Skip to search results Skip to filters Skip to sort Skip to selected filters

Men's Chukka Boots

176 items found

Sort By

Your Selections

Search Results

Clarks - Desert Boot. Color Beeswax 1. $150.00. 4.5 out of 5 stars

Brown Clarks Desert Boot

Brown Clarks Desert Boot

+8

Brand Name: Clarks
Product Name: Desert Boot
Gender: Men's
Color: Beeswax 1
Price: $150.00
Rating: 4Rated 4 stars out of 5(752)

Clarks - Wallabee Boot. Color Black Suede. $170.00. 4.7 out of 5 stars

Black Clarks Wallabee Boot

Black Clarks Wallabee Boot

+5

Brand Name: Clarks
Product Name: Wallabee Boot
Gender: Men's
Color: Black Suede
Price: $170.00
Rating: 5Rated 5 stars out of 5(43)

Ariat - Lookout. Color Foothill Brown. $149.95. 4.2 out of 5 stars

Brown Ariat Lookout

Brown Ariat Lookout

Brand Name: Ariat
Product Name: Lookout
Gender: Men's
Color: Foothill Brown
Price: $149.95
Rating: 4Rated 4 stars out of 5(126)

Red Wing Heritage - Work Chukka. Color Briar Oil Slick. $289.99. 4.5 out of 5 stars

Mahogany Red Wing Heritage Work Chukka

Mahogany Red Wing Heritage Work Chukka

Brand Name: Red Wing Heritage
Product Name: Work Chukka
Gender: Men's
Color: Briar Oil Slick
Price: $289.99
Rating: 4Rated 4 stars out of 5(87)

COACH - Suede Chukka Boot. Color Black. On sale for $224.20. MSRP $295.00..

Black COACH Suede Chukka Boot

Black COACH Suede Chukka Boot

Brand Name: COACH
Product Name: Suede Chukka Boot
Gender: Men's
Color: Black
Price: $224.20MSRP: $295.00
Rating

Johnston & Murphy Collection - Jenson Chukka. Color Brown Italian Calfskin. Low Stock. $295.00. 2.5 out of 5 stars

10 left in stock

Brown Johnston & Murphy Collection Jenson Chukka

Brown Johnston & Murphy Collection Jenson Chukka

+2

Brand Name: Johnston & Murphy Collection
Product Name: Jenson Chukka
Gender: Men's
Color: Brown Italian Calfskin
Price: $295.00
Rating: 3Rated 3 stars out of 5(2)

. Clarks - Desert Coal. Color Stone Suede. On sale for $123.50. MSRP $160.00.. 4.9 out of 5 stars

Gray Clarks Desert Coal

Gray Clarks Desert Coal

+4

Brand Name: Clarks
Product Name: Desert Coal
Gender: Men's
Color: Stone Suede
Price: $123.50MSRP: $160.00
Rating: 5Rated 5 stars out of 5(10)

Clarks - Bushacre 3. Color Sand Waxy Suede. $109.95. 4.0 out of 5 stars

Beige Clarks Bushacre 3

Beige Clarks Bushacre 3

+6

Brand Name: Clarks
Product Name: Bushacre 3
Gender: Men's
Color: Sand Waxy Suede
Price: $109.95
Rating: 4Rated 4 stars out of 5(166)

Stacy Adams - Martfield Chukka Boot. Color Mocha. On sale for $117.00. MSRP $130.00.. 5.0 out of 5 stars

Brown Stacy Adams Martfield Chukka Boot

Brown Stacy Adams Martfield Chukka Boot

+4

Brand Name: Stacy Adams
Product Name: Martfield Chukka Boot
Gender: Men's
Color: Mocha
Price: $117.00MSRP: $130.00
Rating: 5Rated 5 stars out of 5(8)

Dockers - Norton. Color Taupe. On sale for $49.99. MSRP $85.00.. 3.7 out of 5 stars

Taupe Dockers Norton

Taupe Dockers Norton

+3

Brand Name: Dockers
Product Name: Norton
Gender: Men's
Color: Taupe
Price: $49.99MSRP: $85.00
Rating: 4Rated 4 stars out of 5(3)

Clarks - Shacre Boot. Color Black Suede. On sale for $81.36. MSRP $110.00.. 4.5 out of 5 stars

Black Clarks Shacre Boot

Black Clarks Shacre Boot

+5

Brand Name: Clarks
Product Name: Shacre Boot
Gender: Men's
Color: Black Suede
Price: $81.36MSRP: $110.00
Rating: 4Rated 4 stars out of 5(59)

TOMS - Travel Lite Moc Chukka. Color Dark Brown. On sale for $98.48. MSRP $119.95..

