Skip to main content

Incredible Deals on Thousands of New Markdowns Up to 33%-40% off! - SHOP NOW

iPhone Update & Can't Find Our Emails in Your Inbox? - CLICK HERE

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

chukka boots : Shoes

Sale
  • Sale

Category

  • Men's Shoes
  • Women's Shoes
  • Kids' Shoes

Brand

search
Brand
  • Ariat
  • Bed Stu
  • Belvedere
  • Birkenstock
  • Born
  • Clarks
  • Cole Haan
  • Danner
  • Dr. Martens
  • ECCO
  • Flag LTD.
  • Frye
  • Johnston & Murphy
  • Josef Seibel
  • L.L.Bean
  • Polo Ralph Lauren
  • Ryka
  • Sorel
  • Steve Madden
  • Timberland
  • To Boot New York
  • Twisted X
  • UGG
color
  • Brown
  • Black
  • Tan
  • Grey
  • Green
  • Red
  • Ivory
  • All
  • Men's Shoes
  • Women's Shoes
  • Kids' Shoes
  • 67 Items
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

Extended Sizes
Rated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 stars(354)
Born Analia Distressed Suede Ankle Chukka BootiesAnalia Distressed Suede Ankle Chukka Booties

BornAnalia Distressed Suede Ankle Chukka Booties

Save on Select Items
Orig.
Now
Extended Sizes
Rated 4.4286 out of 5 starsRated 4.4286 out of 5 starsRated 4.4286 out of 5 starsRated 4.4286 out of 5 starsRated 4.4286 out of 5 stars(14)
Johnston & Murphy Men's Calder Leather Chukka Lace Up BootsMen's Calder Leather Chukka Lace Up Boots

Johnston & MurphyMen's Calder Leather Chukka Lace Up Boots

Extended Sizes
Rated 4.5094 out of 5 starsRated 4.5094 out of 5 starsRated 4.5094 out of 5 starsRated 4.5094 out of 5 starsRated 4.5094 out of 5 stars(53)
Johnston & Murphy Boys' Calder Leather Lace Up Chukka Boots (Youth)Boys' Calder Leather Lace Up Chukka Boots (Youth)

Johnston & MurphyBoys' Calder Leather Lace Up Chukka Boots (Youth)

Ariat Men's Split Rock Leather Moc Toe Chukka BootsMen's Split Rock Leather Moc Toe Chukka Boots

AriatMen's Split Rock Leather Moc Toe 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(1)
Twisted X Men's Driving CellStretch Leather Moc Toe Chukka BootsMen's Driving CellStretch Leather Moc Toe Chukka Boots

Twisted XMen's Driving CellStretch Leather Moc Toe Chukka Boots

Extended Sizes
Rated 2 out of 5 starsRated 2 out of 5 starsRated 2 out of 5 starsRated 2 out of 5 starsRated 2 out of 5 stars(1)
Twisted X Men's Driving Leather Moccasin Chukka BootsMen's Driving Leather Moccasin Chukka Boots

Twisted XMen's Driving Leather Moccasin 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(8)
Cole Haan Men's Morse Leather Chukka BootsMen's Morse Leather Chukka Boots

Cole HaanMen's Morse Leather Chukka Boots

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

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

Extended Sizes
Rated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 stars(354)

Twisted XMen's Driving Leather Moc Toe Chukka Boots

Extended Sizes

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)

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

Extended Sizes
Rated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 stars(354)

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

DannerWomen's Inquire Chukka Waterproof Leather Hiking Boots

Extended Sizes

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

Extended Sizes
Rated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 stars(354)

Twisted XWomen's Printed Leather Driving Moc Toe Chukka 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)

DannerWomen's Inquire Chukka Waterproof Suede Hiking Boots

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

Extended Sizes
Rated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 starsRated 4.8814 out of 5 stars(354)

Twisted XMen's Driving Moccasin Chukka Boots

Internet Exclusive
Extended Sizes

ClarksOriginal Wallabee Suede Chukka Booties

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)

