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“chukka and Men Boots” we found 161 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 ECCO - Turn GTX Boot
ECCO Turn GTX Boot $230.00 $149.90 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 TOMS - Mateo Chukka Boot
TOMS Mateo Chukka Boot $98.00 $82.95 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 Rockport - Classic Break Chukka
Rockport Classic Break Chukka $119.95 $99.95 Rated: 5 stars!
View More Like This SOREL - Madson Moc Toe
SOREL Madson Moc Toe $190.00 $133.00 Rated: 5 stars!
View More Like This Rockport - Prestige Point Chukka
Rockport Prestige Point Chukka $174.95 $122.99 Rated: 5 stars!

View More Like This Merrell - Freewheel Mesh Chukka
Merrell Freewheel Mesh Chukka $100.00 $69.99 Rated: 4 stars!
UGG - Leighton Waterproof
UGG Leighton Waterproof $169.95
View More Like This Wolverine - Cort Waterproof Leather Chukka
Wolverine Cort Waterproof Leather Chukka $160.00 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 UGG - Leighton
UGG Leighton $159.95 $107.17 Rated: 4 stars!
View More Like This SOREL - Madson Moc Toe
SOREL Madson Moc Toe $133.00 Rated: 5 stars!
Rockport - Wynstin Chukka
Rockport Wynstin Chukka $119.95
View More Like This Cole Haan - Zerogrand Stitchout Chukka
Cole Haan Zerogrand Stitchout Chukka $280.00 Rated: 5 stars!

View More Like This Timberland - Groveton Leather and Fabric Chukka
Timberland Groveton Leather and Fabric Chukka $80.00 Rated: 5 stars!
Caterpillar - Trey
Caterpillar Trey $110.00
NEW!
View More Like This Clarks - Newkirk Top
Clarks Newkirk Top $135.00 Rated: 5 stars!
SOREL - Madson Chukka Waterproof
SOREL Madson Chukka Waterproof $170.00

View More Like This Danner - Wolf Creek Chukka
Danner Wolf Creek Chukka $180.00 Rated: 5 stars!
View More Like This SOREL - Madson Chukka
SOREL Madson Chukka $170.00 $119.00 Rated: 4 stars!
Georgia Boot - Small Batch Chukka
Georgia Boot Small Batch Chukka $140.00
View More Like This TOMS - Mateo Chukka Boot
TOMS Mateo Chukka Boot $98.00 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 SOREL - Madson Chukka
SOREL Madson Chukka $119.00 Rated: 4 stars!
View More Like This Wolverine - Francisco Chukka
Wolverine Francisco Chukka $180.00 $125.99 Rated: 4 stars!
View More Like This SOREL - Ankeny™ Mid Hiker
SOREL Ankeny™ Mid Hiker $135.00 Rated: 4 stars!

View More Like This Merrell - Freewheel Mesh Chukka
Merrell Freewheel Mesh Chukka $100.00 Rated: 4 stars!
Bed Stu - Hoover
Bed Stu Hoover $175.00 Rated: 4 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!
UGG - Leighton Waterproof
UGG Leighton Waterproof $169.95

View More Like This Calvin Klein - Jae
Calvin Klein Jae $140.00 $97.99 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 UGG - Larken Stripe Perf
UGG Larken Stripe Perf $169.95 $113.87 Rated: 5 stars!

Rockport - Wynstin Chukka
Rockport Wynstin Chukka $119.95
View More Like This Chaco - Montrose Chukka
Chaco Montrose Chukka $139.95 Rated: 5 stars!
View More Like This Sebago - Turner Chukka Waterproof
Sebago Turner Chukka Waterproof $139.95 Rated: 3 stars!
Justin - Cappie Steel Toe
Justin Cappie Steel Toe $99.00

View More Like This Vivobarefoot - Gobi II M Leather
Vivobarefoot Gobi II M Leather $155.00 Rated: 4 stars!
SOREL - Madson Chukka Waterproof
SOREL Madson Chukka Waterproof $170.00
SOREL - Madson Chukka Waterproof
SOREL Madson Chukka Waterproof $170.00
UGG - Leighton Waterproof
UGG Leighton Waterproof $169.95

Reef - Voyage Boot LE
Reef Voyage Boot LE $145.00
View More Like This Timberland - Westmore Leather Fabric Chukka
Timberland Westmore Leather Fabric Chukka $149.95 Rated: 4 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 Rated: 5 stars!

View More Like This Lacoste - Laccord Chukka 217 1
Lacoste Laccord Chukka 217 1 $159.95 $112.99 Rated: 5 stars!
View More Like This Chaco - Montrose Chukka
Chaco Montrose Chukka $139.95 Rated: 5 stars!
John Varvatos - Brooklyn Chukka
John Varvatos Brooklyn Chukka $228.00
NEW!
View More Like This UGG - Leighton Bomber
UGG Leighton Bomber $179.95 Rated: 4 stars!

