More Like This Clarks - Franson Top
Clarks Franson Top $115.00 $80.99 Rated: 5 stars!

View More Like This Dr. Martens - Cabrillo
Dr. Martens Cabrillo $80.00 Rated: 5 stars!
View More Like This Cole Haan - Barron Chukka
Cole Haan Barron Chukka $200.00 $129.90 Rated: 5 stars!
View More Like This Giorgio Brutini - Arlo
Giorgio Brutini Arlo $90.00 $62.99 Rated: 4 stars!
View More Like This Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 $99.95 Rated: 5 stars!

View More Like This Rockport - Ledge Hill 2 Chukka Boot
Rockport Ledge Hill 2 Chukka Boot $149.95 Rated: 4 stars!
View More Like This Rockport - Prestige Point Chukka
Rockport Prestige Point Chukka $174.95 $122.99 Rated: 5 stars!
View More Like This Nunn Bush - Galloway Plain Toe Chukka Boot
Nunn Bush Galloway Plain Toe Chukka Boot $80.00 $64.00 Rated: 5 stars!
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 ECCO - Kenton Plain Toe Boot
ECCO Kenton Plain Toe Boot $220.00 $154.99 Rated: 4 stars!
View More Like This Cole Haan - Zerogrand Stitchout Chukka
Cole Haan Zerogrand Stitchout Chukka $280.00 Rated: 5 stars!
View More Like This ECCO - Turn GTX Boot
ECCO Turn GTX Boot $230.00 $149.90 Rated: 5 stars!

View More Like This Johnston & Murphy - Copeland Chukka
Johnston & Murphy Copeland Chukka $154.95 Rated: 4 stars!
View More Like This Clarks - Desert Boot
Clarks Desert Boot $130.00 Rated: 5 stars!
View More Like This Johnston & Murphy - Copeland Chukka
Johnston & Murphy Copeland Chukka $154.95 Rated: 4 stars!
View More Like This Rockport - Dressports Luxe Waterproof Chukka
Rockport Dressports Luxe Waterproof Chukka $169.95 Rated: 5 stars!

View More Like This TOMS - Mateo Chukka Boot
TOMS Mateo Chukka Boot $98.00 Rated: 5 stars!
View More Like This Rockport - Essential Details Waterproof Dress Chukka
Rockport Essential Details Waterproof Dress Chukka $109.95 Rated: 4 stars!
View More Like This Vans - Desert Chukka
Vans Desert Chukka $105.00 Rated: 5 stars!
View More Like This Rockport - Dressports Business Chukka
Rockport Dressports Business Chukka $134.95 $129.95 Rated: 5 stars!

View More Like This Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 Rated: 5 stars!
View More Like This Deer Stags - Seattle
Deer Stags Seattle $80.00 $59.99 Rated: 4 stars!
View More Like This Cole Haan - Adams Chukka
Cole Haan Adams Chukka $180.00 $125.99
View More Like This Cole Haan - Barron Chukka
Cole Haan Barron Chukka $200.00 $129.90 Rated: 5 stars!

View More Like This UGG - Leighton
UGG Leighton $159.95 Rated: 4 stars!
UGG - Leighton Waterproof
UGG Leighton Waterproof $169.95
View More Like This Clarks - Desert Boot
Clarks Desert Boot $130.00 Rated: 5 stars!
View More Like This Clarks - Desert Boot
Clarks Desert Boot $140.00 $97.99 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 Dunham - Johnson Chukka
Dunham Johnson Chukka $149.95 Rated: 4 stars!
View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $110.00 $99.95 Rated: 5 stars!
Kenneth Cole Reaction - Desert Sun
Kenneth Cole Reaction Desert Sun $98.00 $64.99 Rated: 5 stars!

Steve Madden - Hacksaw
Steve Madden Hacksaw $90.00
View More Like This SOREL - Madson Moc Toe
SOREL Madson Moc Toe $190.00 $133.00 Rated: 5 stars!
View More Like This TOMS - Mateo Chukka Boot
TOMS Mateo Chukka Boot $98.00 $69.99 Rated: 5 stars!
View More Like This Merrell - Freewheel Mesh Chukka
Merrell Freewheel Mesh Chukka $100.00 $69.99 Rated: 4 stars!

View More Like This Clarks - Stratton Limit
Clarks Stratton Limit $135.00 Rated: 4 stars!
View More Like This Nunn Bush - Galloway Plain Toe Chukka Boot
Nunn Bush Galloway Plain Toe Chukka Boot $80.00 $64.00 Rated: 5 stars!
View More Like This Wolverine - Francisco Chukka
Wolverine Francisco Chukka $180.00 $125.99 Rated: 4 stars!
View More Like This Dr. Martens - Mayport 2-Eye Desert Boot
Dr. Martens Mayport 2-Eye Desert Boot $70.00 Rated: 5 stars!

View More Like This Cole Haan - Barron Chukka
Cole Haan Barron Chukka $200.00 $139.99 Rated: 5 stars!
View More Like This Steve Madden - Hestonn
Steve Madden Hestonn $85.00 $76.50 Rated: 4 stars!
View More Like This Steve Madden - Hotshot
Steve Madden Hotshot $85.00 $59.99 Rated: 4 stars!
View More Like This Danner - Wolf Creek Chukka
Danner Wolf Creek Chukka $180.00 Rated: 5 stars!

View More Like This Columbia - Sunvent Chukka
Columbia Sunvent Chukka $90.00
View More Like This Dunham - REVdash
Dunham REVdash $149.95 Rated: 4 stars!
View More Like This ECCO - Kenton Plain Toe Boot
ECCO Kenton Plain Toe Boot $220.00 $154.99 Rated: 4 stars!
ECCO - Kenton Plain Toe Boot
ECCO Kenton Plain Toe Boot $220.00 Rated: 4 stars!

View More Like This UGG - Leighton
UGG Leighton $159.95 $107.17 Rated: 4 stars!
View More Like This Merrell - Freewheel Mesh Chukka
Merrell Freewheel Mesh Chukka $100.00 Rated: 4 stars!
View More Like This UGG - Larken Stripe Perf
UGG Larken Stripe Perf $169.95 $113.87 Rated: 5 stars!
View More Like This Dr. Martens - Cabrillo
Dr. Martens Cabrillo $80.00 Rated: 5 stars!

View More Like This SOREL - Madson Chukka
SOREL Madson Chukka $119.00 Rated: 4 stars!
View More Like This Frye - Phillip Chukka
Frye Phillip Chukka $298.00 $209.99 Rated: 5 stars!
View More Like This Clarks - Broyd Mid
Clarks Broyd Mid $140.00 Rated: 5 stars!
View More Like This Clarks - Desert Boot
Clarks Desert Boot $140.00 $97.99 Rated: 5 stars!

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