Brown TOMS Travel Lite Moc Chukka

Brown TOMS Travel Lite Moc Chukka

Brand Name: TOMS
Product Name: Travel Lite Moc Chukka
Gender: Men's
Color: Dark Brown
Price: $98.48MSRP: $119.95
Rating

. Steve Madden - Hestonn. Color Tobacco Suede. $90.00. 3.8 out of 5 stars

Brown Steve Madden Hestonn

Brown Steve Madden Hestonn

+3

Brand Name: Steve Madden
Product Name: Hestonn
Gender: Men's
Color: Tobacco Suede
Price: $90.00
Rating: 4Rated 4 stars out of 5(69)

UGG - Neumel. Color Charcoal Suede. $139.95. 4.8 out of 5 stars

Gray UGG Neumel

Gray UGG Neumel

+10

Brand Name: UGG
Product Name: Neumel
Gender: Men's
Color: Charcoal Suede
Price: $139.95
Rating: 5Rated 5 stars out of 5(5978)

Clarks - Brahnz Mid. Color Navy Nubuck. On sale for $104.45. MSRP $110.00.. 4.8 out of 5 stars

Blue Clarks Brahnz Mid

Blue Clarks Brahnz Mid

Brand Name: Clarks
Product Name: Brahnz Mid
Gender: Men's
Color: Navy Nubuck
Price: $104.45MSRP: $110.00
Rating: 5Rated 5 stars out of 5(6)

Clarks - Corston Wally Waterproof. Color Dark Sand Waxy Suede Warmlined Waterproof. On sale for $74.95. MSRP $170.00.. 3.0 out of 5 stars

Tan Clarks Corston Wally Waterproof

Tan Clarks Corston Wally Waterproof

Brand Name: Clarks
Product Name: Corston Wally Waterproof
Gender: Men's
Color: Dark Sand Waxy Suede Warmlined Waterproof
Price: $74.95MSRP: $170.00
Rating: 3Rated 3 stars out of 5(1)

UGG - Neumel Crafted Regenerate. Color Chestnut. $199.95. 4.0 out of 5 stars

Brown UGG Neumel Crafted Regenerate

Brown UGG Neumel Crafted Regenerate

Brand Name: UGG
Product Name: Neumel Crafted Regenerate
Gender: Unisex
Color: Chestnut
Price: $199.95
Rating: 4Rated 4 stars out of 5(8)

Clarks - Desert Boot Evo. Color Black Suede. $140.00. 3.8 out of 5 stars

Black Clarks Desert Boot Evo

Black Clarks Desert Boot Evo

+4

Brand Name: Clarks
Product Name: Desert Boot Evo
Gender: Men's
Color: Black Suede
Price: $140.00
Rating: 4Rated 4 stars out of 5(14)

Dockers - Nigel. Color Dark Brown. On sale for $69.99. MSRP $95.00..

Brown Dockers Nigel

Brown Dockers Nigel

+2

Brand Name: Dockers
Product Name: Nigel
Gender: Men's
Color: Dark Brown
Price: $69.99MSRP: $95.00
Rating

UGG - Neumel Weather Hybrid. Color Chestnut/Whitecap. $179.95. 4.3 out of 5 stars

Yellow UGG Neumel Weather Hybrid

Yellow UGG Neumel Weather Hybrid

Brand Name: UGG
Product Name: Neumel Weather Hybrid
Gender: Men's
Color: Chestnut/Whitecap
Price: $179.95
Rating: 4Rated 4 stars out of 5(41)

UGG - Burleigh Chukka. Color Chestnut. $159.95. 4.9 out of 5 stars

Brown UGG Burleigh Chukka

Brown UGG Burleigh Chukka

+2

Brand Name: UGG
Product Name: Burleigh Chukka
Gender: Men's
Color: Chestnut
Price: $159.95
Rating: 5Rated 5 stars out of 5(9)

UGG - Neumel Moc. Color Chestnut. $149.95. 4.6 out of 5 stars

Brown UGG Neumel Moc

Brown UGG Neumel Moc

+2

Brand Name: UGG
Product Name: Neumel Moc
Gender: Men's
Color: Chestnut
Price: $149.95
Rating: 5Rated 5 stars out of 5(98)

. TOMS - Navi. Color Water Resistant Topaz Brown Leather. On sale for $125.52. MSRP $139.95.. 3.9 out of 5 stars

Brown TOMS Navi

Brown TOMS Navi

+2

Brand Name: TOMS
Product Name: Navi
Gender: Men's
Color: Water Resistant Topaz Brown Leather
Price: $125.52MSRP: $139.95
Rating: 4Rated 4 stars out of 5(27)

Florsheim - Lodge Plain Toe Chukka Boot. Color Brown Crazy Horse. $129.95. 4.5 out of 5 stars

Brown Florsheim Lodge Plain Toe Chukka Boot

Brown Florsheim Lodge Plain Toe Chukka Boot

+3

Brand Name: Florsheim
Product Name: Lodge Plain Toe Chukka Boot
Gender: Men's
Color: Brown Crazy Horse
Price: $129.95
Rating: 5Rated 5 stars out of 5(108)

Rockport - Classic Break Chukka. Color Dark Brown Leather. On sale for $89.99. MSRP $139.95.. 4.3 out of 5 stars

Brown Rockport Classic Break Chukka

Brown Rockport Classic Break Chukka

Brand Name: Rockport
Product Name: Classic Break Chukka
Gender: Men's
Color: Dark Brown Leather
Price: $89.99MSRP: $139.95
Rating: 4Rated 4 stars out of 5(210)

Steve Madden - Harken. Color Cognac Leather. $89.95. 4.1 out of 5 stars

Brown Steve Madden Harken

Brown Steve Madden Harken

+2

Brand Name: Steve Madden
Product Name: Harken
Gender: Men's
Color: Cognac Leather
Price: $89.95
Rating: 4Rated 4 stars out of 5(114)

