Skip to main content

The Summer Clearance is here! Enjoy savings up to 40% off thousands of new markdowns - SHOP NOW

Free Gift with Any $39.50 Lancome Purchase - SHOP NOW

Check For In-Store Availability On The Products You Love - LEARN MORE

EARN POINTS WHEN YOU USE YOUR DILLARD’S CREDIT CARD - LEARN MORE

  • Dillard's Logo
  • Back In Stock
  • Sale and Clearance
  • Shop By Brand
  • Limited Availability
  • Credit Card
  • Store LocatorFind a Store
Dillard's The Style of Your Life Homepage
When typing in this field, a list of search results will appear and be automatically updated as you type.
User Login IconLogin
  • Login
  • My Dillard's Account
  • Just For You
  • Order History
  • Returns
  • My Wish List
  • Find a Store
Shopping Bag(0) items in cart
  • Women
  • Juniors
  • Men
  • Kids
  • Shoes
  • Handbags
  • Accessories
  • Lingerie
  • Home
  • Beauty
  • Dillard's Exclusive
  • Just For You
  • Shoes
  • Men's Shoes

chukka boots : Men's Shoes

Just For You
  • Just For You
    (Edit)
Sale
  • Sale

Category

  • Boots
  • Casual Shoes
  • Outdoor
  • Comfort
  • Dress Shoes

Brand

search
Brand
  • Ariat
  • Bed Stu
  • Belvedere
  • Birkenstock
  • Born
  • Eastland
  • Frye
  • Johnston & Murphy
  • Josef Seibel
  • Timberland
  • To Boot New York
  • Twisted X
  • UGG
color
  • Brown
  • Black
  • Tan
  • Grey
  • Green
  • Red
occasion
  • Casual
  • Daytime Occasion
  • Career
  • Outdoor
  • Social/Cocktail/Evening
size
  • 7
  • 7.5
  • 8
  • 8.5
  • 9
  • 9.5
  • 10
  • 10.5
  • 11
  • 11.5
  • 12
  • 13
  • 14
  • 15
  • 17
  • 18
shoe width
  • Medium
  • Wide
  • 28 Items
Twisted X Men's Driving Woven Moccasin Chukka BootsMen's Driving Woven Moccasin Chukka Boots

Twisted XMen's Driving Woven Moccasin Chukka Boots

Rated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 stars(8)
UGG Men's Neumel Classic Fur Lined Suede Lace Up Chukka BootsMen's Neumel Classic Fur Lined Suede Lace Up Chukka Boots

UGGMen's Neumel Classic Fur Lined Suede Lace Up Chukka Boots

Save on Select Items
Orig.
Now
Extended Sizes
Rated 4.84 out of 5 starsRated 4.84 out of 5 starsRated 4.84 out of 5 starsRated 4.84 out of 5 starsRated 4.84 out of 5 stars(6248)
Birkenstock Men's Utti Lace Up ChukkasMen's Utti Lace Up Chukkas

BirkenstockMen's Utti Lace Up Chukkas

Save on Select Items
Orig.
Now
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(4)
Josef Seibel Men's Earl 04 Leather Lace Up Chukka BootsMen's Earl 04 Leather Lace Up Chukka Boots

Josef SeibelMen's Earl 04 Leather Lace Up Chukka Boots

Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(6)
Timberland Men's Redwood Falls Waterproof Leather Chukka BootsMen's Redwood Falls Waterproof Leather Chukka Boots

TimberlandMen's Redwood Falls Waterproof Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.6 out of 5 starsRated 4.6 out of 5 starsRated 4.6 out of 5 starsRated 4.6 out of 5 starsRated 4.6 out of 5 stars(99)
Ariat Men's Lookout Leather Chukka BootsMen's Lookout Leather Chukka Boots

AriatMen's Lookout Leather Chukka Boots

Rated 4.09 out of 5 starsRated 4.09 out of 5 starsRated 4.09 out of 5 starsRated 4.09 out of 5 starsRated 4.09 out of 5 stars(76)
Twisted X Men's Waterproof Chukka Driving MoccasinsMen's Waterproof Chukka Driving Moccasins

Twisted XMen's Waterproof Chukka Driving Moccasins

Internet Exclusive
Extended Sizes
Rated 4.67 out of 5 starsRated 4.67 out of 5 starsRated 4.67 out of 5 starsRated 4.67 out of 5 starsRated 4.67 out of 5 stars(3)
Twisted X Men's Chukka Driving MocsMen's Chukka Driving Mocs

Twisted XMen's Chukka Driving Mocs

Extended Sizes
Men's Driving Woven Moccasin Chukka Boots

PLACEHOLDERMen's Driving Woven Moccasin Chukka Boots

Rated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 stars(8)

TimberlandMen's Maplegrove Chukka Boots

Extended Sizes
Rated 4.63 out of 5 starsRated 4.63 out of 5 starsRated 4.63 out of 5 starsRated 4.63 out of 5 starsRated 4.63 out of 5 stars(148)

UGGMen's Lug Chukka Boots

Extended Sizes
Rated 4.49 out of 5 starsRated 4.49 out of 5 starsRated 4.49 out of 5 starsRated 4.49 out of 5 starsRated 4.49 out of 5 stars(41)

PLACEHOLDERMen's Driving Woven Moccasin Chukka Boots

Rated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 stars(8)

