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

Size 8.5 Brown Chukka Boots

52 items found

Sort By

Your Selections

Search Results

Ariat - Spitfire H2O. Color Old Earth. $149.95. 4.6 out of 5 stars

Brown Ariat Spitfire H2O

Brown Ariat Spitfire H2O

+2

Brand Name: Ariat
Product Name: Spitfire H2O
Gender: Men's
Color: Old Earth
Price: $149.95
Rating: 5Rated 5 stars out of 5(30)

Ariat - Spitfire. Color Old Earth. $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: Old Earth
Price: $119.95
Rating: 5Rated 5 stars out of 5(295)

Vince Camuto - Tadesse Chukka Boot. Color Mocha. On sale for $129.98. 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: $129.98MSRP: $179.00
Rating

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

9 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

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)

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

Brown Born Theo

Brown Born Theo

+3

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

Marc Joseph New York - Smith ST. Color Havana Grainy/Suede. On sale for $146.25. MSRP $195.00..

Brown Marc Joseph New York Smith ST

Brown Marc Joseph New York Smith ST

+2

Brand Name: Marc Joseph New York
Product Name: Smith ST
Gender: Men's
Color: Havana Grainy/Suede
Price: $146.25MSRP: $195.00
Rating

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

Nunn Bush - Chase Plain Toe Chukka Contemporary Fashion Boot. Color Brandy. On sale for $59.95. MSRP $90.00.. 4.1 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(8)

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)

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

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

Brown Dockers Norton

Brown Dockers Norton

+3

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

Clarks - Atticus LT Hi. Color Dark Brown Leather. On sale for $116.96. 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: $116.96MSRP: $130.00
Rating

Martin Dingman - Blue Ridge. Color Saddle. Low Stock. On sale for $250.75. MSRP $295.00..

5 left in stock

Brown Martin Dingman Blue Ridge

Brown Martin Dingman Blue Ridge

+2

Brand Name: Martin Dingman
Product Name: Blue Ridge
Gender: Men's
Color: Saddle
Price: $250.75MSRP: $295.00
Rating

Cole Haan - Hawthorne Chukka Boot. Color Dark Chocolate. On sale for $123.68. MSRP $140.00.. 4.4 out of 5 stars

Brown Cole Haan Hawthorne Chukka Boot

Brown Cole Haan Hawthorne Chukka Boot

+3

Brand Name: Cole Haan
Product Name: Hawthorne Chukka Boot
Gender: Men's
Color: Dark Chocolate
Price: $123.68MSRP: $140.00
Rating: 4Rated 4 stars out of 5(9)

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)

TOMS - Travel Lite Moc Chukka. Color Dark Brown. On sale for $85.71. 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: $85.71MSRP: $119.95
Rating

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)

OluKai - Papaku 'Ili. Color Mustang/Mustang. Low Stock. $160.00. 4.2 out of 5 stars

3 left in stock

Brown OluKai Papaku 'Ili

Brown OluKai Papaku 'Ili

+3

Brand Name: OluKai
Product Name: Papaku 'Ili
Gender: Men's
Color: Mustang/Mustang
Price: $160.00
Rating: 4Rated 4 stars out of 5(5)

Clarks - Malwood Top. Color Cola Suede. Low Stock. On sale for $106.48. MSRP $110.00.. 3.0 out of 5 stars

4 left in stock

Brown Clarks Malwood Top

Brown Clarks Malwood Top

+2

Brand Name: Clarks
Product Name: Malwood Top
Gender: Men's
Color: Cola Suede
Price: $106.48MSRP: $110.00
Rating: 3Rated 3 stars out of 5(1)

SOREL - Explorer Next™ Drift Waterproof. Color Tobacco/Sea Salt. On sale for $86.37. 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: $86.37MSRP: $135.00
Rating: 5Rated 5 stars out of 5(16)

SOREL - Carson™ Chukka WP. Color Major/Wet Sand. On sale for $105.00. 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: Major/Wet Sand
Price: $105.00MSRP: $160.00
Rating: 4Rated 4 stars out of 5(11)

Ariat - Clean Country. Color Dark Tan. $119.95. 4.6 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(10)

. 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)

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

Brown Marc Joseph New York Lenox Ave

Brown Marc Joseph New York Lenox Ave

+2

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

Stacy Adams - Kyron Chukka Boot. Color Brown Multi. On sale for $49.45. 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: $49.45MSRP: $115.00
Rating: 4Rated 4 stars out of 5(2)

Marc Joseph New York - Soho Boot. Color Cafe Grainy. On sale for $78.00. 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: $78.00MSRP: $195.00
Rating: 5Rated 5 stars out of 5(1)

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

Brown Nunn Bush Circuit DC Plain Toe Chukka

Brown Nunn Bush Circuit DC Plain Toe Chukka

+3

Brand Name: Nunn Bush
Product Name: Circuit DC Plain Toe Chukka
Gender: Men's
Color: Brown
Price: $59.95MSRP: $85.00
Rating: 4Rated 4 stars out of 5(31)

Nunn Bush - Denali Plain Toe Chukka. Color Brown Crazy Horse. On sale for $89.99. MSRP $115.00.. 4.5 out of 5 stars

Brown Nunn Bush Denali Plain Toe Chukka

Brown Nunn Bush Denali Plain Toe Chukka

+3

Brand Name: Nunn Bush
Product Name: Denali Plain Toe Chukka
Gender: Men's
Color: Brown Crazy Horse
Price: $89.99MSRP: $115.00
Rating: 4Rated 4 stars out of 5(80)