Red Wing Heritage - Weekend Chukka. Color Copper Rough & Tough. $249.99. 4.3 out of 5 stars

Tan Red Wing Heritage Weekend Chukka

Tan Red Wing Heritage Weekend Chukka

Brand Name: Red Wing Heritage
Product Name: Weekend Chukka
Gender: Men's
Color: Copper Rough & Tough
Price: $249.99
Rating: 4Rated 4 stars out of 5(49)

Johnston & Murphy - Upton Chukka. Color Tan Oiled Full Grain. $169.00. 4.7 out of 5 stars

Tan Johnston & Murphy Upton Chukka

Tan Johnston & Murphy Upton Chukka

+2

Brand Name: Johnston & Murphy
Product Name: Upton Chukka
Gender: Men's
Color: Tan Oiled Full Grain
Price: $169.00
Rating: 5Rated 5 stars out of 5(41)

SOREL - Carson™ Chukka WP. Color Elk/Oatmeal. On sale for $103.87. MSRP $160.00.. 3.6 out of 5 stars

Brown SOREL Carson™ Chukka WP

Brown SOREL Carson™ Chukka WP

+1

Brand Name: SOREL
Product Name: Carson™ Chukka WP
Gender: Men's
Color: Elk/Oatmeal
Price: $103.87MSRP: $160.00
Rating: 4Rated 4 stars out of 5(11)

Florsheim - Norwalk Plain Toe Chukka Boot. Color Cognac Milled Leather. On sale for $121.45. MSRP $135.00.. 4.6 out of 5 stars

Brown Florsheim Norwalk Plain Toe Chukka Boot

Brown Florsheim Norwalk Plain Toe Chukka Boot

Brand Name: Florsheim
Product Name: Norwalk Plain Toe Chukka Boot
Gender: Men's
Color: Cognac Milled Leather
Price: $121.45MSRP: $135.00
Rating: 5Rated 5 stars out of 5(46)

Johnston & Murphy - Upton Chukka Boot. Color Tan Full Grain. $169.00. 4.7 out of 5 stars

Tan Johnston & Murphy Upton Chukka Boot

Tan Johnston & Murphy Upton Chukka Boot

Brand Name: Johnston & Murphy
Product Name: Upton Chukka Boot
Gender: Men's
Color: Tan Full Grain
Price: $169.00
Rating: 5Rated 5 stars out of 5(40)

Nunn Bush - Otto Plain Toe Chukka Boot. Color Gray. On sale for $79.99. MSRP $95.00.. 4.3 out of 5 stars

Gray Nunn Bush Otto Plain Toe Chukka Boot

Gray Nunn Bush Otto Plain Toe Chukka Boot

+4

Brand Name: Nunn Bush
Product Name: Otto Plain Toe Chukka Boot
Gender: Men's
Color: Gray
Price: $79.99MSRP: $95.00
Rating: 4Rated 4 stars out of 5(15)

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Tan CH. On sale for $84.99. MSRP $115.00.. 4.3 out of 5 stars

Brown Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

Brown Nunn Bush Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology

+3

Brand Name: Nunn Bush
Product Name: Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology
Gender: Men's
Color: Tan CH
Price: $84.99MSRP: $115.00
Rating: 4Rated 4 stars out of 5(130)

Nunn Bush - Denali Plain Toe Chukka. Color Black. On sale for $89.95. MSRP $115.00.. 4.5 out of 5 stars

Black Nunn Bush Denali Plain Toe Chukka

Black Nunn Bush Denali Plain Toe Chukka

+3

Brand Name: Nunn Bush
Product Name: Denali Plain Toe Chukka
Gender: Men's
Color: Black
Price: $89.95MSRP: $115.00
Rating: 4Rated 4 stars out of 5(80)

Marc Joseph New York - Soho Boot. Color Cafe Grainy. On sale for $81.90. MSRP $195.00.. 5.0 out of 5 stars

Brown Marc Joseph New York Soho Boot

Brown Marc Joseph New York Soho Boot

+3

Brand Name: Marc Joseph New York
Product Name: Soho Boot
Gender: Men's
Color: Cafe Grainy
Price: $81.90MSRP: $195.00
Rating: 5Rated 5 stars out of 5(1)

Born - Theo. Color Taupe/Brown Distressed. $130.00.

Brown Born Theo

Brown Born Theo

Brand Name: Born
Product Name: Theo
Gender: Men's
Color: Taupe/Brown Distressed
Price: $130.00
Rating

Johnston & Murphy - Barrett Chukka. Color Tan Full Grain. On sale for $99.99. MSRP $175.00..

