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

Men's Chukka Boots

51 items found

Sort By

Your Selections

Search Results

. Clarks - Bushacre 3. Color Sand Waxy Suede. On sale for $96.00. MSRP $110.00.. 4.0 out of 5 stars

Beige Clarks Bushacre 3

Beige Clarks Bushacre 3

+6

Brand Name: Clarks
Product Name: Bushacre 3
Color: Sand Waxy Suede
Price: $96.00MSRP: $110.00
Rating: 4Rated 4 stars out of 5(165)

Stacy Adams - Martfield Chukka Boot. Color Mocha. On sale for $78.41. 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
Color: Mocha
Price: $78.41MSRP: $130.00
Rating: 5Rated 5 stars out of 5(8)

. 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
Color: Tobacco Suede
Price: $90.00
Rating: 4Rated 4 stars out of 5(69)

Clarks - Shacre Boot. Color Dark Sand Suede. On sale for $62.86. 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
Color: Dark Sand Suede
Price: $62.86MSRP: $110.00
Rating: 4Rated 4 stars out of 5(59)

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
Color: Dark Brown
Price: $85.71MSRP: $119.95
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
Color: Dark Brown
Price: $69.99MSRP: $95.00
Rating

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

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
Color: Black Tumbled
Price: $84.95MSRP: $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
Color: Black
Price: $89.95MSRP: $115.00
Rating: 4Rated 4 stars out of 5(79)

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
Color: Cognac Leather
Price: $89.95
Rating: 4Rated 4 stars out of 5(114)

Rockport - Classic Break Chukka. Color Dark Brown Leather. On sale for $99.99. 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
Color: Dark Brown Leather
Price: $99.99MSRP: $139.95
Rating: 4Rated 4 stars out of 5(210)

Nunn Bush - Otto Plain Toe Chukka Boot. Color Black. On sale for $69.95. MSRP $110.00.. 4.2 out of 5 stars

Black Nunn Bush Otto Plain Toe Chukka Boot

Black Nunn Bush Otto Plain Toe Chukka Boot

+4

Brand Name: Nunn Bush
Product Name: Otto Plain Toe Chukka Boot
Color: Black
Price: $69.95MSRP: $110.00
Rating: 4Rated 4 stars out of 5(14)

Johnston & Murphy - Barrett Chukka. Color Tan Full Grain. On sale for $99.97. MSRP $175.00..

Tan Johnston & Murphy Barrett Chukka

Tan Johnston & Murphy Barrett Chukka

Brand Name: Johnston & Murphy
Product Name: Barrett Chukka
Color: Tan Full Grain
Price: $99.97MSRP: $175.00
Rating

Eastland 1955 Edition - Seneca. Color Oak. On sale for $89.95. MSRP $120.00.. 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
Color: Oak
Price: $89.95MSRP: $120.00
Rating: 4Rated 4 stars out of 5(42)

SOREL - Carson™ Chukka WP. Color Blackened Brown/Khaki. On sale for $95.98. 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
Color: Blackened Brown/Khaki
Price: $95.98MSRP: $160.00
Rating: 4Rated 4 stars out of 5(11)

ALDO - Kenora. Color Other Brown. On sale for $96.93. MSRP $130.00.. 5.0 out of 5 stars

Brown ALDO Kenora

Brown ALDO Kenora

+2

Brand Name: ALDO
Product Name: Kenora
Color: Other Brown
Price: $96.93MSRP: $130.00
Rating: 5Rated 5 stars out of 5(2)

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
Color: Black Grainy
Price: $89.95MSRP: $195.00
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
Color: Brown Crazy Horse
Price: $89.95MSRP: $120.00
Rating: 5Rated 5 stars out of 5(33)

Stacy Adams - Maxwell Plain Toe Demi Boot. Color Cognac. On sale for $96.97. 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
Color: Cognac
Price: $96.97MSRP: $125.00
Rating: 5Rated 5 stars out of 5(33)

UGG - Neumel. Color White/White. On sale for $70.48. MSRP $149.95.. 4.8 out of 5 stars

White UGG Neumel

White UGG Neumel

+11

Brand Name: UGG
Product Name: Neumel
Color: White/White
Price: $70.48MSRP: $149.95
Rating: 5Rated 5 stars out of 5(5977)

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
Color: Truffle Washed Grainy
Price: $78.00MSRP: $195.00
Rating: 3Rated 3 stars out of 5(7)

ALDO - Clinton. Color Black. On sale for $92.30. MSRP $130.00..

