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

Men's Comfort Chukka Boots

71 items found

Sort By

Your Selections

Search Results

Clarks - Shacre Boot. Color Black Leather. $109.95. 4.5 out of 5 stars

Brand Name: Clarks
Product Name: Shacre Boot
Color: Black Leather
Price: $109.95
Rating: 4Rated 4 stars out of 5(58)

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

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

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

7 left in stock

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

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

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)

Clarks - Corston Wally Waterproof. Color Dark Sand Waxy Suede Warmlined Waterproof. On sale for $79.90. MSRP $170.00.. 3.0 out of 5 stars

Brand Name: Clarks
Product Name: Corston Wally Waterproof
Color: Dark Sand Waxy Suede Warmlined Waterproof
Price: $79.90MSRP: $170.00
Rating: 3Rated 3 stars out of 5(1)

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

Brand Name: UGG
Product Name: Burleigh Chukka
Color: Chestnut
Price: $159.95
Rating: 5Rated 5 stars out of 5(8)

Johnston & Murphy - Barrett Chukka. Color Tan Full Grain. On sale for $92.93. MSRP $175.00..

Brand Name: Johnston & Murphy
Product Name: Barrett Chukka
Color: Tan Full Grain
Price: $92.93MSRP: $175.00
Rating

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

Brand Name: Clarks
Product Name: Bushacre 3
Color: Beeswax Leather
Price: $89.99MSRP: $110.00
Rating: 4Rated 4 stars out of 5(165)

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

Brand Name: Red Wing Heritage
Product Name: Weekend Chukka
Color: Copper Rough & Tough
Price: $249.99
Rating: 4Rated 4 stars out of 5(48)

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

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

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

Brand Name: Florsheim
Product Name: Norwalk Plain Toe Chukka Boot
Color: Black Crazy Horse
Price: $134.95
Rating: 5Rated 5 stars out of 5(44)

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

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

Nunn Bush - Otto Plain Toe Chukka Boot. Color Gray. On sale for $69.95. MSRP $95.00.. 4.7 out of 5 stars

Gray Nunn Bush Otto Plain Toe Chukka Boot

Brand Name: Nunn Bush
Product Name: Otto Plain Toe Chukka Boot
Color: Gray
Price: $69.95MSRP: $95.00
Rating: 5Rated 5 stars out of 5(11)

Born - Brock. Color Brown Distressed Leather. $140.00. 4.8 out of 5 stars

Brand Name: Born
Product Name: Brock
Color: Brown Distressed Leather
Price: $140.00
Rating: 5Rated 5 stars out of 5(12)

Rockport - Classic Break Chukka. Color Dark Brown Leather. On sale for $99.99. MSRP $139.95.. 4.3 out of 5 stars

Brand Name: Rockport
Product Name: Classic Break Chukka
Color: Dark Brown Leather
Price: $99.99MSRP: $139.95
Rating: 4Rated 4 stars out of 5(209)

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

Brand Name: Florsheim
Product Name: Lodge Plain Toe Chukka Boot
Color: Brown Crazy Horse
Price: $129.95
Rating: 5Rated 5 stars out of 5(107)

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

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)

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

Brand Name: Clarks
Product Name: Desert Trek
Color: Beeswax
Price: $150.00
Rating: 5Rated 5 stars out of 5(101)

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

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

Florsheim - Renegade Plain Toe Chukka Boot. Color Black. On sale for $109.95. MSRP $150.00.. 4.3 out of 5 stars

Black Florsheim Renegade Plain Toe Chukka Boot

Brand Name: Florsheim
Product Name: Renegade Plain Toe Chukka Boot
Color: Black
Price: $109.95MSRP: $150.00
Rating: 4Rated 4 stars out of 5(18)

COACH - Spencer Boot. Color Saddle. Low Stock. On sale for $165.20. MSRP $295.00..

9 left in stock

Brand Name: COACH
Product Name: Spencer Boot
Color: Saddle
Price: $165.20MSRP: $295.00
Rating

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

Brand Name: UGG
Product Name: Neumel
Color: White/White
Price: $70.48MSRP: $149.95
Rating: 5Rated 5 stars out of 5(5975)

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

Brand Name: Clarks
Product Name: Atticus LT Hi
Color: Dark Brown Leather
Price: $116.96MSRP: $130.00
Rating

Johnston & Murphy Collection - Everson Alpine Boot. Color Tan Italian Calfskin. On sale for $227.50. MSRP $325.00..