Johnston & MurphyBoys' Calder Leather Hook-and-Loop Chukka Boots (Infant)

Twisted XWomen's Original Leather Driving Moc Toe Chukka Boots

Extended Sizes
Rated 4.5882 out of 5 starsRated 4.5882 out of 5 starsRated 4.5882 out of 5 starsRated 4.5882 out of 5 starsRated 4.5882 out of 5 stars(17)

Twisted XWomen's Tooled Moc Toe Driving Chukka Booties

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(8)

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)

Cole HaanMen's Chamberlin Water Resistant Nubuck Chukka Boots

Internet Exclusive

BirkenstockMen's Utti Lace Up Chukkas

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)

L.L.BeanMen's Allagash Handsewn Leather Chukka Boots

Rated 3.9167 out of 5 starsRated 3.9167 out of 5 starsRated 3.9167 out of 5 starsRated 3.9167 out of 5 starsRated 3.9167 out of 5 stars(36)

RykaWomen's Vibrant Washable Chukka Platform Ankle Booties

Extended Sizes
Rated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 starsRated 3.5 out of 5 stars(2)

TimberlandWomen's Rowan Way Warm-Lined Water-Resistant Winter Chukka Booties

Internet Exclusive
Extended Sizes
Only size 6, 6.5 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(7)

AriatMen's Lookout Leather Chukka Boots

Only size 11 available
Rated 4.1324 out of 5 starsRated 4.1324 out of 5 starsRated 4.1324 out of 5 starsRated 4.1324 out of 5 starsRated 4.1324 out of 5 stars(68)

FryeMen's Paul Leather Chukka 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(2)

SorelMen's Madson II Waterproof Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.375 out of 5 starsRated 4.375 out of 5 starsRated 4.375 out of 5 starsRated 4.375 out of 5 starsRated 4.375 out of 5 stars(88)

AriatMen's Clean Country Suede Chukka Boots

Rated 4.381 out of 5 starsRated 4.381 out of 5 starsRated 4.381 out of 5 starsRated 4.381 out of 5 starsRated 4.381 out of 5 stars(21)

SorelMen's Slabtown 62' Stoic Suede Chukka 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(1)

TimberlandMen's Redwood Falls Waterproof Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.3582 out of 5 starsRated 4.3582 out of 5 starsRated 4.3582 out of 5 starsRated 4.3582 out of 5 starsRated 4.3582 out of 5 stars(67)

TimberlandWomen's Stone Street Mid Lace Up Waterproof Chukka Booties

Internet Exclusive
Extended Sizes
Rated 4.7273 out of 5 starsRated 4.7273 out of 5 starsRated 4.7273 out of 5 starsRated 4.7273 out of 5 starsRated 4.7273 out of 5 stars(11)

L.L.BeanMen's Eco Bay Nubuck 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(1)

Twisted XMen's Chukka Hiker Waterproof 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(1)

BelvedereMen's Alvaro Hand Painted Multi Color Ostrich Chukka Boots

Internet Exclusive

Twisted XMen's Waterproof Driving Moccasins Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 stars(3)

TimberlandMen's Newmarket Chukka Leather Boots

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)

ECCOMen's Metropole Milan Suede Chukka Boots

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)

Johnston & MurphyBoys' Calder Leather Hook-and-Loop Chukka Boots (Toddler)

To Boot New YorkMen's Vista Chukka Boots

Internet Exclusive
Extended Sizes

Twisted XWomen's Sunflower Leather Driving Moc Toe Chukka Boots

Extended Sizes
Rated 3 out of 5 starsRated 3 out of 5 starsRated 3 out of 5 starsRated 3 out of 5 starsRated 3 out of 5 stars(2)

Twisted XWomen's Embroidered Moc Toe Driving Chukka Booties

Internet Exclusive
Extended Sizes

Twisted XMen's Driving Woven Leather Moccasin Chukka Boots

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)

