Skip to main content

Enjoy Holiday Savings on New In-Season Markdowns up to 33% - 40% off select styles - SHOP NOW

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

The 2025 Dillard's Christmas Gift Guide is here - Volume 5 - 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
Shop Dillards.com - The Style of Christmas
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

New Arrivals
  • New Arrivals
Sale
  • Sale

Category

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

Brand

search
Brand
  • ALDO
  • ALIGN
  • Ariat
  • Bed Stu
  • Birkenstock
  • Blondo
  • Born
  • Clarks
  • COACH
  • Cole Haan
  • Danner
  • Dr. Scholl's
  • Dune London
  • Eastland
  • ECCO
  • Flag LTD.
  • Frye
  • Gentle Souls
  • Johnston & Murphy
  • Josef Seibel
  • Kurt Geiger London
  • L.L.Bean
  • Merrell
  • Minnetonka
  • Polo Ralph Lauren
  • Ryka
  • SAS
  • Skechers
  • Sofft
  • Sorel
  • Steve Madden
  • Stride Rite
  • Timberland
  • To Boot New York
  • Twisted X
  • UGG
  • Vintage Havana
color
  • Black
  • Grey
  • Ivory
  • Tan
  • Brown
  • Red
  • Pink
  • Green
  • Blue
  • Animal
styling feature
  • Bit Buckle
  • Fringe
  • Hardware
  • Ornament
  • Penny Keeper
  • Signature Logo
  • Studs
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
  • Snowboot
  • T-Strap
  • Venetian
  • Western
  • Winter
  • Work Boot
platform height
  • Flat
  • High
  • Low
  • Mid
  • Ultra-High
  • All
  • Women's Shoes
  • Kids' Shoes
  • Men's Shoes
clear allChukkaclear filter
  • 158 Items
  • First
  • Previous Page
  • 1
  • 2
Twisted X Men's Chukka Driving CellStretch MocsMen's Chukka Driving CellStretch Mocs

Twisted XMen's Chukka Driving CellStretch Mocs

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)
COACH Men's Lug Sole Leather BootsMen's Lug Sole Leather Boots

COACHMen's Lug Sole Leather 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)
Timberland Women's Stone Street Mid Lace Up Waterproof Chukka BootiesWomen's Stone Street Mid Lace Up Waterproof Chukka Booties

TimberlandWomen's Stone Street Mid Lace Up Waterproof Chukka Booties

Internet Exclusive
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)
Sorel Men's Slabtown 62' Stoic Suede Chukka BootsMen's Slabtown 62' Stoic Suede Chukka Boots

SorelMen's Slabtown 62' Stoic Suede Chukka 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)
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 5.0 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 & Murphy Boys' McGuffey Leather Hook-and-Loop Chukka Boots (Infant)Boys' McGuffey Leather Hook-and-Loop Chukka Boots (Infant)

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

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)
Ryka Women's Charisma Ankle BootiesWomen's Charisma Ankle Booties

RykaWomen's Charisma Ankle Booties

Internet Exclusive
Extended Sizes
Only size 11 available
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(5)
Sorel Men's Madson II Moc Toe Waterproof BootsMen's Madson II Moc Toe Waterproof Boots

SorelMen's Madson II Moc Toe Waterproof Boots

Internet Exclusive
Rated 4.6154 out of 5 starsRated 4.6154 out of 5 starsRated 4.6154 out of 5 starsRated 4.6154 out of 5 starsRated 4.6154 out of 5 stars(13)
Born Men's Nigel Suede Lace-Up BootsMen's Nigel Suede Lace-Up Boots

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)

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

Dillard's Exclusive

Twisted XMen's Work Composite Toe Slip On Driving Moccasins

Internet Exclusive
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)

ECCOMen's Metropole Milan Suede Chukka Boots

Cole HaanMen's Muir Waterproof Suede Moc Toe Boots

Internet Exclusive

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

Dr. Scholl'sOriginal Chic Platform Booties

Extended Sizes
Rated 4.4444 out of 5 starsRated 4.4444 out of 5 starsRated 4.4444 out of 5 starsRated 4.4444 out of 5 starsRated 4.4444 out of 5 stars(9)

Steve MaddenGirls 'T-Glazer Charm Boots (Infant)

