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“chukka and Men Boots” we found 112 items!

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View More Like This Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 $109.95 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 - Classic Break Chukka
Rockport Classic Break Chukka $119.95 Rated: 5 stars!
View More Like This Rockport - Rugged Bucks Moc Boot Waterproof
Rockport Rugged Bucks Moc Boot Waterproof $119.95 $89.95 Rated: 3 stars!

View More Like This Rockport - Total Motion Fusion Desert Boot
Rockport Total Motion Fusion Desert Boot $149.95 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 ECCO - Turn GTX Boot
ECCO Turn GTX Boot $230.00 Rated: 5 stars!
View More Like This Rockport - Total Motion Fusion Desert Boot
Rockport Total Motion Fusion Desert Boot $149.95 Rated: 5 stars!

View More Like This Merrell - Freewheel Mesh Chukka
Merrell Freewheel Mesh Chukka $100.00 Rated: 5 stars!
View More Like This Cole Haan - Zerogrand Stitchout Chukka
Cole Haan Zerogrand Stitchout Chukka $280.00 Rated: 5 stars!
View More Like This Wolverine - Francisco Chukka
Wolverine Francisco Chukka $180.00 $125.99 Rated: 5 stars!
View More Like This Merrell - Freewheel Mesh Chukka
Merrell Freewheel Mesh Chukka $100.00 Rated: 5 stars!

View More Like This Timberland - Groveton Leather and Fabric Chukka
Timberland Groveton Leather and Fabric Chukka $80.00 Rated: 5 stars!
View More Like This Rockport - Prestige Point Chukka
Rockport Prestige Point Chukka $174.95 Rated: 5 stars!
View More Like This Timberland - Carter Notch Waterproof Plain Toe Chukka
Timberland Carter Notch Waterproof Plain Toe Chukka $140.00 Rated: 4 stars!
View More Like This Oliberte - Adibo
Oliberte Adibo $120.00 Rated: 4 stars!

View More Like This Timberland - Westmore Leather Fabric Chukka
Timberland Westmore Leather Fabric Chukka $149.95
View More Like This Chaco - Montrose Chukka
Chaco Montrose Chukka $139.95 Rated: 5 stars!
View More Like This Rockport - Prestige Point Chukka
Rockport Prestige Point Chukka $174.95 Rated: 5 stars!
View More Like This Timberland - Carter Notch Waterproof Plain Toe Chukka
Timberland Carter Notch Waterproof Plain Toe Chukka $140.00 Rated: 4 stars!

View More Like This Sperry - Clipper Chukka
Sperry Clipper Chukka $120.00 Rated: 5 stars!
View More Like This Sperry - Dockyard Chukka
Sperry Dockyard Chukka $150.00 $104.99 Rated: 5 stars!
View More Like This SOREL - Madson Moc Toe
SOREL Madson Moc Toe $190.00 Rated: 5 stars!
View More Like This Wolverine - Cort Waterproof Leather Chukka
Wolverine Cort Waterproof Leather Chukka $160.00 Rated: 5 stars!

View More Like This Columbia - Sunvent Chukka
Columbia Sunvent Chukka $90.00
View More Like This Rockport - Prestige Point Chukka
Rockport Prestige Point Chukka $174.95 Rated: 5 stars!
View More Like This UGG - Leighton
UGG Leighton $159.95 Rated: 4 stars!
View More Like This Danner - Wolf Creek Chukka
Danner Wolf Creek Chukka $180.00 Rated: 5 stars!

View More Like This Timberland - Groveton Plain Toe Chukka Leather and Fabric
Timberland Groveton Plain Toe Chukka Leather and Fabric $90.00 Rated: 5 stars!
View More Like This UGG - Freamon Capra
UGG Freamon Capra $149.95 Rated: 3 stars!
View More Like This John Varvatos - Brooklyn Chukka
John Varvatos Brooklyn Chukka $228.00
View More Like This UGG - Neumel Gradient Perf
UGG Neumel Gradient Perf $149.95 $104.97 Rated: 5 stars!

