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

Size 7.5 Leather Chukka Boots

54 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(753)

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

Brown Clarks Wallabee Boot

Brown Clarks Wallabee Boot

+5

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

Ariat - Lookout. Color Earth/Stone Suede. $149.95. 4.2 out of 5 stars

Brown Ariat Lookout

Brown Ariat Lookout

Brand Name: Ariat
Product Name: Lookout
Gender: Men's
Color: Earth/Stone Suede
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 $227.15. 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: $227.15MSRP: $295.00
Rating

ECCO - Grainer Chukka Boot. Color Black. On sale for $169.10. 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: $169.10MSRP: $190.00
Rating: 4Rated 4 stars out of 5(1)

. Florsheim - Vibe Plain Toe Chukka. Color Brown Crazy Horse. $124.95.

Brown Florsheim Vibe Plain Toe Chukka

Brown Florsheim Vibe Plain Toe Chukka

+2

Brand Name: Florsheim
Product Name: Vibe Plain Toe Chukka
Gender: Men's
Color: Brown Crazy Horse
Price: $124.95
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)

ALDO - Kenora. Color Other Brown. On sale for $97.49. 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: $97.49MSRP: $130.00
Rating: 5Rated 5 stars out of 5(2)

ALDO - Clinton. Color Dark Brown. On sale for $106.74. MSRP $130.00..

Brown ALDO Clinton

Brown ALDO Clinton

+2

Brand Name: ALDO
Product Name: Clinton
Gender: Men's
Color: Dark Brown
Price: $106.74MSRP: $130.00
Rating

. Florsheim - Renegade Plain Toe Chukka Boot. Color Brown Crazy Horse. $149.95. 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 Crazy Horse
Price: $149.95
Rating: 4Rated 4 stars out of 5(18)

. 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)

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

Brown Clarks Bushacre 3

Brown Clarks Bushacre 3

+7

Brand Name: Clarks
Product Name: Bushacre 3
Gender: Men's
Color: Beeswax Leather
Price: $89.99MSRP: $110.00
Rating: 4Rated 4 stars out of 5(166)

. Steve Madden - Hestonn. Color Dark Taupe. On sale for $63.00. MSRP $90.00.. 3.8 out of 5 stars

Taupe Steve Madden Hestonn

Taupe Steve Madden Hestonn

+3

Brand Name: Steve Madden
Product Name: Hestonn
Gender: Men's
Color: Dark Taupe
Price: $63.00MSRP: $90.00
Rating: 4Rated 4 stars out of 5(69)

TOMS - Navi. Color Water Resistant Topaz Brown Leather. On sale for $134.71. 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: $134.71MSRP: $139.95
Rating: 4Rated 4 stars out of 5(27)

SOREL - Carson™ Chukka WP. Color Blackened Brown/Khaki. On sale for $101.74. MSRP $160.00.. 3.8 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: Blackened Brown/Khaki
Price: $101.74MSRP: $160.00
Rating: 4Rated 4 stars out of 5(12)

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)

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)

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)

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)

Nunn Bush - Otto Plain Toe Chukka Boot. Color Navy. On sale for $64.95. MSRP $95.00.. 4.3 out of 5 stars

Navy Nunn Bush Otto Plain Toe Chukka Boot

Navy Nunn Bush Otto Plain Toe Chukka Boot

+4

Brand Name: Nunn Bush
Product Name: Otto Plain Toe Chukka Boot
Gender: Men's
Color: Navy
Price: $64.95MSRP: $95.00
Rating: 4Rated 4 stars out of 5(15)

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(34)

Florsheim - Norwalk Plain Toe Chukka Boot. Color Black Crazy Horse. $134.95. 4.6 out of 5 stars

Black Florsheim Norwalk Plain Toe Chukka Boot

Black Florsheim Norwalk Plain Toe Chukka Boot

Brand Name: Florsheim
Product Name: Norwalk Plain Toe Chukka Boot
Gender: Men's
Color: Black Crazy Horse
Price: $134.95
Rating: 5Rated 5 stars out of 5(46)

Cole Haan - Original Grand Chukka. Color Woodbury Leather/Ivory. On sale for $89.97. MSRP $180.00.. 4.6 out of 5 stars

Burgundy Cole Haan Original Grand Chukka

Burgundy Cole Haan Original Grand Chukka

+2

Brand Name: Cole Haan
Product Name: Original Grand Chukka
Gender: Men's
Color: Woodbury Leather/Ivory
Price: $89.97MSRP: $180.00
Rating: 5Rated 5 stars out of 5(426)

Stacy Adams - Kyron Chukka Boot. Color Brown Multi. On sale for $51.75. 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: $51.75MSRP: $115.00
Rating: 4Rated 4 stars out of 5(2)