Limited Availability

L.L.BeanMen's Eco Bay Nubuck Chukka Boots

COACHMen's Sculpt C Suede Chukka Oxfords

Internet Exclusive

To Boot New YorkMen's Vista Chukka Boots

Internet Exclusive
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)

Bed StuMen's Lincoln Lace Up Leather Boots

Twisted XMen's Driving Moccasin Chukka Boots

Internet Exclusive
Extended Sizes

DannerWomen's Inquire Chukka Waterproof Leather Hiking Boots

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

Extended Sizes

Twisted XMen's Chukka Driving Moccasins

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)

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)

ALDOMen's Farrell Leather Lace Up Boots

Internet Exclusive
Extended Sizes

Cole HaanMen's Muir Leather Moc Toe Boots

Internet Exclusive

Bed StuMen's Illiad Leather Chukka Boots

COACHSculpted C Suede Chukka Oxfords

Internet Exclusive
Extended Sizes
Only size 10 available

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)

Twisted XWomen's Sunflower Leather Driving Moc Toe Chukka Boots

Internet Exclusive
Extended Sizes
Rated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 starsRated 3.0 out of 5 stars(2)

MinnetonkaKids' Suede Fringe Detail Tramper Boots (Toddler)

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)

Dune LondonMen's Smoky Leather Casual Ankle Boots

Internet Exclusive

MinnetonkaKids' Suede Fringe Softsole Boots (Toddler)

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)

MinnetonkaKids' Suede Fringe Detail Tramper Boots (Infant)

Internet Exclusive

MinnetonkaWomen's Torrey Suede Striped Fabric Faux Fur Lined Booties

Internet Exclusive
Extended Sizes

Flag LTD.Boys' Freddie Camouflage Lace Up Boots (Toddler)

Dillard's Exclusive

Twisted XMen's Chukka Driving Mocs

Internet Exclusive
Extended Sizes

MinnetonkaKids' Suede Fringe Softsole Boots (Infant)

Internet Exclusive

MinnetonkaKids' Braid Bootie Crib Shoes (Infant)

Internet Exclusive

MinnetonkaKids' Suede Fringe Detail Tramper Boots (Youth)

Internet Exclusive

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

Internet Exclusive
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)

MinnetonkaGirls' Front Strap Fringe Detail 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)

MinnetonkaKids' Suede Fringe Softsole Boots (Youth)

Internet Exclusive
Rated 1.0 out of 5 starsRated 1.0 out of 5 starsRated 1.0 out of 5 starsRated 1.0 out of 5 starsRated 1.0 out of 5 stars(1)

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 ECO Moc-Toe Lace Up Boot

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)

EastlandMen's Jack Chukka Boots

Internet Exclusive
Only size 10 available

UGGEsmee Lace Up Suede Platform Booties

Permanently Reduced
Orig.
Now
Extended Sizes

Kurt Geiger LondonMansion Cozy Studded Suede Bit Buckle Platform Boots

Permanently Reduced
Orig.
Now
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)

UGGEsmee Lace Up Leather Platform Booties

Permanently Reduced
Orig.
Now
Extended Sizes

BlondoMonday Waterproof Suede Faux Fur Booties

Limited Time Offer
Orig.
Now
Extended Sizes

UGGMen's Chukka Lug Suede Boots

Permanently Reduced
Orig.
Now
Extended Sizes

UGGMen's Lug 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)

Steve MaddenMen's Tabriz Lace Up Leather Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes

UGGMen's Neumel Crafted Regenerate Boots

Permanently Reduced
Orig.
Now

BlondoKayloni Waterproof Leather Lug Sole Booties

Limited Time Offer
Orig.
Now
Extended Sizes

Cole HaanMen's 2.ZERØGRAND Suede Chukka Boots

Permanently Reduced
Orig.
Now
Internet Exclusive

SofftLonnie Leather Zip Booties

Limited Time Offer
Orig.
Now
Internet Exclusive
Extended Sizes

Johnston & MurphyMen's Larkin Leather Plain Toe Chukka Boots

Permanently Reduced
Orig.
Now
Extended Sizes
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)
  • 158 Items
  • First
  • Previous Page
  • 1
  • 2

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

***