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

Size 9.5 Chukka Boots

55 items found

Sort By

Your Selections

Search Results

Clarks - Bushacre 3. Color Sand Interest Suede. On sale for $89.99. MSRP $110.00.. 4.0 out of 5 stars

Tan Clarks Bushacre 3

Tan Clarks Bushacre 3

+6

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

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

7 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

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

Marc Joseph New York - Smith ST. Color Black Grainy/Suede. On sale for $169.65. 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: $169.65MSRP: $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

Cole Haan - Originalgrand Chukka Waterproof. Color Navy Blazer Nubuck/Birch Waterproof. Low Stock. On sale for $135.00. MSRP $250.00.. 4.6 out of 5 stars

5 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: $135.00MSRP: $250.00
Rating: 5Rated 5 stars out of 5(28)

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

Black Nunn Bush Chase Plain Toe Chukka Contemporary Fashion Boot

Black 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: Black
Price: $59.95MSRP: $90.00
Rating: 4Rated 4 stars out of 5(9)

Johnston & Murphy Collection - Everson Alpine Boot. Color Tan Italian Calfskin. On sale for $152.75. MSRP $325.00..

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: $152.75MSRP: $325.00
Rating

Martin Dingman - Ernest Kudu. Color Evergreen. Low Stock. On sale for $252.80. 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: $252.80MSRP: $395.00
Rating

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 Brown. 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 Brown
Price: $49.99MSRP: $85.00
Rating: 4Rated 4 stars out of 5(3)

Stacy Adams - Martfield Chukka Boot. Color Sand. On sale for $88.40. MSRP $130.00.. 5.0 out of 5 stars

Beige Stacy Adams Martfield Chukka Boot

Beige Stacy Adams Martfield Chukka Boot

+4

Brand Name: Stacy Adams
Product Name: Martfield Chukka Boot
Gender: Men's
Color: Sand
Price: $88.40MSRP: $130.00
Rating: 5Rated 5 stars out of 5(8)

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

COACH - Suede Chukka Boot. Color Black. On sale for $215.35. 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: $215.35MSRP: $295.00
Rating

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 - Watson. Color Cognac. On sale for $91.00. MSRP $130.00..

Tan ALDO Watson

Tan ALDO Watson

+2

Brand Name: ALDO
Product Name: Watson
Gender: Men's
Color: Cognac
Price: $91.00MSRP: $130.00
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)

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)

ALDO - Kenora. Color Other Brown. On sale for $91.00. 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: $91.00MSRP: $130.00
Rating: 5Rated 5 stars out of 5(2)

TOMS - Travel Lite Moc Chukka. Color Dark Brown. On sale for $80.33. 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: $80.33MSRP: $119.95
Rating

SeaVees - Maslon Desert Boot. Color Natural. On sale for $99.50. MSRP $120.00..

Beige SeaVees Maslon Desert Boot

Beige SeaVees Maslon Desert Boot

Brand Name: SeaVees
Product Name: Maslon Desert Boot
Gender: Men's
Color: Natural
Price: $99.50MSRP: $120.00
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

ECCO - Grainer Chukka Boot. Color Camel. On sale for $129.99. MSRP $190.00.. 4.0 out of 5 stars

Tan ECCO Grainer Chukka Boot

Tan ECCO Grainer Chukka Boot

+2

Brand Name: ECCO
Product Name: Grainer Chukka Boot
Gender: Men's
Color: Camel
Price: $129.99MSRP: $190.00
Rating: 4Rated 4 stars out of 5(1)

johnnie-O - Chill Chukka 2.0. Color Caramel. Low Stock. On sale for $156.18. MSRP $198.00..

1 left in stock

Brown johnnie-O Chill Chukka 2.0

Brown johnnie-O Chill Chukka 2.0

+2

Brand Name: johnnie-O
Product Name: Chill Chukka 2.0
Gender: Men's
Color: Caramel
Price: $156.18MSRP: $198.00
Rating

SOREL - Explorer Next™ Drift Waterproof. Color Tobacco/Sea Salt. On sale for $85.02. 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: $85.02MSRP: $135.00
Rating: 5Rated 5 stars out of 5(16)

Clarks - Desert Boot. Color Dark Grey Suede. On sale for $112.95. MSRP $150.00.. 4.5 out of 5 stars

Gray Clarks Desert Boot

Gray Clarks Desert Boot

+4

Brand Name: Clarks
Product Name: Desert Boot
Gender: Men's
Color: Dark Grey Suede
Price: $112.95MSRP: $150.00
Rating: 4Rated 4 stars out of 5(752)

ALDO - Clinton. Color Dark Brown. On sale for $91.00. MSRP $130.00..

Brown ALDO Clinton

Brown ALDO Clinton

+2

Brand Name: ALDO
Product Name: Clinton
Gender: Men's
Color: Dark Brown
Price: $91.00MSRP: $130.00
Rating

SOREL - Carson™ Chukka WP. Color Major/Wet Sand. On sale for $104.36. 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: $104.36MSRP: $160.00
Rating: 4Rated 4 stars out of 5(11)

Clarks - Corston Wally Waterproof. Color Dark Sand Waxy Suede Warmlined Waterproof. On sale for $107.07. 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: $107.07MSRP: $170.00
Rating: 3Rated 3 stars out of 5(1)

Ariat - Hilo Rancher Moc. Color Tan. On sale for $79.96. 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: $79.96MSRP: $99.95
Rating: 5Rated 5 stars out of 5(7)

Frye - Bowery Chukka. Color Black. On sale for $226.29. 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: $226.29MSRP: $328.00
Rating: 3Rated 3 stars out of 5(11)

Clarks - Desert Coal. Color Stone Suede. On sale for $148.75. MSRP $160.00.. 4.9 out of 5 stars

Gray Clarks Desert Coal

Gray Clarks Desert Coal

+2

Brand Name: Clarks
Product Name: Desert Coal
Gender: Men's
Color: Stone Suede
Price: $148.75MSRP: $160.00
Rating: 5Rated 5 stars out of 5(10)

Sebago - Miwak Aztec. Color Dark Brown/Cognac/Navajo. Low Stock. On sale for $156.00. MSRP $395.00..