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)

Twisted X - MDM0019. Color Bomber/Neon Orange. On sale for $103.96. MSRP $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: $103.96MSRP: $129.95
Rating: 5Rated 5 stars out of 5(7)

ECCO - Turn GORE-TEX® Chukka Tie. Color Black. Low Stock. $229.95. 4.3 out of 5 stars

5 left in stock

Black ECCO Turn GORE-TEX® Chukka Tie

Black ECCO Turn GORE-TEX® Chukka Tie

+2

Brand Name: ECCO
Product Name: Turn GORE-TEX® Chukka Tie
Gender: Men's
Color: Black
Price: $229.95
Rating: 4Rated 4 stars out of 5(62)

Twisted X - MDM0049. Color Bomber. On sale for $103.96. MSRP $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: $103.96MSRP: $129.95
Rating: 4Rated 4 stars out of 5(4)

Clarks - Shacre Boot. Color Beeswax Leather. On sale for $72.00. MSRP $110.00.. 4.5 out of 5 stars

Brown Clarks Shacre Boot

Brown Clarks Shacre Boot

+5

Brand Name: Clarks
Product Name: Shacre Boot
Gender: Men's
Color: Beeswax Leather
Price: $72.00MSRP: $110.00
Rating: 4Rated 4 stars out of 5(60)

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)

Twisted X Work - MDMW001. Color Brown. Low Stock. On sale for $119.96. MSRP $149.95.. 4.1 out of 5 stars

8 left in stock

Brown Twisted X Work MDMW001

Brown Twisted X Work MDMW001

Brand Name: Twisted X Work
Product Name: MDMW001
Gender: Men's
Color: Brown
Price: $119.96MSRP: $149.95
Rating: 4Rated 4 stars out of 5(8)

PIKOLINOS - York M2M-8027. Color Cuero. Low Stock. On sale for $121.00. MSRP $220.00..

2 left in stock

Tan PIKOLINOS York M2M-8027

Tan PIKOLINOS York M2M-8027

Brand Name: PIKOLINOS
Product Name: York M2M-8027
Gender: Men's
Color: Cuero
Price: $121.00MSRP: $220.00
Rating

Roper - Clearcut. Color Brown Vintage Leather. Low Stock. On sale for $104.55. MSRP $110.99.. 4.8 out of 5 stars

5 left in stock

Mahogany Roper Clearcut

Mahogany Roper Clearcut

Brand Name: Roper
Product Name: Clearcut
Gender: Men's
Color: Brown Vintage Leather
Price: $104.55MSRP: $110.99
Rating: 5Rated 5 stars out of 5(12)

Eastland 1955 Edition - Seneca. Color Bomber Brown. On sale for $84.95. MSRP $110.00.. 4.4 out of 5 stars

Brown Eastland 1955 Edition Seneca

Brown Eastland 1955 Edition Seneca

+3

Brand Name: Eastland 1955 Edition
Product Name: Seneca
Gender: Men's
Color: Bomber Brown
Price: $84.95MSRP: $110.00
Rating: 4Rated 4 stars out of 5(42)

Stacy Adams - Delson Chukka Boot. Color Black Leather. Low Stock. On sale for $72.02. MSRP $105.00.. 4.4 out of 5 stars

9 left in stock

Black Stacy Adams Delson Chukka Boot

Black Stacy Adams Delson Chukka Boot

Brand Name: Stacy Adams
Product Name: Delson Chukka Boot
Gender: Men's
Color: Black Leather
Price: $72.02MSRP: $105.00
Rating: 4Rated 4 stars out of 5(23)

Massimo Matteo - Chukka Classic Boots. Color Havana Leather. Low Stock. On sale for $71.21. MSRP $94.95.. 5.0 out of 5 stars

8 left in stock

Pewter Massimo Matteo Chukka Classic Boots

Pewter Massimo Matteo Chukka Classic Boots

Brand Name: Massimo Matteo
Product Name: Chukka Classic Boots
Gender: Men's
Color: Havana Leather
Price: $71.21MSRP: $94.95
Rating: 5Rated 5 stars out of 5(1)

Clarks - Morris Peak Waterproof. Color Dark Tan Leather. Low Stock. On sale for $78.00. MSRP $110.00.. 3.5 out of 5 stars

3 left in stock

Brown Clarks Morris Peak Waterproof

Brown Clarks Morris Peak Waterproof

Brand Name: Clarks
Product Name: Morris Peak Waterproof
Gender: Men's
Color: Dark Tan Leather
Price: $78.00MSRP: $110.00
Rating: 3Rated 3 stars out of 5(27)