Tan Johnston & Murphy Barrett Chukka

Tan Johnston & Murphy Barrett Chukka

Brand Name: Johnston & Murphy
Product Name: Barrett Chukka
Gender: Men's
Color: Tan Full Grain
Price: $99.99MSRP: $175.00
Rating

Ariat - Spitfire H2O. Color Reliable Brown. On sale for $139.95. MSRP $149.95.. 4.5 out of 5 stars

Brown Ariat Spitfire H2O

Brown Ariat Spitfire H2O

+2

Brand Name: Ariat
Product Name: Spitfire H2O
Gender: Men's
Color: Reliable Brown
Price: $139.95MSRP: $149.95
Rating: 5Rated 5 stars out of 5(31)

Sperry - A/O Plushwave Lug Chukka. Color Brown 1. $139.95. 4.2 out of 5 stars

Brown Sperry A/O Plushwave Lug Chukka

Brown Sperry A/O Plushwave Lug Chukka

+3

Brand Name: Sperry
Product Name: A/O Plushwave Lug Chukka
Gender: Men's
Color: Brown 1
Price: $139.95
Rating: 4Rated 4 stars out of 5(33)

Born - Brock. Color Brown Distressed Leather. $140.00. 4.6 out of 5 stars

Brown Born Brock

Brown Born Brock

+1

Brand Name: Born
Product Name: Brock
Gender: Men's
Color: Brown Distressed Leather
Price: $140.00
Rating: 5Rated 5 stars out of 5(13)

Vince Camuto - Tadesse Chukka Boot. Color Mocha. On sale for $109.98. MSRP $179.00..

Brown Vince Camuto Tadesse Chukka Boot

Brown Vince Camuto Tadesse Chukka Boot

Brand Name: Vince Camuto
Product Name: Tadesse Chukka Boot
Gender: Men's
Color: Mocha
Price: $109.98MSRP: $179.00
Rating

Stacy Adams - Kyron Chukka Boot. Color Brown Multi. On sale for $39.98. MSRP $115.00.. 4.0 out of 5 stars

Brown Stacy Adams Kyron Chukka Boot

Brown Stacy Adams Kyron Chukka Boot

+2

Brand Name: Stacy Adams
Product Name: Kyron Chukka Boot
Gender: Men's
Color: Brown Multi
Price: $39.98MSRP: $115.00
Rating: 4Rated 4 stars out of 5(2)

Twisted X - MDM0033. Color Bomber/Tan. $135.95. 5.0 out of 5 stars

Brown Twisted X MDM0033

Brown Twisted X MDM0033

Brand Name: Twisted X
Product Name: MDM0033
Gender: Men's
Color: Bomber/Tan
Price: $135.95
Rating: 5Rated 5 stars out of 5(7)

Dr. Martens - Church Quad Archive. Color Dark Brown Crazy Horse. On sale for $169.95. MSRP $200.00..

Brown Dr. Martens Church Quad Archive

Brown Dr. Martens Church Quad Archive

Brand Name: Dr. Martens
Product Name: Church Quad Archive
Gender: Unisex
Color: Dark Brown Crazy Horse
Price: $169.95MSRP: $200.00
Rating

Frye - Bowery Chukka. Color Black. On sale for $226.28. MSRP $328.00.. 3.5 out of 5 stars

Black Frye Bowery Chukka

Black Frye Bowery Chukka

+2

Brand Name: Frye
Product Name: Bowery Chukka
Gender: Men's
Color: Black
Price: $226.28MSRP: $328.00
Rating: 3Rated 3 stars out of 5(11)

Bruno Magli - Taddeo. Color Black. Low Stock. On sale for $326.25. MSRP $375.00..

3 left in stock

Black Bruno Magli Taddeo

Black Bruno Magli Taddeo

+2

Brand Name: Bruno Magli
Product Name: Taddeo
Gender: Men's
Color: Black
Price: $326.25MSRP: $375.00
Rating

Marc Joseph New York - Chicago. Color Black Grainy. On sale for $89.95. MSRP $195.00..

Black Marc Joseph New York Chicago

Black Marc Joseph New York Chicago

+2 colors/patterns

Brand Name: Marc Joseph New York
Product Name: Chicago
Gender: Men's
Color: Black Grainy
Price: $89.95MSRP: $195.00
Rating

SOREL - Explorer Next™ Drift Waterproof. Color Tobacco/Sea Salt. On sale for $83.66. MSRP $135.00.. 4.6 out of 5 stars

Brown SOREL Explorer Next™ Drift Waterproof

Brown SOREL Explorer Next™ Drift Waterproof

+3

Brand Name: SOREL
Product Name: Explorer Next™ Drift Waterproof
Gender: Men's
Color: Tobacco/Sea Salt
Price: $83.66MSRP: $135.00
Rating: 5Rated 5 stars out of 5(16)

Cole Haan - Original Grand Chukka. Color Woodbury Leather/Dark Roast. On sale for $72.00. MSRP $180.00.. 4.6 out of 5 stars

Brown Cole Haan Original Grand Chukka

Brown Cole Haan Original Grand Chukka

+2

Brand Name: Cole Haan
Product Name: Original Grand Chukka
Gender: Men's
Color: Woodbury Leather/Dark Roast
Price: $72.00MSRP: $180.00
Rating: 5Rated 5 stars out of 5(426)

Johnston & Murphy - XC Flex Raleigh Chukka. Color Tan Full Grain. $175.00. 4.3 out of 5 stars

Tan Johnston & Murphy XC Flex Raleigh Chukka

Tan Johnston & Murphy XC Flex Raleigh Chukka

Brand Name: Johnston & Murphy
Product Name: XC Flex Raleigh Chukka
Gender: Men's
Color: Tan Full Grain
Price: $175.00
Rating: 4Rated 4 stars out of 5(50)