Tan Johnston & Murphy Collection Everson Alpine Boot

Brand Name: Johnston & Murphy Collection
Product Name: Everson Alpine Boot
Color: Tan Italian Calfskin
Price: $227.50MSRP: $325.00
Rating

Martin Dingman - Ernest Kudu. Color Evergreen. Low Stock. On sale for $331.80. MSRP $395.00..

7 left in stock

Brand Name: Martin Dingman
Product Name: Ernest Kudu
Color: Evergreen
Price: $331.80MSRP: $395.00
Rating

OluKai - Papaku 'Ili. Color Tan/Tan. $160.00. 4.2 out of 5 stars

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

BOSS - Calev Desert Boot. Color Dark Brown. On sale for $181.70. MSRP $230.00..

Brand Name: BOSS
Product Name: Calev Desert Boot
Color: Dark Brown
Price: $181.70MSRP: $230.00
Rating

COACH - Suede Chukka Boot. Color Black. On sale for $209.45. MSRP $295.00..

Brand Name: COACH
Product Name: Suede Chukka Boot
Color: Black
Price: $209.45MSRP: $295.00
Rating

Barbour - Barbour Readhead. Color Black. Low Stock. $220.00.

9 left in stock

Brand Name: Barbour
Product Name: Barbour Readhead
Color: Black
Price: $220.00
Rating

Sperry - A/O Plushwave Lug Chukka. Color Black 2. $139.95. 4.2 out of 5 stars

Brand Name: Sperry
Product Name: A/O Plushwave Lug Chukka
Color: Black 2
Price: $139.95
Rating: 4Rated 4 stars out of 5(25)

Johnston & Murphy - Upton Chukka Boot. Color Tan Full Grain. $169.00.

Brand Name: Johnston & Murphy
Product Name: Upton Chukka Boot
Color: Tan Full Grain
Price: $169.00
Rating

Nunn Bush - Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology. Color Tan 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

Brand Name: Nunn Bush
Product Name: Ozark Plain Toe Chukka Boot with KORE Walking Comfort Technology
Color: Tan CH
Price: $79.95MSRP: $115.00
Rating: 4Rated 4 stars out of 5(129)

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

Brand Name: Deer Stags
Product Name: Bangor
Color: Redwood/Dark Brown
Price: $54.99MSRP: $100.00
Rating: 4Rated 4 stars out of 5(12)

ALDO - Watson. Color Cognac. On sale for $93.45. MSRP $130.00..

Brand Name: ALDO
Product Name: Watson
Color: Cognac
Price: $93.45MSRP: $130.00
Rating

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

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

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

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

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

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

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

Brand Name: Nunn Bush
Product Name: Circuit DC Plain Toe Chukka
Color: Brown
Price: $59.95MSRP: $85.00
Rating: 4Rated 4 stars out of 5(29)

Clarks - Desert Coal. Color Stone Suede. $160.00. 4.9 out of 5 stars

Brand Name: Clarks
Product Name: Desert Coal
Color: Stone Suede
Price: $160.00
Rating: 5Rated 5 stars out of 5(10)

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

Brand Name: Clarks
Product Name: Desert Boot Evo
Color: Black Suede
Price: $140.00
Rating: 4Rated 4 stars out of 5(13)

Stacy Adams - Martfield Chukka Boot. Color Dark Gray. On sale for $78.24. MSRP $130.00.. 5.0 out of 5 stars

Brand Name: Stacy Adams
Product Name: Martfield Chukka Boot
Color: Dark Gray
Price: $78.24MSRP: $130.00
Rating: 5Rated 5 stars out of 5(8)

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

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

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

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

Eastland 1955 Edition - Jack. Color Peanut. Low Stock. On sale for $80.54. MSRP $125.00.. 4.1 out of 5 stars

6 left in stock

Brand Name: Eastland 1955 Edition
Product Name: Jack
Color: Peanut
Price: $80.54MSRP: $125.00
Rating: 4Rated 4 stars out of 5(7)

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

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

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

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

Minnetonka - Torrey. Color Charcoal. $74.95.