Nunn Bush - Otto Plain Toe Chukka Boot. Color Brown Crazy Horse. On sale for $79.95. MSRP $110.00.. 4.2 out of 5 stars

Brown Nunn Bush Otto Plain Toe Chukka Boot

Brown Nunn Bush Otto Plain Toe Chukka Boot

+4

Brand Name: Nunn Bush
Product Name: Otto Plain Toe Chukka Boot
Gender: Men's
Color: Brown Crazy Horse
Price: $79.95MSRP: $110.00
Rating: 4Rated 4 stars out of 5(14)

TOMS - Navi. Color Water Resistant Topaz Brown Leather. Low Stock. $139.71. 3.9 out of 5 stars

9 left in stock

Brown TOMS Navi

Brown TOMS Navi

+2

Brand Name: TOMS
Product Name: Navi
Gender: Men's
Color: Water Resistant Topaz Brown Leather
Price: $139.71
Rating: 4Rated 4 stars out of 5(26)

Born - Brock. Color Brown Distressed Leather. $140.00. 4.8 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(12)

Stacy Adams - Tilden Chukka Boot. Color Cocoa. On sale for $59.98. MSRP $119.95.. 3.8 out of 5 stars

Brown Stacy Adams Tilden Chukka Boot

Brown Stacy Adams Tilden Chukka Boot

+2

Brand Name: Stacy Adams
Product Name: Tilden Chukka Boot
Gender: Men's
Color: Cocoa
Price: $59.98MSRP: $119.95
Rating: 4Rated 4 stars out of 5(6)

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

Brown Clarks Desert Boot Evo

Brown Clarks Desert Boot Evo

+4

Brand Name: Clarks
Product Name: Desert Boot Evo
Gender: Men's
Color: Dark Brown Suede
Price: $140.00
Rating: 4Rated 4 stars out of 5(13)

Twisted X - MDM0082. Color Mossy Oak® Bottomland® Camo. Low Stock. $124.95.

2 left in stock

Brown Twisted X MDM0082

Brown Twisted X MDM0082

Brand Name: Twisted X
Product Name: MDM0082
Gender: Men's
Color: Mossy Oak® Bottomland® Camo
Price: $124.95
Rating

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(34)

L.L.Bean - Stonington Chukka Boot Leather. Color Deepest Brown. Low Stock. On sale for $99.99. MSRP $139.00.. 4.2 out of 5 stars

1 left in stock

Brown L.L.Bean Stonington Chukka Boot Leather

Brown L.L.Bean Stonington Chukka Boot Leather

Brand Name: L.L.Bean
Product Name: Stonington Chukka Boot Leather
Gender: Men's
Color: Deepest Brown
Price: $99.99MSRP: $139.00
Rating: 4Rated 4 stars out of 5(74)

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)

Clarks - Shacre Boot. Color Dark Sand Suede. On sale for $62.91. MSRP $110.00.. 4.5 out of 5 stars

Brown Clarks Shacre Boot

Brown Clarks Shacre Boot

+4

Brand Name: Clarks
Product Name: Shacre Boot
Gender: Men's
Color: Dark Sand Suede
Price: $62.91MSRP: $110.00
Rating: 4Rated 4 stars out of 5(59)

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

Brown Clarks Wallabee Boot

Brown Clarks Wallabee Boot

+4

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

Clarks - Bushacre 3. Color Dark Brown Leather. On sale for $89.99. MSRP $110.00.. 4.0 out of 5 stars

Brown Clarks Bushacre 3

Brown Clarks Bushacre 3

+6

Brand Name: Clarks
Product Name: Bushacre 3
Gender: Men's
Color: Dark Brown Leather
Price: $89.99MSRP: $110.00
Rating: 4Rated 4 stars out of 5(165)

Florsheim - Lodge Plain Toe Chukka Boot. Color Chestnut Smooth. $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: Chestnut Smooth
Price: $129.95
Rating: 5Rated 5 stars out of 5(107)

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

Brown Clarks Desert Boot

Brown Clarks Desert Boot

+5

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

Twisted X - MDM0080. Color Rubberized Brown. $129.95. 2.0 out of 5 stars

Brown Twisted X MDM0080

Brown Twisted X MDM0080

Brand Name: Twisted X
Product Name: MDM0080
Gender: Men's
Color: Rubberized Brown
Price: $129.95
Rating: 2Rated 2 stars out of 5(1)

Deer Stags - Bangor. Color Redwood/Dark Brown. On sale for $54.99. MSRP $100.00.. 4.1 out of 5 stars

Brown Deer Stags Bangor

Brown Deer Stags Bangor

+2

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(12)

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)

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)

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)

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Brown CH. On sale for $79.95. 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: Brown CH
Price: $79.95MSRP: $115.00
Rating: 4Rated 4 stars out of 5(130)

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)

Rockport - Classic Break Chukka. Color Dark Brown Leather. On sale for $92.79. 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: $92.79MSRP: $139.95
Rating: 4Rated 4 stars out of 5(210)

Steve Madden - Jabbar. Color Dark Tan. On sale for $94.33. MSRP $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: $94.33MSRP: $99.95
Rating: 4Rated 4 stars out of 5(42)

Get on the List

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