La Canadienne - Alston. Color Taupe Suede. On sale for $246.50. 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: $246.50MSRP: $425.00
Rating

Allen Edmonds - Chandler. Color Light Brown. Low Stock. $475.00. 4.4 out of 5 stars

3 left in stock

Tan Allen Edmonds Chandler

Tan Allen Edmonds Chandler

+5

Brand Name: Allen Edmonds
Product Name: Chandler
Gender: Men's
Color: Light Brown
Price: $475.00
Rating: 4Rated 4 stars out of 5(63)

Roper - Performance 2-Eyelet Ankle Boot. Color Brown Ostrich. Low Stock. On sale for $111.04. MSRP $126.99.. 4.6 out of 5 stars

4 left in stock

Brown Roper Performance 2-Eyelet Ankle Boot

Brown Roper Performance 2-Eyelet Ankle Boot

Brand Name: Roper
Product Name: Performance 2-Eyelet Ankle Boot
Gender: Men's
Color: Brown Ostrich
Price: $111.04MSRP: $126.99
Rating: 5Rated 5 stars out of 5(7)

Stacy Adams - Tilden Chukka Boot. Color Navy. Low Stock. On sale for $49.98. MSRP $119.95.. 3.8 out of 5 stars

1 left in stock

Navy Stacy Adams Tilden Chukka Boot

Navy Stacy Adams Tilden Chukka Boot

+3

Brand Name: Stacy Adams
Product Name: Tilden Chukka Boot
Gender: Men's
Color: Navy
Price: $49.98MSRP: $119.95
Rating: 4Rated 4 stars out of 5(6)

Stacy Adams - Cai Chukka Boot. Color Brown. Low Stock. On sale for $71.96. MSRP $99.95.. 4.6 out of 5 stars

3 left in stock

Brown Stacy Adams Cai Chukka Boot

Brown Stacy Adams Cai Chukka Boot

+2 colors/patterns

Brand Name: Stacy Adams
Product Name: Cai Chukka Boot
Gender: Men's
Color: Brown
Price: $71.96MSRP: $99.95
Rating: 5Rated 5 stars out of 5(18)

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)

Steve Madden - Jabbar. Color Dark Tan. On sale for $85.43. 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: $85.43MSRP: $99.95
Rating: 4Rated 4 stars out of 5(42)

Twisted X - MDM0057. Color Oiled Saddle/Midnight. On sale for $108.76. MSRP $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: $108.76MSRP: $135.95
Rating: 5Rated 5 stars out of 5(3)

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)

Twisted X - MDM0014. Color Copper. On sale for $103.96. MSRP $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: $103.96MSRP: $129.95
Rating: 5Rated 5 stars out of 5(5)

Twisted X - MDM0016. Color Black. Low Stock. On sale for $103.96. MSRP $129.95.. 4.3 out of 5 stars

9 left in stock

Black Twisted X MDM0016

Black Twisted X MDM0016

Brand Name: Twisted X
Product Name: MDM0016
Gender: Men's
Color: Black
Price: $103.96MSRP: $129.95
Rating: 4Rated 4 stars out of 5(7)

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Black Tumbled. On sale for $79.99. MSRP $115.00.. 4.3 out of 5 stars

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

Black 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: Black Tumbled
Price: $79.99MSRP: $115.00
Rating: 4Rated 4 stars out of 5(130)

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Cognac. On sale for $90.79. 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: $90.79MSRP: $125.00
Rating: 5Rated 5 stars out of 5(34)

ALDO - Watson. Color Black. Low Stock. On sale for $107.90. MSRP $130.00..

6 left in stock

Black ALDO Watson

Black ALDO Watson

+2

Brand Name: ALDO
Product Name: Watson
Gender: Men's
Color: Black
Price: $107.90MSRP: $130.00
Rating

Bruno Magli - Taddeo. Color Taupe Suede. Low Stock. On sale for $285.00. MSRP $375.00..

4 left in stock

Taupe Bruno Magli Taddeo

Taupe Bruno Magli Taddeo

+2

Brand Name: Bruno Magli
Product Name: Taddeo
Gender: Men's
Color: Taupe Suede
Price: $285.00MSRP: $375.00
Rating

PIKOLINOS - Berna M8J-8181. Color Olmo. Low Stock. $200.00. 4.5 out of 5 stars

2 left in stock

Brown PIKOLINOS Berna M8J-8181

Brown PIKOLINOS Berna M8J-8181

+2

Brand Name: PIKOLINOS
Product Name: Berna M8J-8181
Gender: Men's
Color: Olmo
Price: $200.00
Rating: 5Rated 5 stars out of 5(4)

Get on the List

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