Skip to main content

End of Season Clearance - Enjoy savings up to 65% off select styles - SHOP NOW

Free 6-Piece Gift with Any Estee Lauder Purchase of $75 or More!* - SHOP NOW

iPhone Updates & 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

leather brown : Shoes : Chukka

Sale
  • Sale

Category

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

Brand

search
Brand
  • ALDO
  • ALIGN
  • Ariat
  • Bed Stu
  • Born
  • Cole Haan
  • Danner
  • Dune London
  • Flag LTD.
  • Frye
  • Johnston & Murphy
  • Josef Seibel
  • L.L.Bean
  • Minnetonka
  • Polo Ralph Lauren
  • Skechers
  • Sorel
  • Steve Madden
  • Timberland
  • To Boot New York
  • Twisted X
  • UGG
styling feature
  • Fringe
  • Studs
platform height
  • Flat
  • High
  • Low
shoe silhouette
  • Ankle/Quarter Strap
  • Ballerina
  • Banded
  • Boat Shoe
  • Chelsea
  • Chukka
  • Classic
  • Clog
  • Driver
  • Engineer
  • Espadrille
  • Fisherman
  • Flat
  • Flip Flop
  • Gladiator
  • Hiker
  • Huarache
  • Loafer
  • Mary Jane
  • Moccasin
  • Monk Strap
  • Moto/Combat
  • Mule
  • Open Shank (d'Orsay)
  • Oxford
  • Pump
  • Rain
  • Riding
  • Saddle/Buc
  • Shootie
  • Slide
  • Slingback
  • Slip-On
  • Sneaker
  • T-Strap
  • Venetian
  • Western
  • Winter
  • Work Boot
  • All
  • Women's Shoes
  • Men's Shoes
  • Kids' Shoes
clear allChukkaclear filter
  • 69 Items
UGG Men's Idyllwild Leather Lace BootsMen's Idyllwild Leather Lace Boots

UGGMen's Idyllwild Leather Lace Boots

Extended Sizes
Polo Ralph Lauren Men's Ranger Tumbled Leather Buckle Lug Sole BootsMen's Ranger Tumbled Leather Buckle Lug Sole Boots

Polo Ralph LaurenMen's Ranger Tumbled Leather Buckle Lug Sole Boots

Extended Sizes
Rated 4.6522 out of 5 starsRated 4.6522 out of 5 starsRated 4.6522 out of 5 starsRated 4.6522 out of 5 starsRated 4.6522 out of 5 stars(46)
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)
Timberland Women's Stone Street Leather Kiltie Lace Up BootsWomen's Stone Street Leather Kiltie Lace Up Boots

TimberlandWomen's Stone Street Leather Kiltie Lace Up Boots

Extended Sizes
Rated 4.8254 out of 5 starsRated 4.8254 out of 5 starsRated 4.8254 out of 5 starsRated 4.8254 out of 5 starsRated 4.8254 out of 5 stars(63)
Twisted X Men's Waterproof Driving Moccasins Chukka BootsMen's Waterproof Driving Moccasins Chukka Boots

Twisted XMen's Waterproof Driving Moccasins Chukka Boots

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)
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)

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(2)
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 2.0 out of 5 starsRated 2.0 out of 5 starsRated 2.0 out of 5 starsRated 2.0 out of 5 starsRated 2.0 out of 5 stars(1)
Ariat Men's Spitfire BootsMen's Spitfire Boots

AriatMen's Spitfire Boots

Extended Sizes
Rated 4.7192 out of 5 starsRated 4.7192 out of 5 starsRated 4.7192 out of 5 starsRated 4.7192 out of 5 starsRated 4.7192 out of 5 stars(317)
Men's Idyllwild Leather Lace Boots

PLACEHOLDERMen's Idyllwild Leather Lace 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)

FryeMen's Astor Leather Chukka Boots

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)

PLACEHOLDERMen's Idyllwild Leather Lace Boots

Extended Sizes

Bed StuMen's Illiad Leather Chukka Boots

Johnston & MurphyMen's XC+ Durham Waterproof Leather Cap Toe Boots

Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(5)

PLACEHOLDERMen's Idyllwild Leather Lace Boots

Extended Sizes

BornCalyn Distressed Leather Lace Ankle Booties

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Twisted XMen's Work Composite Toe Slip On Driving Moccasins

Extended Sizes
Rated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 stars(1)

PLACEHOLDERMen's Idyllwild Leather Lace Boots

Extended Sizes

L.L.BeanMen's Stonington Leather Moc Toe Boots

Extended Sizes
Rated 4.637 out of 5 starsRated 4.637 out of 5 starsRated 4.637 out of 5 starsRated 4.637 out of 5 starsRated 4.637 out of 5 stars(449)

Twisted XMen's Moc Toe Leather Lace Up Boots

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(3)

Twisted XMen's Driving Leather Moc Toe Chukka Boots

Extended Sizes

Cole HaanMen's Morse Leather Chukka Boots

BornMen's Nigel Leather Lace Up Boots

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(3)

