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“chukka and Men Boots” we found 154 items!

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View More Like This Ariat - Exhibitor
Ariat Exhibitor $109.95
View More Like This Ariat - Exhibitor
Ariat Exhibitor $109.95
View More Like This Base London - Morris
Base London Morris $140.00 $97.99
View More Like This Ben Sherman - Antonio Lug
Ben Sherman Antonio Lug $135.00 $94.99 Rated: 3 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 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 Calvin Klein - Jae
Calvin Klein Jae $140.00 $97.99 Rated: 4 stars!
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 Calvin Klein - Kenley
Calvin Klein Kenley $130.00
View More Like This Caterpillar - Allay
Caterpillar Allay $110.00
View More Like This Caterpillar - Mitch
Caterpillar Mitch $90.00 Rated: 5 stars!

View More Like This Caterpillar - Mitch
Caterpillar Mitch $90.00 Rated: 5 stars!
View More Like This Caterpillar - Mitch
Caterpillar Mitch $90.00 Rated: 5 stars!
View More Like This Chaco - Montrose Chukka
Chaco Montrose Chukka $139.95 Rated: 5 stars!
View More Like This Chaco - Montrose Chukka
Chaco Montrose Chukka $139.95 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 Chrome - Suede Chukka
Chrome Suede Chukka $120.00 $84.99
View More Like This Clarks - Newkirk Top
Clarks Newkirk Top $135.00 Rated: 5 stars!
View More Like This Cole Haan - 2.Zerogrand Chukka
Cole Haan 2.Zerogrand Chukka $320.00

View More Like This Cole Haan - 2.Zerogrand Chukka
Cole Haan 2.Zerogrand Chukka $320.00
View More Like This Cole Haan - Zerogrand Stitchout Chukka
Cole Haan Zerogrand Stitchout Chukka $280.00 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 Columbia - Sunvent Chukka
Columbia Sunvent Chukka $90.00

View More Like This Columbia - Sunvent Chukka
Columbia Sunvent Chukka $90.00
View More Like This Cycleur de Luxe - Lima
Cycleur de Luxe Lima $185.00 $147.99
View More Like This Danner - Wolf Creek Chukka
Danner Wolf Creek Chukka $180.00 Rated: 5 stars!
View More Like This Danner - Wolf Creek Chukka
Danner Wolf Creek Chukka $180.00 Rated: 5 stars!

View More Like This Danner - Wolf Creek Chukka
Danner Wolf Creek Chukka $180.00 Rated: 5 stars!
View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $80.00 Rated: 5 stars!
NEW!
View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $110.00 $99.95 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 Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $110.00 $99.95 Rated: 5 stars!
View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $110.00 Rated: 5 stars!
View More Like This ECCO - Turn GTX Boot
ECCO Turn GTX Boot $230.00 Rated: 5 stars!
View More Like This El Naturalista - Yugen NG21
El Naturalista Yugen NG21 $159.90 $127.99 Rated: 4 stars!

View More Like This El Naturalista - Yugen NG21
El Naturalista Yugen NG21 $159.90 Rated: 4 stars!
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 Harley-Davidson - Candler
Harley-Davidson Candler $150.00
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 Hush Puppies - Waterproof Benson Rigby ICE+
Hush Puppies Waterproof Benson Rigby ICE+ $180.00 Rated: 2 stars!
View More Like This Irish Setter - Borderland Chukka
Irish Setter Borderland Chukka $190.00 $169.95 Rated: 4 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 Jeffery-West - Laser Chukka
Jeffery-West Laser Chukka $275.00
LUXURY
Jeffery-West - Sylvian Day Dead
Jeffery-West Sylvian Day Dead $308.00
LUXURY
View More Like This John Varvatos - Brooklyn Chukka
John Varvatos Brooklyn Chukka $228.00

View More Like This Josef Seibel - Oscar 11
Josef Seibel Oscar 11 $185.00 Rated: 5 stars!
View More Like This Josef Seibel - Oscar 11
Josef Seibel Oscar 11 $185.00 Rated: 5 stars!
View More Like This Josef Seibel - Willow 24
Josef Seibel Willow 24 $185.00 Rated: 4 stars!
View More Like This Justin - 235
Justin 235 $109.95 Rated: 5 stars!