View More Like This Timberland - Earthkeepers® Brook Park Chukka
Timberland Earthkeepers® Brook Park Chukka $110.00 Rated: 5 stars!
View More Like This Oliberte - Adibo
Oliberte Adibo $120.00 $95.99 Rated: 4 stars!
View More Like This Naot Footwear - Pilot - Hand Crafted
Naot Footwear Pilot - Hand Crafted $240.00
View More Like This BOSS Hugo Boss - Pariss Desb by HUGO
BOSS Hugo Boss Pariss Desb by HUGO $275.00 $192.99 Rated: 4 stars!

View More Like This Merrell - Brevard Chukka
Merrell Brevard Chukka $150.00 Rated: 2 stars!
View More Like This UGG - Larken Stripe Perf
UGG Larken Stripe Perf $169.95 Rated: 4 stars!
View More Like This Cycleur de Luxe - Lima
Cycleur de Luxe Lima $185.00 $147.99
View More Like This Wolverine - Cort Waterproof Leather Chukka
Wolverine Cort Waterproof Leather Chukka $160.00 Rated: 5 stars!

View More Like This Justin - WK277
Justin WK277 $135.00
View More Like This TOMS - Mateo Chukka Boot
TOMS Mateo Chukka Boot $98.00 Rated: 5 stars!
View More Like This Stacy Adams - Delaney Chukka Boot
Stacy Adams Delaney Chukka Boot $105.00 $74.99 Rated: 4 stars!
View More Like This Sperry - A/O Mini Lug Chukka
Sperry A/O Mini Lug Chukka $120.00 $84.99

View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $110.00 $99.95 Rated: 5 stars!
View More Like This UGG - Larken Stripe Perf
UGG Larken Stripe Perf $169.95 Rated: 4 stars!
View More Like This Sperry - Dockyard Chukka
Sperry Dockyard Chukka $150.00 $104.99 Rated: 5 stars!
View More Like This Timberland - Groveton Plain Toe Chukka Leather and Fabric
Timberland Groveton Plain Toe Chukka Leather and Fabric $90.00 Rated: 5 stars!

View More Like This Cole Haan - 2.Zerogrand Chukka
Cole Haan 2.Zerogrand Chukka $320.00
View More Like This SOREL - Madson Chukka
SOREL Madson Chukka $170.00 Rated: 4 stars!
NEW!
View More Like This Calvin Klein - Jae
Calvin Klein Jae $140.00 $97.99 Rated: 4 stars!
View More Like This Irish Setter - Borderland Chukka
Irish Setter Borderland Chukka $190.00 $169.95 Rated: 4 stars!

View More Like This SOREL - Madson Moc Toe
SOREL Madson Moc Toe $190.00 Rated: 5 stars!
View More Like This The North Face - Ballard EVO Chukka FG
The North Face Ballard EVO Chukka FG $110.00 $77.00 Rated: 3 stars!
View More Like This Caterpillar - Mitch
Caterpillar Mitch $90.00 Rated: 5 stars!
View More Like This Merrell - Freewheel Mesh Chukka
Merrell Freewheel Mesh Chukka $100.00 Rated: 5 stars!

View More Like This BOSS Hugo Boss - Pariss Desb by HUGO
BOSS Hugo Boss Pariss Desb by HUGO $275.00 $192.99 Rated: 4 stars!
View More Like This TOMS - Chukka Boot
TOMS Chukka Boot $98.00 Rated: 4 stars!
View More Like This Sperry - Sojourn Duck Chukka Boot
Sperry Sojourn Duck Chukka Boot $110.00 Rated: 4 stars!
View More Like This Wolverine - Ranger 6
Wolverine Ranger 6" Moc Toe $140.00

View More Like This Sebago - Vershire Chukka
Sebago Vershire Chukka $139.95
View More Like This SOREL - Ankeny™ Mid Hiker
SOREL Ankeny™ Mid Hiker $135.00 Rated: 4 stars!
View More Like This Caterpillar - Mitch
Caterpillar Mitch $90.00 Rated: 5 stars!
View More Like This Ariat - Exhibitor
Ariat Exhibitor $109.95