TimberlandMen's Redwood Edge Leather Lace Up Boots

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(2)

Twisted XWomen's Embroidered Leather Driving Moc Toe Chukka Boots

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(7)

Josef SeibelMen's Earl 04 Leather Lace Up Chukka Boots

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(6)

AriatMen's Spitfire Waterproof Leather Boots

Extended Sizes
Rated 4.4667 out of 5 starsRated 4.4667 out of 5 starsRated 4.4667 out of 5 starsRated 4.4667 out of 5 starsRated 4.4667 out of 5 stars(45)

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

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)

Twisted XMen's 4" Woven Leather Boots

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(2)

Twisted XMen's Cellstretch® Wedge Sole Boots

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

DannerWomen's Mountain Light Cascade Iconic Hiking Boots

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Twisted XWomen's Sunflower Leather Driving Moc Toe Chukka Boots

Extended Sizes

SorelMen's Cyprus Waterproof Leather Boots

Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

AriatMen's Split Rock Leather Moc Toe Chukka Boots

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(4)

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)

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

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)

AriatMen's Lookout Leather Chukka Boots

Only size 11 available
Rated 4.1159 out of 5 starsRated 4.1159 out of 5 starsRated 4.1159 out of 5 starsRated 4.1159 out of 5 starsRated 4.1159 out of 5 stars(69)

BornMen's Nigel Suede Lace-Up Boots

Internet Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

Bed StuMen's Lincoln Lace Up Leather Boots

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

DannerWomen's Inquire Chukka Waterproof Leather Hiking Boots

Extended Sizes

ALDOMen's Farrell Leather Lace Up Boots

Extended Sizes

Twisted XWomen's Printed Leather Driving Moc Toe Chukka Boots

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(2)

Twisted XMen's Chukka Driving CellStretch Mocs

Internet Exclusive
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

Twisted XWomen's Embroidered Moc Toe Driving Chukka Booties

Internet Exclusive
Extended Sizes

Twisted XMen's Work Steel Toe Leather Chukka Driving Moccasins

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

Twisted XMen's Chukka Driving Mocs

Extended Sizes

MinnetonkaKids' Fringe Bootie Crib Shoes (Infant)

Internet Exclusive
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

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

Extended Sizes
Rated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 starsRated 4.0 out of 5 stars(5)

Twisted XMen's Driving Leather Moccasin Chukka Boots

Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(8)

Twisted XWomen's Tooled Moc Toe Driving Chukka Booties

Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(8)

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)

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

Permanently Reduced
Orig.
Now
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(5)

Johnston & MurphyMen's Upton Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

BornMen's Brock Distressed Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(9)

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

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.7778 out of 5 starsRated 4.7778 out of 5 starsRated 4.7778 out of 5 starsRated 4.7778 out of 5 starsRated 4.7778 out of 5 stars(9)

SkechersMen's Slip-ins Relaxed Fit: Respected 2.0 - Hagler Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Only size 8, 10 available

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)

ALIGNMen's Rivers Weatherproof Tumbled Leather Boots

Permanently Reduced
Orig.
Now

To Boot New YorkMen's Vista Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

TimberlandMen's Redwood Falls Waterproof Leather Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive
Extended Sizes
Only size 11.5 available
Rated 4.3768 out of 5 starsRated 4.3768 out of 5 starsRated 4.3768 out of 5 starsRated 4.3768 out of 5 starsRated 4.3768 out of 5 stars(69)

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

Permanently Reduced
Orig.
Now
Rated 3.9189 out of 5 starsRated 3.9189 out of 5 starsRated 3.9189 out of 5 starsRated 3.9189 out of 5 starsRated 3.9189 out of 5 stars(37)

Johnston & MurphyMen's Braxton Oiled Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 starsRated 5.0 out of 5 stars(1)

Johnston & MurphyMen's Barret Leather Plain Toe Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.1429 out of 5 starsRated 4.1429 out of 5 starsRated 4.1429 out of 5 starsRated 4.1429 out of 5 starsRated 4.1429 out of 5 stars(7)

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

Permanently Reduced
Orig.
Now
Dillard's Exclusive

SorelMen's Slabtown 62 Moc Waterproof Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.4211 out of 5 starsRated 4.4211 out of 5 starsRated 4.4211 out of 5 starsRated 4.4211 out of 5 starsRated 4.4211 out of 5 stars(38)

Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 2.0 out of 5 starsRated 2.0 out of 5 starsRated 2.0 out of 5 starsRated 2.0 out of 5 starsRated 2.0 out of 5 stars(1)
Johnston & Murphy Men's Larkin Leather Plain Toe Chukka BootsMen's Larkin Leather Plain Toe Chukka Boots

Johnston & MurphyMen's Larkin Leather Plain Toe Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes
Rated 4.2 out of 5 starsRated 4.2 out of 5 starsRated 4.2 out of 5 starsRated 4.2 out of 5 starsRated 4.2 out of 5 stars(10)
  • 69 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

***