FryeMen's Astor Leather Chukka Boots

Internet Exclusive
Rated 4.2308 out of 5 starsRated 4.2308 out of 5 starsRated 4.2308 out of 5 starsRated 4.2308 out of 5 starsRated 4.2308 out of 5 stars(13)

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)

Bed StuMen's Illiad Leather Chukka Boots

Twisted XWomen's Tooled Turquoise Stud Driving Moc Toe Chukka Boots

Extended Sizes
Rated 4 out of 5 starsRated 4 out of 5 starsRated 4 out of 5 starsRated 4 out of 5 starsRated 4 out of 5 stars(5)

Twisted XWomen's Embroidered Leather Driving Moc Toe Chukka Boots

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(7)

BornMen's Harrison Leather Chukka Boots

Internet Exclusive
Extended Sizes
Rated 4.697 out of 5 starsRated 4.697 out of 5 starsRated 4.697 out of 5 starsRated 4.697 out of 5 starsRated 4.697 out of 5 stars(33)

UGGMen's Chukka Lug Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

BirkenstockWomen's Uppsala Shearling Lined Suede Chukka Booties

Permanently Reduced
Orig.
Now
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(5)

Johnston & MurphyMen's XC+Parker Waterproof Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.7143 out of 5 starsRated 4.7143 out of 5 starsRated 4.7143 out of 5 starsRated 4.7143 out of 5 starsRated 4.7143 out of 5 stars(7)

Johnston & MurphyMen's Braxton Oiled Leather Chukka Boots

Permanently Reduced
Orig.
Now
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)

Dr. MartensWomen's Charlee Chukka Nubuck Suede Combat Booties

Permanently Reduced
Orig.
Now
Extended Sizes
Only size 8 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)

UGGMen's Lug Chukka Boots

Permanently Reduced
Orig.
Now
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)

Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Johnston & MurphyMen's Upton Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

Polo Ralph LaurenMen's Asher Suede Chukka Boots

Permanently Reduced
Orig.
Now

Johnston & MurphyMen's Calder 175th Anniversary Leather Chukka Boots

Permanently Reduced
Orig.
Now
Rated 4.3333 out of 5 starsRated 4.3333 out of 5 starsRated 4.3333 out of 5 starsRated 4.3333 out of 5 starsRated 4.3333 out of 5 stars(3)

Johnston & MurphyMen's Larkin Leather Plain Toe Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.1111 out of 5 starsRated 4.1111 out of 5 starsRated 4.1111 out of 5 starsRated 4.1111 out of 5 starsRated 4.1111 out of 5 stars(9)

Johnston & MurphyBoys' McGuffey Leather Alternative Closure Chukka Boots (Toddler)

Permanently Reduced
Orig.
Now
Rated 4.9231 out of 5 starsRated 4.9231 out of 5 starsRated 4.9231 out of 5 starsRated 4.9231 out of 5 starsRated 4.9231 out of 5 stars(13)

Flag LTD.Men's Ayden Moc Toe Waterproof Leather Lace Up Chukka Boots

Permanently Reduced
Orig.
Now
Dillard's Exclusive

Cole HaanMen's 2.ZERØGRAND Suede Chukka Boots

Permanently Reduced
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(1)

Johnston & MurphyBoys' McGuffey Leather Lace Up Chukka Boots (Youth)

Permanently Reduced
Orig.
Now
Rated 4.9375 out of 5 starsRated 4.9375 out of 5 starsRated 4.9375 out of 5 starsRated 4.9375 out of 5 starsRated 4.9375 out of 5 stars(16)

Johnston & MurphyBoys' McGuffey Leather Hook-and-Loop Chukka Boots (Infant)

Permanently Reduced
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(7)
Twisted X Men's Leather Lace-Up Chukka Driving MoccasinsMen's Leather Lace-Up Chukka Driving Moccasins

Twisted XMen's Leather Lace-Up Chukka Driving Moccasins

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 starsRated 4.6667 out of 5 stars(3)
  • 67 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. © 2026 Dillard's

***