View More Like This Justin - WK275
Justin WK275 $135.00 Rated: 3 stars!
View More Like This Justin - WK277
Justin WK277 $135.00
View More Like This Lacoste - Laccord Chukka 117 1 Cam
Lacoste Laccord Chukka 117 1 Cam $159.95 $112.99
Lacoste - Laccord Chukka 217 1
Lacoste Laccord Chukka 217 1 $159.95
NEW!

Lacoste - Laccord Chukka 217 1
Lacoste Laccord Chukka 217 1 $159.95
NEW!
View More Like This Merrell - Brevard Chukka
Merrell Brevard Chukka $150.00 Rated: 2 stars!
View More Like This Merrell - Brevard Chukka
Merrell Brevard Chukka $150.00 Rated: 2 stars!
View More Like This Merrell - Brevard Chukka
Merrell Brevard Chukka $150.00 Rated: 2 stars!

View More Like This Merrell - Freewheel Mesh Chukka
Merrell Freewheel Mesh Chukka $100.00 Rated: 5 stars!
View More Like This Merrell - Freewheel Mesh Chukka
Merrell Freewheel Mesh Chukka $100.00 Rated: 5 stars!
View More Like This Merrell - Freewheel Mesh Chukka
Merrell Freewheel Mesh Chukka $100.00 Rated: 5 stars!
View More Like This Naot Footwear - Pilot - Hand Crafted
Naot Footwear Pilot - Hand Crafted $240.00

View More Like This Oliberte - Adibo
Oliberte Adibo $120.00 $95.99 Rated: 4 stars!
View More Like This Oliberte - Adibo
Oliberte Adibo $120.00 Rated: 4 stars!
View More Like This Oliberte - Adibo
Oliberte Adibo $120.00 $95.99 Rated: 4 stars!
View More Like This OluKai - Pahoa
OluKai Pahoa $200.00 Rated: 5 stars!

View More Like This OluKai - Pahoa
OluKai Pahoa $200.00 Rated: 5 stars!
View More Like This OluKai - Pahoa
OluKai Pahoa $200.00 Rated: 5 stars!
View More Like This Rieker - F1310
Rieker F1310 $150.00
View More Like This Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 $109.95 Rated: 5 stars!

View More Like This Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 Rated: 5 stars!
View More Like This Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 $109.95 Rated: 5 stars!
View More Like This Rockport - Jaxson Chukka
Rockport Jaxson Chukka $159.95
View More Like This Rockport - Prestige Point Chukka
Rockport Prestige Point Chukka $174.95 Rated: 5 stars!

View More Like This Rockport - Prestige Point Chukka
Rockport Prestige Point Chukka $174.95 Rated: 5 stars!
View More Like This Rockport - Prestige Point Chukka
Rockport Prestige Point Chukka $174.95 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 Rockport - Total Motion Fusion Desert Boot
Rockport Total Motion Fusion Desert Boot $149.95 Rated: 5 stars!
View More Like This Sebago - Turner Chukka Waterproof
Sebago Turner Chukka Waterproof $139.95 Rated: 3 stars!
View More Like This Sebago - Turner Chukka Waterproof
Sebago Turner Chukka Waterproof $139.95 Rated: 3 stars!
View More Like This Sebago - Vershire Chukka
Sebago Vershire Chukka $139.95

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 SOREL - Ankeny™ Mid Hiker
SOREL Ankeny™ Mid Hiker $135.00 Rated: 4 stars!
View More Like This SOREL - Madson Chukka
SOREL Madson Chukka $170.00 Rated: 4 stars!

View More Like This SOREL - Madson Chukka
SOREL Madson Chukka $170.00 Rated: 4 stars!
View More Like This SOREL - Madson Chukka
SOREL Madson Chukka $170.00 Rated: 4 stars!
NEW!
View More Like This SOREL - Madson Chukka
SOREL Madson Chukka $170.00 Rated: 4 stars!
View More Like This SOREL - Madson Moc Toe
SOREL Madson Moc Toe $190.00 Rated: 5 stars!

View More Like This SOREL - Madson Moc Toe
SOREL Madson Moc Toe $190.00 Rated: 5 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 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 Sperry - Dockyard Chukka
Sperry Dockyard Chukka $150.00 $104.99 Rated: 5 stars!
View More Like This Sperry - Sojourn Duck Chukka Boot
Sperry Sojourn Duck Chukka Boot $110.00 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 Sperry - Sojourn Duck Chukka Boot
Sperry Sojourn Duck Chukka Boot $110.00 Rated: 4 stars!