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Cognac. On sale for $99.09. MSRP $125.00.. 4.8 out of 5 stars

Tan Stacy Adams Maxwell Plain Toe Demi Boot

Tan Stacy Adams Maxwell Plain Toe Demi Boot

+2

Brand Name: Stacy Adams
Product Name: Maxwell Plain Toe Demi Boot
Gender: Men's
Color: Cognac
Price: $99.09MSRP: $125.00
Rating: 5Rated 5 stars out of 5(34)

Cole Haan - Hawthorne Chukka Boot. Color British Tan. On sale for $80.00. MSRP $140.00.. 4.5 out of 5 stars

Tan Cole Haan Hawthorne Chukka Boot

Tan Cole Haan Hawthorne Chukka Boot

+3

Brand Name: Cole Haan
Product Name: Hawthorne Chukka Boot
Gender: Men's
Color: British Tan
Price: $80.00MSRP: $140.00
Rating: 5Rated 5 stars out of 5(11)

ALDO - Kenora. Color Other Brown. On sale for $92.26. MSRP $130.00.. 5.0 out of 5 stars

Brown ALDO Kenora

Brown ALDO Kenora

+2

Brand Name: ALDO
Product Name: Kenora
Gender: Men's
Color: Other Brown
Price: $92.26MSRP: $130.00
Rating: 5Rated 5 stars out of 5(2)

ALDO - Watson. Color Cognac. On sale for $107.44. MSRP $130.00..

Tan ALDO Watson

Tan ALDO Watson

+2

Brand Name: ALDO
Product Name: Watson
Gender: Men's
Color: Cognac
Price: $107.44MSRP: $130.00
Rating

Clarks - Atticus LT Hi. Color Dark Brown Leather. On sale for $116.95. MSRP $130.00..

Brown Clarks Atticus LT Hi

Brown Clarks Atticus LT Hi

Brand Name: Clarks
Product Name: Atticus LT Hi
Gender: Men's
Color: Dark Brown Leather
Price: $116.95MSRP: $130.00
Rating

Eastland 1955 Edition - Seneca. Color Oak. Low Stock. On sale for $89.95. MSRP $120.00.. 4.4 out of 5 stars

8 left in stock

Brown Eastland 1955 Edition Seneca

Brown Eastland 1955 Edition Seneca

+3

Brand Name: Eastland 1955 Edition
Product Name: Seneca
Gender: Men's
Color: Oak
Price: $89.95MSRP: $120.00
Rating: 4Rated 4 stars out of 5(42)

Marc Joseph New York - Lenox Ave. Color Navy Washed Grainy. On sale for $78.00. MSRP $195.00.. 3.3 out of 5 stars

Navy Marc Joseph New York Lenox Ave

Navy Marc Joseph New York Lenox Ave

+2

Brand Name: Marc Joseph New York
Product Name: Lenox Ave
Gender: Men's
Color: Navy Washed Grainy
Price: $78.00MSRP: $195.00
Rating: 3Rated 3 stars out of 5(7)

ECCO - Grainer Chukka Boot. Color Black. On sale for $171.00. MSRP $190.00.. 4.0 out of 5 stars

Black ECCO Grainer Chukka Boot

Black ECCO Grainer Chukka Boot

+2

Brand Name: ECCO
Product Name: Grainer Chukka Boot
Gender: Men's
Color: Black
Price: $171.00MSRP: $190.00
Rating: 4Rated 4 stars out of 5(1)

Florsheim - Renegade Plain Toe Chukka Boot. Color Brown. On sale for $127.50. MSRP $150.00.. 4.3 out of 5 stars

Brown Florsheim Renegade Plain Toe Chukka Boot

Brown Florsheim Renegade Plain Toe Chukka Boot

+1

Brand Name: Florsheim
Product Name: Renegade Plain Toe Chukka Boot
Gender: Men's
Color: Brown
Price: $127.50MSRP: $150.00
Rating: 4Rated 4 stars out of 5(18)

La Canadienne - Alston. Color Taupe Suede. On sale for $340.00. MSRP $425.00..

Taupe La Canadienne Alston

Taupe La Canadienne Alston

Brand Name: La Canadienne
Product Name: Alston
Gender: Men's
Color: Taupe Suede
Price: $340.00MSRP: $425.00
Rating

Cole Haan - Originalgrand Chukka Waterproof. Color Navy Blazer Nubuck/Birch Waterproof. Low Stock. On sale for $133.99. MSRP $250.00.. 4.6 out of 5 stars

3 left in stock

Navy Cole Haan Originalgrand Chukka Waterproof

Navy Cole Haan Originalgrand Chukka Waterproof

Brand Name: Cole Haan
Product Name: Originalgrand Chukka Waterproof
Gender: Men's
Color: Navy Blazer Nubuck/Birch Waterproof
Price: $133.99MSRP: $250.00
Rating: 5Rated 5 stars out of 5(29)

Twisted X - MDM0049. Color Bomber. $129.95. 4.0 out of 5 stars

Bone Twisted X MDM0049

Bone Twisted X MDM0049

Brand Name: Twisted X
Product Name: MDM0049
Gender: Men's
Color: Bomber
Price: $129.95
Rating: 4Rated 4 stars out of 5(4)

ALDO - Clinton. Color Black. $129.99.