Brand Name: Minnetonka
Product Name: Torrey
Color: Charcoal
Price: $74.95
Rating

Johnston & Murphy - McGuffey Lug Chukka Boot. Color Brown Waterproof Full Grain. Low Stock. On sale for $119.99. MSRP $155.00.. 3.0 out of 5 stars

1 left in stock

Red Johnston & Murphy McGuffey Lug Chukka Boot

Brand Name: Johnston & Murphy
Product Name: McGuffey Lug Chukka Boot
Color: Brown Waterproof Full Grain
Price: $119.99MSRP: $155.00
Rating: 3Rated 3 stars out of 5(1)

Clarks - Morris Peak Waterproof. Color Dark Tan Leather. Low Stock. On sale for $91.00. MSRP $110.00.. 3.4 out of 5 stars

8 left in stock

Brand Name: Clarks
Product Name: Morris Peak Waterproof
Color: Dark Tan Leather
Price: $91.00MSRP: $110.00
Rating: 3Rated 3 stars out of 5(26)

ECCO - Turn GORE-TEX® Chukka Tie. Color Black. Low Stock. On sale for $146.62. MSRP $230.00.. 4.3 out of 5 stars

4 left in stock

Brand Name: ECCO
Product Name: Turn GORE-TEX® Chukka Tie
Color: Black
Price: $146.62MSRP: $230.00
Rating: 4Rated 4 stars out of 5(62)

Timberland - Redwood Falls Waterproof Chukka. Color Medium Brown Full Grain 1. Low Stock. On sale for $98.00. MSRP $130.00.. 4.6 out of 5 stars

1 left in stock

Brown Timberland Redwood Falls Waterproof Chukka

Brand Name: Timberland
Product Name: Redwood Falls Waterproof Chukka
Color: Medium Brown Full Grain 1
Price: $98.00MSRP: $130.00
Rating: 5Rated 5 stars out of 5(106)

ECCO - St.1 Hybrid Boot GTX. Color Navajo Brown Cow Oil Nubuck. Low Stock. On sale for $194.89. MSRP $270.00.. 4.2 out of 5 stars

2 left in stock

Brand Name: ECCO
Product Name: St.1 Hybrid Boot GTX
Color: Navajo Brown Cow Oil Nubuck
Price: $194.89MSRP: $270.00
Rating: 4Rated 4 stars out of 5(20)

Clarks - Whiddon Mid. Color Waterproof Black Leather. Low Stock. $109.95. 3.5 out of 5 stars

4 left in stock

Brand Name: Clarks
Product Name: Whiddon Mid
Color: Waterproof Black Leather
Price: $109.95
Rating: 4Rated 4 stars out of 5(8)

Hey Dude - Bradley Leather Boot. Color Black. Low Stock. On sale for $56.98. MSRP $94.99.. 4.3 out of 5 stars

7 left in stock

Brand Name: Hey Dude
Product Name: Bradley Leather Boot
Color: Black
Price: $56.98MSRP: $94.99
Rating: 4Rated 4 stars out of 5(146)

Clarks - Oakpark Mid. Color Tan Tumbled Leather. On sale for $91.00. MSRP $110.00.. 5.0 out of 5 stars

Brand Name: Clarks
Product Name: Oakpark Mid
Color: Tan Tumbled Leather
Price: $91.00MSRP: $110.00
Rating: 5Rated 5 stars out of 5(1)

Magnanni - Maren. Color Tobacco 1. Low Stock. On sale for $297.50. MSRP $425.00..

2 left in stock

Brand Name: Magnanni
Product Name: Maren
Color: Tobacco 1
Price: $297.50MSRP: $425.00
Rating

Clarks - Nature 5 Mid. Color Beeswax Combi. Low Stock. On sale for $100.47. MSRP $150.00..

3 left in stock

Brand Name: Clarks
Product Name: Nature 5 Mid
Color: Beeswax Combi
Price: $100.47MSRP: $150.00
Rating

Allen Edmonds - Harris. Color Brown Leather. Low Stock. $395.00.