View More Like This Calvin Klein - Kenley
Calvin Klein Kenley $130.00
View More Like This Calvin Klein - Kenley
Calvin Klein Kenley $130.00
View More Like This Frye - James Lug Chukka Shearling
Frye James Lug Chukka Shearling $388.00 $310.40 Rated: 5 stars!
View More Like This Cole Haan - Zerogrand Stitchout Chukka
Cole Haan Zerogrand Stitchout Chukka $280.00 Rated: 5 stars!

View More Like This Jambu - Tavern
Jambu Tavern $189.00
View More Like This Jambu - Tavern
Jambu Tavern $189.00
View More Like This Jambu - Tavern
Jambu Tavern $189.00
View More Like This Trask - Arlington
Trask Arlington $275.00 $192.99 Rated: 5 stars!

View More Like This SOREL - Madson Chukka
SOREL Madson Chukka $170.00 Rated: 4 stars!
View More Like This Z Zegna - Chukka Grained Calf/Neoprene Boot
Z Zegna Chukka Grained Calf/Neoprene Boot $395.00
LUXURY
View More Like This Wolverine - Ranger 6
Wolverine Ranger 6" Moc Toe $135.00
View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $110.00 $99.95 Rated: 5 stars!

View More Like This Rockport - Jaxson Chukka
Rockport Jaxson Chukka $159.95
View More Like This UGG - Freamon Canvas
UGG Freamon Canvas $109.95
View More Like This UGG - Hendrickson Capra
UGG Hendrickson Capra $159.95
View More Like This Lacoste - Laccord Chukka 117 1 Cam
Lacoste Laccord Chukka 117 1 Cam $159.95 $112.99

View More Like This Hush Puppies - Waterproof Benson Rigby ICE+
Hush Puppies Waterproof Benson Rigby ICE+ $180.00 Rated: 2 stars!
View More Like This SOREL - Ankeny™ Mid Hiker
SOREL Ankeny™ Mid Hiker $135.00 Rated: 4 stars!
View More Like This UGG - Leighton Bomber
UGG Leighton Bomber $179.95 Rated: 4 stars!
View More Like This Caterpillar - Mitch
Caterpillar Mitch $90.00 Rated: 5 stars!

View More Like This Chippewa - 5' Modern Suburban Boot
Chippewa 5' Modern Suburban Boot $280.00 $210.99
View More Like This Cole Haan - 2.Zerogrand Chukka
Cole Haan 2.Zerogrand Chukka $320.00
View More Like This Calvin Klein - Kenley
Calvin Klein Kenley $130.00
View More Like This UGG - Neumel
UGG Neumel $129.95 Rated: 4 stars!

View More Like This Merrell - Brevard Chukka
Merrell Brevard Chukka $150.00 Rated: 2 stars!
View More Like This Timberland - Westmore Leather Fabric Chukka
Timberland Westmore Leather Fabric Chukka $149.95
View More Like This Wolverine - Ranger 6
Wolverine Ranger 6" Moc Toe $135.00
View More Like This UGG - Freamon Canvas
UGG Freamon Canvas $109.95

View More Like This UGG - Maksim
UGG Maksim $124.95 Rated: 5 stars!
UGG - Maksim
UGG Maksim $124.95 Rated: 5 stars!
View More Like This UGG - Hendrickson Capra
UGG Hendrickson Capra $159.95
Jeffery-West - Sylvian Day Dead
Jeffery-West Sylvian Day Dead $308.00
LUXURY

View More Like This UGG - Larken Stripe Perf
UGG Larken Stripe Perf $169.95 Rated: 4 stars!
View More Like This Chrome - Suede Chukka
Chrome Suede Chukka $120.00 $84.99
View More Like This UGG - Neumel
UGG Neumel $139.95 Rated: 4 stars!
View More Like This Base London - Morris
Base London Morris $140.00 $97.99