Black ALDO Clinton

Black ALDO Clinton

+2

Brand Name: ALDO
Product Name: Clinton
Gender: Men's
Color: Black
Price: $129.99
Rating

Vince Camuto - Stuwert Casual Boot. Color Avola/Mocha. Low Stock. On sale for $101.06. MSRP $169.00.. 4.0 out of 5 stars

7 left in stock

Brown Vince Camuto Stuwert Casual Boot

Brown Vince Camuto Stuwert Casual Boot

Brand Name: Vince Camuto
Product Name: Stuwert Casual Boot
Gender: Men's
Color: Avola/Mocha
Price: $101.06MSRP: $169.00
Rating: 4Rated 4 stars out of 5(1)

Koolaburra by UGG - Asaiah. Color Chestnut. Low Stock. $94.99. 4.0 out of 5 stars

7 left in stock

Brown Koolaburra by UGG Asaiah

Brown Koolaburra by UGG Asaiah

+2

Brand Name: Koolaburra by UGG
Product Name: Asaiah
Gender: Men's
Color: Chestnut
Price: $94.99
Rating: 4Rated 4 stars out of 5(2)

Marc Joseph New York - Smith ST. Color Black Grainy/Suede. On sale for $173.55. MSRP $195.00..

Black Marc Joseph New York Smith ST

Black Marc Joseph New York Smith ST

+2

Brand Name: Marc Joseph New York
Product Name: Smith ST
Gender: Men's
Color: Black Grainy/Suede
Price: $173.55MSRP: $195.00
Rating

Steve Madden - Hestonn - Extended Sizes. Color Tan Leather. On sale for $89.99. MSRP $95.00.. 3.9 out of 5 stars

Tan Steve Madden Hestonn - Extended Sizes

Tan Steve Madden Hestonn - Extended Sizes

Brand Name: Steve Madden
Product Name: Hestonn - Extended Sizes
Gender: Men's
Color: Tan Leather
Price: $89.99MSRP: $95.00
Rating: 4Rated 4 stars out of 5(59)

Steve Madden - Harken - Extended Sizes. Color Black. $95.00. 4.1 out of 5 stars

Black Steve Madden Harken - Extended Sizes

Black Steve Madden Harken - Extended Sizes

+2

Brand Name: Steve Madden
Product Name: Harken - Extended Sizes
Gender: Men's
Color: Black
Price: $95.00
Rating: 4Rated 4 stars out of 5(115)

Ariat - Spitfire Outdoor Waterproof. Color Oily Distressed Brown. $149.95. 4.3 out of 5 stars

Tan Ariat Spitfire Outdoor Waterproof

Tan Ariat Spitfire Outdoor Waterproof

Brand Name: Ariat
Product Name: Spitfire Outdoor Waterproof
Gender: Men's
Color: Oily Distressed Brown
Price: $149.95
Rating: 4Rated 4 stars out of 5(20)

Barbour - Barbour Readhead. Color Black. Low Stock. On sale for $154.00. MSRP $220.00..

7 left in stock

Black Barbour Barbour Readhead

Black Barbour Barbour Readhead

+2

Brand Name: Barbour
Product Name: Barbour Readhead
Gender: Men's
Color: Black
Price: $154.00MSRP: $220.00
Rating

BOSS - Calev Leather Desert Boot. Color Dark Brown. Low Stock. On sale for $207.00. MSRP $230.00..

8 left in stock

Brown BOSS Calev Leather Desert Boot

Brown BOSS Calev Leather Desert Boot

Brand Name: BOSS
Product Name: Calev Leather Desert Boot
Gender: Men's
Color: Dark Brown
Price: $207.00MSRP: $230.00
Rating

Florsheim - Trail Mix Plain Toe Chukka Boot. Color Brown Crazy Horse. On sale for $89.95. MSRP $120.00.. 4.6 out of 5 stars

Brown Florsheim Trail Mix Plain Toe Chukka Boot

Brown Florsheim Trail Mix Plain Toe Chukka Boot

Brand Name: Florsheim
Product Name: Trail Mix Plain Toe Chukka Boot
Gender: Men's
Color: Brown Crazy Horse
Price: $89.95MSRP: $120.00
Rating: 5Rated 5 stars out of 5(34)

Ariat - Clean Country. Color Dark Tan. $119.95. 4.5 out of 5 stars

Brown Ariat Clean Country

Brown Ariat Clean Country

+2

Brand Name: Ariat
Product Name: Clean Country
Gender: Men's
Color: Dark Tan
Price: $119.95
Rating: 5Rated 5 stars out of 5(11)

Stacy Adams - Tilden Chukka Boot. Color Black. On sale for $56.37. MSRP $119.95.. 3.8 out of 5 stars

Black Stacy Adams Tilden Chukka Boot

Black Stacy Adams Tilden Chukka Boot

+2

Brand Name: Stacy Adams
Product Name: Tilden Chukka Boot
Gender: Men's
Color: Black
Price: $56.37MSRP: $119.95
Rating: 4Rated 4 stars out of 5(6)

Johnston & Murphy Collection - Everson Alpine Boot. Color Tan Italian Calfskin. Low Stock. On sale for $214.50. MSRP $325.00..