5 left in stock

Brown Sebago Miwak Aztec

Brown Sebago Miwak Aztec

Brand Name: Sebago
Product Name: Miwak Aztec
Gender: Men's
Color: Dark Brown/Cognac/Navajo
Price: $156.00MSRP: $395.00
Rating

ALDO - Namibi. Color Medium Brown. Low Stock. On sale for $74.10. MSRP $130.00..

4 left in stock

Brown ALDO Namibi

Brown ALDO Namibi

Brand Name: ALDO
Product Name: Namibi
Gender: Men's
Color: Medium Brown
Price: $74.10MSRP: $130.00
Rating

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)

Marc Joseph New York - Soho Boot. Color Black Grainy Leather. Low Stock. On sale for $115.05. MSRP $195.00.. 5.0 out of 5 stars

8 left in stock

Black Marc Joseph New York Soho Boot

Black Marc Joseph New York Soho Boot

+3

Brand Name: Marc Joseph New York
Product Name: Soho Boot
Gender: Men's
Color: Black Grainy Leather
Price: $115.05MSRP: $195.00
Rating: 5Rated 5 stars out of 5(1)

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)

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)

Stacy Adams - Delson Chukka Boot. Color Camel Nubuck. Low Stock. On sale for $78.75. MSRP $105.00.. 4.4 out of 5 stars

6 left in stock

Taupe Stacy Adams Delson Chukka Boot

Taupe Stacy Adams Delson Chukka Boot

Brand Name: Stacy Adams
Product Name: Delson Chukka Boot
Gender: Men's
Color: Camel Nubuck
Price: $78.75MSRP: $105.00
Rating: 4Rated 4 stars out of 5(23)

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)

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Cognac. On sale for $97.50. 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: $97.50MSRP: $125.00
Rating: 5Rated 5 stars out of 5(34)

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)

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)

TOMS - Navi. Color Water Resistant Topaz Brown Leather. On sale for $122.62. 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: $122.62MSRP: $139.95
Rating: 4Rated 4 stars out of 5(26)

SeaVees - Sun-Tans Chukka. Color Shadow Grey. Low Stock. On sale for $129.00. MSRP $150.00.. 3.0 out of 5 stars

7 left in stock

Gray SeaVees Sun-Tans Chukka

Gray SeaVees Sun-Tans Chukka

Brand Name: SeaVees
Product Name: Sun-Tans Chukka
Gender: Men's
Color: Shadow Grey
Price: $129.00MSRP: $150.00
Rating: 3Rated 3 stars out of 5(9)

Stacy Adams - Tilden Chukka Boot. Color Black. On sale for $59.98. 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: $59.98MSRP: $119.95
Rating: 4Rated 4 stars out of 5(6)

To Boot New York - Dickens. Color Softy Blue 501. Low Stock. On sale for $288.35. MSRP $395.00.. 5.0 out of 5 stars

1 left in stock

Navy To Boot New York Dickens

Navy To Boot New York Dickens

+4

Brand Name: To Boot New York
Product Name: Dickens
Gender: Men's
Color: Softy Blue 501
Price: $288.35MSRP: $395.00
Rating: 5Rated 5 stars out of 5(3)

Florsheim - Norwalk Plain Toe Chukka Boot. Color Cognac Milled Leather. On sale for $101.21. 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: $101.21MSRP: $135.00
Rating: 5Rated 5 stars out of 5(46)

Clarks - Shacre Boot. Color Dark Sand Suede. On sale for $63.01. 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: $63.01MSRP: $110.00
Rating: 4Rated 4 stars out of 5(59)

Clarks - Desert Trek. Color Beeswax. $149.00. 4.5 out of 5 stars

Brown Clarks Desert Trek

Brown Clarks Desert Trek

+4

Brand Name: Clarks
Product Name: Desert Trek
Gender: Men's
Color: Beeswax
Price: $149.00
Rating: 5Rated 5 stars out of 5(102)

Deer Stags - Bangor. Color Black/Black. On sale for $60.00. MSRP $100.00.. 4.1 out of 5 stars

Black Deer Stags Bangor

Black Deer Stags Bangor

+2

Brand Name: Deer Stags
Product Name: Bangor
Gender: Men's
Color: Black/Black
Price: $60.00MSRP: $100.00
Rating: 4Rated 4 stars out of 5(12)

Eastland 1955 Edition - Seneca. Color Tan. Low Stock. On sale for $79.95. MSRP $120.00.. 4.4 out of 5 stars

8 left in stock

Tan Eastland 1955 Edition Seneca

Tan Eastland 1955 Edition Seneca

+3

Brand Name: Eastland 1955 Edition
Product Name: Seneca
Gender: Men's
Color: Tan
Price: $79.95MSRP: $120.00
Rating: 4Rated 4 stars out of 5(42)

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Black Tumbled. On sale for $84.95. 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: $84.95MSRP: $115.00
Rating: 4Rated 4 stars out of 5(130)

Rockport - Classic Break Chukka. Color Dark Brown Leather. On sale for $92.94. 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: $92.94MSRP: $139.95
Rating: 4Rated 4 stars out of 5(210)

Get on the List

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