View More Like This SOREL - Ankeny™ Mid Hiker
SOREL Ankeny™ Mid Hiker $135.00 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 UGG - Freamon Capra
UGG Freamon Capra $149.95 $100.47 Rated: 4 stars!
View More Like This UGG - Freamon Canvas
UGG Freamon Canvas $109.95 $73.67

Reef - Voyage Boot
Reef Voyage Boot $130.00
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 - Total Motion Fusion Desert Boot
Rockport Total Motion Fusion Desert Boot $149.95 Rated: 5 stars!
View More Like This Lacoste - Laccord Chukka 217 1
Lacoste Laccord Chukka 217 1 $159.95 $112.99 Rated: 5 stars!

View More Like This Timberland - Earthkeepers® Brook Park Chukka
Timberland Earthkeepers® Brook Park Chukka $110.00 $77.99 Rated: 5 stars!
View More Like This Caterpillar - Allay
Caterpillar Allay $110.00
View More Like This Irish Setter - Borderland Chukka
Irish Setter Borderland Chukka $190.00 $169.95 Rated: 4 stars!
View More Like This Calvin Klein - Kenley
Calvin Klein Kenley $130.00 $90.99

View More Like This Merrell - Freewheel Mesh Chukka
Merrell Freewheel Mesh Chukka $100.00 $69.99 Rated: 4 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 Justin - WK275
Justin WK275 $119.95 Rated: 3 stars!
John Varvatos - Brooklyn Chukka
John Varvatos Brooklyn Chukka $228.00
NEW!

View More Like This SOREL - Madson Chukka
SOREL Madson Chukka $170.00 $119.00 Rated: 4 stars!
View More Like This Sperry - Clipper Chukka
Sperry Clipper Chukka $120.00 Rated: 5 stars!
View More Like This UGG - Larken Stripe Perf
UGG Larken Stripe Perf $169.95 $113.87 Rated: 5 stars!
View More Like This UGG - Larken Stripe Perf
UGG Larken Stripe Perf $169.95 $113.87 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 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 Merrell - Brevard Chukka
Merrell Brevard Chukka $150.00 Rated: 2 stars!
View More Like This Cole Haan - 2.Zerogrand Chukka
Cole Haan 2.Zerogrand Chukka $320.00 $224.99

View More Like This Caterpillar - Mitch
Caterpillar Mitch $90.00 Rated: 5 stars!
View More Like This Danner - Wolf Creek Chukka
Danner Wolf Creek Chukka $180.00 Rated: 5 stars!
View More Like This Timberland - Carter Notch Waterproof Plain Toe Chukka
Timberland Carter Notch Waterproof Plain Toe Chukka $140.00 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!

John Varvatos - Brooklyn Chukka
John Varvatos Brooklyn Chukka $228.00
NEW!
View More Like This SOREL - Madson Chukka
SOREL Madson Chukka $170.00 $119.00 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 UGG - Freamon Canvas
UGG Freamon Canvas $109.95 $73.67

View More Like This Wolverine - Ranger 6
Wolverine Ranger 6" Moc Toe $140.00
View More Like This Wolverine - Cort Waterproof Leather Chukka
Wolverine Cort Waterproof Leather Chukka $160.00 Rated: 5 stars!
View More Like This UGG - Neumel
UGG Neumel $129.95 Rated: 4 stars!
View More Like This Jambu - Tavern
Jambu Tavern $189.00

View More Like This Harley-Davidson - Candler
Harley-Davidson Candler $150.00
View More Like This Timberland - Groveton Leather and Fabric Chukka
Timberland Groveton Leather and Fabric Chukka $80.00 $55.99 Rated: 5 stars!
View More Like This Merrell - Brevard Chukka
Merrell Brevard Chukka $150.00 Rated: 2 stars!
View More Like This Eastland 1955 Edition - Seneca
Eastland 1955 Edition Seneca $110.00 $99.95 Rated: 5 stars!

View More Like This Satorisan - Antai-Bokhara Antelope
Satorisan Antai-Bokhara Antelope $257.00 $179.99 Rated: 5 stars!
View More Like This Trask - Arlington
Trask Arlington $275.00 Rated: 5 stars!
View More Like This OluKai - Pahoa
OluKai Pahoa $200.00 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 Cole Haan - 2.Zerogrand Chukka
Cole Haan 2.Zerogrand Chukka $320.00 $224.99
View More Like This Caterpillar - Mitch
Caterpillar Mitch $90.00 Rated: 5 stars!
View More Like This Wolverine - Ranger 6
Wolverine Ranger 6" Moc Toe $135.00
View More Like This Wolverine - Ranger 6
Wolverine Ranger 6" Moc Toe $135.00

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