9 left in stock

Tan Johnston & Murphy Collection Everson Alpine Boot

Tan Johnston & Murphy Collection Everson Alpine Boot

Brand Name: Johnston & Murphy Collection
Product Name: Everson Alpine Boot
Gender: Men's
Color: Tan Italian Calfskin
Price: $214.50MSRP: $325.00
Rating

Thomas & Vine - Keegan. Color Cognac. Low Stock. On sale for $86.94. MSRP $149.99.. 4.0 out of 5 stars

9 left in stock

Tan Thomas & Vine Keegan

Tan Thomas & Vine Keegan

+2

Brand Name: Thomas & Vine
Product Name: Keegan
Gender: Men's
Color: Cognac
Price: $86.94MSRP: $149.99
Rating: 4Rated 4 stars out of 5(1)

Twisted X - MCA0007. Color Oiled Saddle. $164.95. 3.7 out of 5 stars

Tan Twisted X MCA0007

Tan Twisted X MCA0007

Brand Name: Twisted X
Product Name: MCA0007
Gender: Men's
Color: Oiled Saddle
Price: $164.95
Rating: 4Rated 4 stars out of 5(3)

Twisted X - MDM0014. Color Copper. $129.95. 5.0 out of 5 stars

Bronze Twisted X MDM0014

Bronze Twisted X MDM0014

Brand Name: Twisted X
Product Name: MDM0014
Gender: Men's
Color: Copper
Price: $129.95
Rating: 5Rated 5 stars out of 5(5)

Twisted X - MDM0019. Color Bomber/Neon Orange. $129.95. 4.9 out of 5 stars

Brown Twisted X MDM0019

Brown Twisted X MDM0019

Brand Name: Twisted X
Product Name: MDM0019
Gender: Men's
Color: Bomber/Neon Orange
Price: $129.95
Rating: 5Rated 5 stars out of 5(7)

Twisted X - MDM0057. Color Oiled Saddle/Midnight. $135.95. 5.0 out of 5 stars

Brown Twisted X MDM0057

Brown Twisted X MDM0057

Brand Name: Twisted X
Product Name: MDM0057
Gender: Men's
Color: Oiled Saddle/Midnight
Price: $135.95
Rating: 5Rated 5 stars out of 5(3)

Ariat - Recon Country Boots. Color Dirty Taupe Suede. $149.95. 4.1 out of 5 stars

Neutral Ariat Recon Country Boots

Neutral Ariat Recon Country Boots

+2

Brand Name: Ariat
Product Name: Recon Country Boots
Gender: Men's
Color: Dirty Taupe Suede
Price: $149.95
Rating: 4Rated 4 stars out of 5(31)

COACH - Spencer Boot. Color Saddle. Low Stock. On sale for $221.24. MSRP $295.00..

6 left in stock

Brown COACH Spencer Boot

Brown COACH Spencer Boot

Brand Name: COACH
Product Name: Spencer Boot
Gender: Men's
Color: Saddle
Price: $221.24MSRP: $295.00
Rating

Martin Dingman - Ernest Kudu. Color Evergreen. Low Stock. On sale for $316.00. MSRP $395.00..

6 left in stock

Green Martin Dingman Ernest Kudu

Green Martin Dingman Ernest Kudu

+2

Brand Name: Martin Dingman
Product Name: Ernest Kudu
Gender: Men's
Color: Evergreen
Price: $316.00MSRP: $395.00
Rating

Steve Madden - Yvor. Color Grey Suede. Low Stock. On sale for $126.00. MSRP $140.00.. 2.0 out of 5 stars

4 left in stock

Gray Steve Madden Yvor

Gray Steve Madden Yvor

Brand Name: Steve Madden
Product Name: Yvor
Gender: Men's
Color: Grey Suede
Price: $126.00MSRP: $140.00
Rating: 2Rated 2 stars out of 5(1)

Cole Haan - Grand Atlantic Chukka WR. Color Morel Nubuck Micro Perf. Low Stock. $150.00. 4.0 out of 5 stars

7 left in stock

Brown Cole Haan Grand Atlantic Chukka WR

Brown Cole Haan Grand Atlantic Chukka WR

Brand Name: Cole Haan
Product Name: Grand Atlantic Chukka WR
Gender: Men's
Color: Morel Nubuck Micro Perf
Price: $150.00
Rating: 4Rated 4 stars out of 5(1)

Ariat - Recon Country. Color Distressed Brown. $149.95. 4.2 out of 5 stars

Brown Ariat Recon Country

Brown Ariat Recon Country

Brand Name: Ariat
Product Name: Recon Country
Gender: Men's
Color: Distressed Brown
Price: $149.95
Rating: 4Rated 4 stars out of 5(35)

Deer Stags - Bangor. Color Redwood/Dark Brown. On sale for $54.99. MSRP $100.00.. 4.2 out of 5 stars

Brown Deer Stags Bangor

Brown Deer Stags Bangor

Brand Name: Deer Stags
Product Name: Bangor
Gender: Men's
Color: Redwood/Dark Brown
Price: $54.99MSRP: $100.00
Rating: 4Rated 4 stars out of 5(13)

To Boot New York - Richard. Color Cognac. Low Stock. $450.00.