Black ALDO Clinton

Black ALDO Clinton

+2

Brand Name: ALDO
Product Name: Clinton
Color: Black
Price: $92.30MSRP: $130.00
Rating

Deer Stags - Bangor. Color Black/Black. On sale for $54.99. 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
Color: Black/Black
Price: $54.99MSRP: $100.00
Rating: 4Rated 4 stars out of 5(12)

Steve Madden - Harken - Extended Sizes. Color Black. Low Stock. On sale for $89.95. MSRP $95.00.. 4.1 out of 5 stars

4 left in stock

Black Steve Madden Harken - Extended Sizes

Black Steve Madden Harken - Extended Sizes

+2

Brand Name: Steve Madden
Product Name: Harken - Extended Sizes
Color: Black
Price: $89.95MSRP: $95.00
Rating: 4Rated 4 stars out of 5(115)

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
Color: Brown Multi
Price: $49.45MSRP: $115.00
Rating: 4Rated 4 stars out of 5(2)

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
Color: Woodbury Leather/Dark Roast
Price: $72.00MSRP: $180.00
Rating: 5Rated 5 stars out of 5(418)

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
Color: Black
Price: $59.98MSRP: $119.95
Rating: 4Rated 4 stars out of 5(6)

Marc Joseph New York - Soho Boot. Color Brown Grainy Leather. 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
Color: Brown Grainy Leather
Price: $78.00MSRP: $195.00
Rating: 5Rated 5 stars out of 5(1)

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
Color: Tan Leather
Price: $89.99MSRP: $95.00
Rating: 4Rated 4 stars out of 5(59)

Steve Madden - Jabbar. Color Dark Tan. On sale for $91.77. MSRP $99.95.. 3.9 out of 5 stars

Brown Steve Madden Jabbar

Brown Steve Madden Jabbar

Brand Name: Steve Madden
Product Name: Jabbar
Color: Dark Tan
Price: $91.77MSRP: $99.95
Rating: 4Rated 4 stars out of 5(42)

Thomas & Vine - Keegan. Color Cognac. Low Stock. On sale for $87.93. MSRP $149.99.. 4.0 out of 5 stars

10 left in stock

Tan Thomas & Vine Keegan

Tan Thomas & Vine Keegan

+2

Brand Name: Thomas & Vine
Product Name: Keegan
Color: Cognac
Price: $87.93MSRP: $149.99
Rating: 4Rated 4 stars out of 5(1)

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
Color: Brandy
Price: $59.95MSRP: $90.00
Rating: 4Rated 4 stars out of 5(8)

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

Black Dockers Dartford

Black Dockers Dartford

+3

Brand Name: Dockers
Product Name: Dartford
Color: Black
Price: $49.99MSRP: $85.00
Rating

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

Tan Nunn Bush Circuit DC Plain Toe Chukka

Tan Nunn Bush Circuit DC Plain Toe Chukka

+3

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

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
Color: Tan
Price: $79.96MSRP: $99.95
Rating: 5Rated 5 stars out of 5(7)

hari mari - Adobe Desert Boot. Color Stone. Low Stock. On sale for $85.47. MSRP $150.00.. 3.7 out of 5 stars

1 left in stock

White hari mari Adobe Desert Boot

White hari mari Adobe Desert Boot

+2

Brand Name: hari mari
Product Name: Adobe Desert Boot
Color: Stone
Price: $85.47MSRP: $150.00
Rating: 4Rated 4 stars out of 5(9)

Clarks - Overdale Mid. Color Wheat Nubuck. Low Stock. On sale for $60.51. MSRP $110.00.. 4.4 out of 5 stars

3 left in stock

Tan Clarks Overdale Mid

Tan Clarks Overdale Mid

Brand Name: Clarks
Product Name: Overdale Mid
Color: Wheat Nubuck
Price: $60.51MSRP: $110.00
Rating: 4Rated 4 stars out of 5(14)

SOREL - Explorer Next™ Drift Waterproof. Color Tobacco/Sea Salt. On sale for $87.72. 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
Color: Tobacco/Sea Salt
Price: $87.72MSRP: $135.00
Rating: 5Rated 5 stars out of 5(16)

Vince Camuto - Saveli Casual Boot. Color Eclipse/Cognac. Low Stock. On sale for $89.57. MSRP $169.00..

3 left in stock

Black Vince Camuto Saveli Casual Boot

Black Vince Camuto Saveli Casual Boot

+2

Brand Name: Vince Camuto
Product Name: Saveli Casual Boot
Color: Eclipse/Cognac
Price: $89.57MSRP: $169.00
Rating

Clarks - Morris Peak Waterproof. Color Dark Tan Leather. Low Stock. On sale for $88.40. MSRP $110.00.. 3.4 out of 5 stars

6 left in stock

Brown Clarks Morris Peak Waterproof

Brown Clarks Morris Peak Waterproof

Brand Name: Clarks
Product Name: Morris Peak Waterproof
Color: Dark Tan Leather
Price: $88.40MSRP: $110.00
Rating: 3Rated 3 stars out of 5(26)

Ariat - Clean Country. Color Fudge. Low Stock. On sale for $77.97. MSRP $119.95.. 4.6 out of 5 stars

10 left in stock

Brown Ariat Clean Country

Brown Ariat Clean Country

+2

Brand Name: Ariat
Product Name: Clean Country
Color: Fudge
Price: $77.97MSRP: $119.95
Rating: 5Rated 5 stars out of 5(10)

Clarks - Nature 5 Mid. Color Beeswax Combi. Low Stock. On sale for $98.97. MSRP $150.00..