Johnston & MurphyMen's Calder Leather Chukka Lace Up Boots

Save on Select Items
Orig.
Now
Extended Sizes
Rated 4.64 out of 5 starsRated 4.64 out of 5 starsRated 4.64 out of 5 starsRated 4.64 out of 5 starsRated 4.64 out of 5 stars(11)

BornMen's Harrison Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.7 out of 5 starsRated 4.7 out of 5 starsRated 4.7 out of 5 starsRated 4.7 out of 5 starsRated 4.7 out of 5 stars(33)

PLACEHOLDERMen's Driving Woven Moccasin Chukka Boots

Rated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 stars(8)

Twisted XMen's Driving Woven Leather Chukka Moccasins

Extended Sizes
Rated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 starsRated 4.5 out of 5 stars(2)

TimberlandMen's Maple Grove Chukka Boots

Rated 4.63 out of 5 starsRated 4.63 out of 5 starsRated 4.63 out of 5 starsRated 4.63 out of 5 starsRated 4.63 out of 5 stars(148)

PLACEHOLDERMen's Driving Woven Moccasin Chukka Boots

Rated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 starsRated 4.75 out of 5 stars(8)

BelvedereMen's Alvaro Hand Painted Multi Color Ostrich Chukka Boots

Internet Exclusive

Twisted XMen's Chukka Hiker Waterproof Boots

Internet Exclusive
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

To Boot New YorkMen's Vista Chukka Boots

Internet Exclusive
Extended Sizes

Twisted XMen's Driving Leather Chukka Moccasins

Extended Sizes
Rated 4.71 out of 5 starsRated 4.71 out of 5 starsRated 4.71 out of 5 starsRated 4.71 out of 5 starsRated 4.71 out of 5 stars(7)

Twisted XMen's Slip-On Chukka Leather Driving Moccasin Boots

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(2)

Bed StuMen's Clyde Leather Chukka Boots

Internet Exclusive
Extended Sizes

Twisted XMen's Chukka Driving Moccasins

Internet Exclusive
Extended Sizes
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

FryeMen's Astor Leather Chukka Boots

Internet Exclusive

Twisted XMen's Leather Lace-Up Chukka Driving Moccasins

Extended Sizes
Rated 4.67 out of 5 starsRated 4.67 out of 5 starsRated 4.67 out of 5 starsRated 4.67 out of 5 starsRated 4.67 out of 5 stars(3)

EastlandMen's Jack Chukka Boots

Internet Exclusive
Only size 10 available
Rated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 starsRated 5 out of 5 stars(1)

TimberlandMen's Newmarket Chukka Leather Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.8 out of 5 starsRated 4.8 out of 5 starsRated 4.8 out of 5 starsRated 4.8 out of 5 starsRated 4.8 out of 5 stars(15)

TimberlandMen's Westmore Moc-Toe Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.4 out of 5 starsRated 4.4 out of 5 starsRated 4.4 out of 5 starsRated 4.4 out of 5 starsRated 4.4 out of 5 stars(25)

Johnston & MurphyMen's Brody Leather Lace Up Chukka Boots

Permanently Reduced
Orig.
Now
Johnston & Murphy Men's Brody Suede Lace Up Chukka BootsMen's Brody Suede Lace Up Chukka Boots

Johnston & MurphyMen's Brody Suede Lace Up Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Only size 8 available
  • 28 Items

Customer Service

  • Contact Us
  • FAQ, Notices & Policies
  • Product Recalls
  • Returns
  • FAQ, Notices & Policies
  • Product Recalls

Dillard's Credit Card

  • Apply for a Dillard's Card Apply for a Dillard's Card
  • Pay Bill / View Credit Account Opens a simulated dialog
  • Dillard's Cardholder Benefits Dillard's Cardholder Benefits

Contact Us

  • Call 1-817-831-5482
  • Monday-Friday: 7AM-9PM GMT-6
  • Saturday-Sunday: 9AM-7PM GMT-6
  • Contact Us Via Email

More Ways To Shop

  • Registry - Wedding, Baby, and Gift
  • Gift Cards
  • Store Locations
  • Change Country
Stay in Touch.

Sign up for emails and get updates about
new products and the latest trends!

We Are Hiring!
Join our team
Click HERE to learn more
Be a Mobile VIP!

Sign up for texts and be the first to know
about upcoming sales and great offers.

We use certain tools to capture data related to when you open our messages, click on any links or banners it contains, or make purchases.

  • InstagramOpens Dillard's Instagram in a new window
  • FacebookOpens Dillard's Facebook in a new window
  • PintrestOpens Dillard's Pinterest in a new window
  • Twitter/XOpens Dillard's Twitter/X in a new window
  • YouTubeOpens Dillard's YouTube in a new window
  • TikTokOpens Dillard's TikTok in a new window
  • SnapchatOpens Dillard's Snapchat in a new window
  • Site Map
  • Terms Of Use
  • Terms Of Use
  • Dillard's Privacy Policy
  • Dillard's Privacy Policy
  • California Transparency in Supply Chains Act
  • California Transparency in Supply Chains Act
  • Careers
  • Investor Relations
  • About Us

Prices and sale offers may vary by store location, including Dillards.com, and are subject to change. © 2025 Dillard's

***