6 left in stock

Tan To Boot New York Richard

Tan To Boot New York Richard

+1

Brand Name: To Boot New York
Product Name: Richard
Gender: Men's
Color: Cognac
Price: $450.00
Rating

Twisted X - MXC0005. Color Grey/Light Grey. Low Stock. $149.95. 4.2 out of 5 stars

7 left in stock

Gray Twisted X MXC0005

Gray Twisted X MXC0005

Brand Name: Twisted X
Product Name: MXC0005
Gender: Men's
Color: Grey/Light Grey
Price: $149.95
Rating: 4Rated 4 stars out of 5(5)

Steve Madden - Jabbar. Color Dark Tan. $99.95. 3.9 out of 5 stars

Brown Steve Madden Jabbar

Brown Steve Madden Jabbar

Brand Name: Steve Madden
Product Name: Jabbar
Gender: Men's
Color: Dark Tan
Price: $99.95
Rating: 4Rated 4 stars out of 5(42)

Frye - Bowery Chukka. Color Fog. Low Stock. $328.00.

8 left in stock

Gray Frye Bowery Chukka

Gray Frye Bowery Chukka

Brand Name: Frye
Product Name: Bowery Chukka
Gender: Men's
Color: Fog
Price: $328.00
Rating

Nunn Bush - Circuit DC Plain Toe Chukka. Color Black. On sale for $59.95. MSRP $85.00.. 3.8 out of 5 stars

Black Nunn Bush Circuit DC Plain Toe Chukka

Black Nunn Bush Circuit DC Plain Toe Chukka

+3

Brand Name: Nunn Bush
Product Name: Circuit DC Plain Toe Chukka
Gender: Men's
Color: Black
Price: $59.95MSRP: $85.00
Rating: 4Rated 4 stars out of 5(32)

Born - Harrison. Color Brown Full Grain. $135.00. 4.3 out of 5 stars

Brown Born Harrison

Brown Born Harrison

+2

Brand Name: Born
Product Name: Harrison
Gender: Men's
Color: Brown Full Grain
Price: $135.00
Rating: 4Rated 4 stars out of 5(111)

Twisted X - MDM0003. Color Bomber. $129.95. 4.5 out of 5 stars

Bone Twisted X MDM0003

Bone Twisted X MDM0003

Brand Name: Twisted X
Product Name: MDM0003
Gender: Men's
Color: Bomber
Price: $129.95
Rating: 5Rated 5 stars out of 5(24)

Twisted X - MXC0001. Color Brown. $149.95. 4.4 out of 5 stars

Brown Twisted X MXC0001

Brown Twisted X MXC0001

Brand Name: Twisted X
Product Name: MXC0001
Gender: Men's
Color: Brown
Price: $149.95
Rating: 4Rated 4 stars out of 5(7)

Nunn Bush - Chase Plain Toe Chukka Contemporary Fashion Boot. Color Brandy. On sale for $59.95. MSRP $90.00.. 4.2 out of 5 stars

Brown Nunn Bush Chase Plain Toe Chukka Contemporary Fashion Boot

Brown Nunn Bush Chase Plain Toe Chukka Contemporary Fashion Boot

+3

Brand Name: Nunn Bush
Product Name: Chase Plain Toe Chukka Contemporary Fashion Boot
Gender: Men's
Color: Brandy
Price: $59.95MSRP: $90.00
Rating: 4Rated 4 stars out of 5(9)

SOREL - Madson™ II Chukka Waterproof. Color Tawny Buff. On sale for $156.24. MSRP $190.00.. 4.5 out of 5 stars

Tan SOREL Madson™ II Chukka Waterproof

Tan SOREL Madson™ II Chukka Waterproof

+4

Brand Name: SOREL
Product Name: Madson™ II Chukka Waterproof
Gender: Men's
Color: Tawny Buff
Price: $156.24MSRP: $190.00
Rating: 4Rated 4 stars out of 5(178)

Ariat - Spitfire. Color Sorrel Crunch. $119.95. 4.7 out of 5 stars

Brown Ariat Spitfire

Brown Ariat Spitfire

+4

Brand Name: Ariat
Product Name: Spitfire
Gender: Men's
Color: Sorrel Crunch
Price: $119.95
Rating: 5Rated 5 stars out of 5(296)

Dockers - Dartford. Color Dark Brown. On sale for $49.99. MSRP $85.00..

Brown Dockers Dartford

Brown Dockers Dartford

+3

Brand Name: Dockers
Product Name: Dartford
Gender: Men's
Color: Dark Brown
Price: $49.99MSRP: $85.00
Rating

Ariat - Hilo Rancher Moc. Color Tan. On sale for $69.97. MSRP $99.95.. 5.0 out of 5 stars

Tan Ariat Hilo Rancher Moc

Tan Ariat Hilo Rancher Moc

Brand Name: Ariat
Product Name: Hilo Rancher Moc
Gender: Men's
Color: Tan
Price: $69.97MSRP: $99.95
Rating: 5Rated 5 stars out of 5(7)

1 of 2

Get on the List

Subscribe to Zappos emails for exclusive product launches, early notifications for sales, and a few extra-special surprises.