4 left in stock

Brand Name: Allen Edmonds
Product Name: Harris
Color: Brown Leather
Price: $395.00
Rating

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

7 left in stock

Brand Name: Allen Edmonds
Product Name: Chandler
Color: Loden
Price: $475.00
Rating: 4Rated 4 stars out of 5(60)

Propet - Findley. Color Tan. Low Stock. $114.95. 3.5 out of 5 stars

3 left in stock

Brand Name: Propet
Product Name: Findley
Color: Tan
Price: $114.95
Rating: 3Rated 3 stars out of 5(11)

PIKOLINOS - Avila M1T-8011C1. Color Black. Low Stock. $210.00.

1 left in stock

Brand Name: PIKOLINOS
Product Name: Avila M1T-8011C1
Color: Black
Price: $210.00
Rating

Naot - General. Color Black Water Resistant Leather. Low Stock. $229.95. 4.2 out of 5 stars

7 left in stock

Brand Name: Naot
Product Name: General
Color: Black Water Resistant Leather
Price: $229.95
Rating: 4Rated 4 stars out of 5(12)

johnnie-O - Chill Chukka 2.0. Color Caramel. Low Stock. On sale for $168.10. MSRP $198.00..

1 left in stock

Brand Name: johnnie-O
Product Name: Chill Chukka 2.0
Color: Caramel
Price: $168.10MSRP: $198.00
Rating

Carlos by Carlos Santana - Corazon Chukka Boot. Color Black Full Grain Calfskin Leather. Low Stock. On sale for $111.30. MSRP $153.95.. 4.2 out of 5 stars

2 left in stock

Black Carlos by Carlos Santana Corazon Chukka Boot

Brand Name: Carlos by Carlos Santana
Product Name: Corazon Chukka Boot
Color: Black Full Grain Calfskin Leather
Price: $111.30MSRP: $153.95
Rating: 4Rated 4 stars out of 5(26)

BOSS - Calev Leather Desert Boot. Color Dark Brown. Low Stock. $230.00.

8 left in stock

Brand Name: BOSS
Product Name: Calev Leather Desert Boot
Color: Dark Brown
Price: $230.00
Rating

PIKOLINOS - Berna M8J-8181. Color Olmo. Low Stock. $200.00. 5.0 out of 5 stars

2 left in stock

Brand Name: PIKOLINOS
Product Name: Berna M8J-8181
Color: Olmo
Price: $200.00
Rating: 5Rated 5 stars out of 5(3)

Johnston & Murphy - Amherst Lug Knit Chukka Boot. Color Grey. $145.00. 5.0 out of 5 stars

Gray Johnston & Murphy Amherst Lug Knit Chukka Boot

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

Clarks - Malwood Top. Color Cola Suede. Low Stock. On sale for $92.54. MSRP $110.00.. 3.0 out of 5 stars

6 left in stock

Brand Name: Clarks
Product Name: Malwood Top
Color: Cola Suede
Price: $92.54MSRP: $110.00
Rating: 3Rated 3 stars out of 5(1)

Palladium - Pallasider Mid Cuff. Color Apple Cinnamon. Low Stock. On sale for $84.80. MSRP $160.00..

4 left in stock

Brand Name: Palladium
Product Name: Pallasider Mid Cuff
Color: Apple Cinnamon
Price: $84.80MSRP: $160.00
Rating

UGG - Neumel FT. Color Sea Salt Leather. Low Stock. On sale for $111.99. MSRP $159.95.. 4.2 out of 5 stars

9 left in stock

Brand Name: UGG
Product Name: Neumel FT
Color: Sea Salt Leather
Price: $111.99MSRP: $159.95
Rating: 4Rated 4 stars out of 5(8)

Clarks - Overdale Mid. Color Wheat Nubuck. Low Stock. On sale for $74.67. MSRP $110.00.. 4.4 out of 5 stars

3 left in stock

Brand Name: Clarks
Product Name: Overdale Mid
Color: Wheat Nubuck
Price: $74.67MSRP: $110.00
Rating: 4Rated 4 stars out of 5(14)

Men's Comfort Chukka Boots

Your Selections

Search Results

Get on the List

About Zappos

Customer Service

Resources

Explore Zappos