3 left in stock

Brown Clarks Nature 5 Mid

Brown Clarks Nature 5 Mid

Brand Name: Clarks
Product Name: Nature 5 Mid
Color: Beeswax Combi
Price: $98.97MSRP: $150.00
Rating

Marc Joseph New York - Vestry. Color Brown Napa. Low Stock. On sale for $89.70. MSRP $195.00.. 5.0 out of 5 stars

8 left in stock

Brown Marc Joseph New York Vestry

Brown Marc Joseph New York Vestry

Brand Name: Marc Joseph New York
Product Name: Vestry
Color: Brown Napa
Price: $89.70MSRP: $195.00
Rating: 5Rated 5 stars out of 5(1)

Koolaburra by UGG - Asaiah. Color Chestnut. Low Stock. On sale for $74.58. MSRP $94.99.. 4.0 out of 5 stars

6 left in stock

Brown Koolaburra by UGG Asaiah

Brown Koolaburra by UGG Asaiah

Brand Name: Koolaburra by UGG
Product Name: Asaiah
Color: Chestnut
Price: $74.58MSRP: $94.99
Rating: 4Rated 4 stars out of 5(2)

Stacy Adams - Cai Chukka Boot. Color Black/Gray. Low Stock. $99.95. 4.6 out of 5 stars

1 left in stock

Black Stacy Adams Cai Chukka Boot

Black Stacy Adams Cai Chukka Boot

+2 colors/patterns

Brand Name: Stacy Adams
Product Name: Cai Chukka Boot
Color: Black/Gray
Price: $99.95
Rating: 5Rated 5 stars out of 5(18)

Stacy Adams - Delson Chukka Boot. Color Black Leather. Low Stock. On sale for $71.87. MSRP $105.00.. 4.4 out of 5 stars

8 left in stock

Black Stacy Adams Delson Chukka Boot

Black Stacy Adams Delson Chukka Boot

Brand Name: Stacy Adams
Product Name: Delson Chukka Boot
Color: Black Leather
Price: $71.87MSRP: $105.00
Rating: 4Rated 4 stars out of 5(23)

Johnston & Murphy - Amherst Lug Knit Chukka Boot. Color Navy Knit. Low Stock. On sale for $76.85. MSRP $145.00.. 5.0 out of 5 stars

4 left in stock

Navy Johnston & Murphy Amherst Lug Knit Chukka Boot

Navy Johnston & Murphy Amherst Lug Knit Chukka Boot

+2

Brand Name: Johnston & Murphy
Product Name: Amherst Lug Knit Chukka Boot
Color: Navy Knit
Price: $76.85MSRP: $145.00
Rating: 5Rated 5 stars out of 5(2)

Eastland 1955 Edition - Jack. Color Peanut. On sale for $82.01. MSRP $125.00.. 4.1 out of 5 stars

Brown Eastland 1955 Edition Jack

Brown Eastland 1955 Edition Jack

+2

Brand Name: Eastland 1955 Edition
Product Name: Jack
Color: Peanut
Price: $82.01MSRP: $125.00
Rating: 4Rated 4 stars out of 5(7)

ALDO - Namibi. Color Medium Brown. Low Stock. On sale for $75.40. MSRP $130.00..

4 left in stock

Brown ALDO Namibi

Brown ALDO Namibi

Brand Name: ALDO
Product Name: Namibi
Color: Medium Brown
Price: $75.40MSRP: $130.00
Rating

Stacy Adams - Cosmo Chukka Boot. Color Brown. Low Stock. On sale for $63.92. MSRP $89.95.. 4.7 out of 5 stars

7 left in stock

Brown Stacy Adams Cosmo Chukka Boot

Brown Stacy Adams Cosmo Chukka Boot

Brand Name: Stacy Adams
Product Name: Cosmo Chukka Boot
Color: Brown
Price: $63.92MSRP: $89.95
Rating: 5Rated 5 stars out of 5(30)

Vince Camuto - Leandro. Color Mocca. Low Stock. On sale for $82.76. MSRP $159.00..

2 left in stock

Brown Vince Camuto Leandro

Brown Vince Camuto Leandro

Brand Name: Vince Camuto
Product Name: Leandro
Color: Mocca
Price: $82.76MSRP: $159.00
Rating

Get on the List

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