Skip to main content

Free Gift With Any $39.50 Estée Lauder Purchase* - 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

Back In Stock
Sale and Clearance
Shop By Brand
Limited Availability
Credit Card
Find a Store

SearchWhen typing in this field, a list of search results will appear and be automatically updated as you type.

Login
My Dillard's Account
Just For You
Order History
Returns
My Wish List
Find a Store

(0) items in cart

Women
Juniors
Men
Kids
Shoes
Handbags
Accessories
Lingerie
Home
Beauty
Dillard's Exclusive
Just For You

Leather Chukkas

Related Pages

Full-Grain Leather Chukkas Leather Moccasins Timberland Chukka Boots Moccasin Toe Chukka Boots Men's Winter Chukka Boots Nubuck Chelsea Boots Leather Buckle Shoes Leather Mules Suede Chelsea Boots Black Suede Chelsea Boots Leather Fisherman Shoes Deerskin Loafers Leather Square Toe Shoes Leather Brogue Shoes Dr. Scholl's Leather Sneakers Leather Moc Toe Loafers Leather Dansko Clogs Vintage Leather Shoes Leather Cap-Toe Dress Shoes Red Leather Shoes Ariat Chukka Boots Leather Derby Shoes Italian Chelsea Boots Pull-On Chelsea Boots Chunky Lace-Up Shoes Everyday Leather Shoes Men's Leather Slip On Loafers Brush Leather Shoes Frye Chelsea Boots Leather Platform Mules

SaleSale

Brand

When typing in this field, a list of search results will appear and be automatically updated as you type.

Brand

AriatAriat
Bed StuBed Stu
BornBorn
Cole HaanCole Haan
DannerDanner
Flag Ltd.Flag Ltd.
FryeFrye
Josef SeibelJosef Seibel
SorelSorel
TimberlandTimberland
To Boot New YorkTo Boot New York
Twisted XTwisted X

color

BlackBlack
BrownBrown
GreyGrey
MoroMoro
MultiMulti
NeutralNeutral
T-MoroT-Moro
TeakTeak

Sort By

41 Items

Men's Paul Leather Chukka Boots

Men's Paul Leather Chukka Boots

Frye Men's Paul Leather Chukka Boots

Men's Upton Leather Chukka Boots

Men's Upton Leather Chukka Boots

Johnston & Murphy Men's Upton Leather Chukka Boots

Permanently Reduced

Men's Harrison Leather Chukka Boots

Men's Harrison Leather Chukka Boots

Born Men's Harrison Leather Chukka Boots

Internet Exclusive

Men's Driving Leather Moc Toe Chukka Boots

Men's Driving Leather Moc Toe Chukka Boots

Twisted X Men's Driving Leather Moc Toe Chukka Boots

Men's Lookout Leather Chukka Boots

Men's Lookout Leather Chukka Boots

Ariat Men's Lookout Leather Chukka Boots

Only size 11 available

Men's Astor Leather Chukka Boots

Men's Astor Leather Chukka Boots

Frye Men's Astor Leather Chukka Boots

Save on Select Items

Now $152.76 - $228.00

Men's Calder Leather Chukka Lace Up Boots

Men's Calder Leather Chukka Lace Up Boots

Johnston & Murphy Men's Calder Leather Chukka Lace Up Boots

Men's Driving Woven Leather Moccasin Chukka Boots

Men's Driving Woven Leather Moccasin Chukka Boots

Twisted X Men's Driving Woven Leather Moccasin Chukka Boots

Men's Illiad Leather Chukka Boots

Men's Illiad Leather Chukka Boots

Bed Stu Men's Illiad Leather Chukka Boots

Men's Morse Leather Chukka Boots

Men's Morse Leather Chukka Boots

Cole Haan Men's Morse Leather Chukka Boots

Internet Exclusive

Men's Braxton Oiled Leather Chukka Boots

Men's Braxton Oiled Leather Chukka Boots

Johnston & Murphy Men's Braxton Oiled Leather Chukka Boots

Permanently Reduced

Women's Embroidered Leather Driving Moc Toe Chukka Boots

Women's Embroidered Leather Driving Moc Toe Chukka Boots

Twisted X Women's Embroidered Leather Driving Moc Toe Chukka Boots

Men's Driving CellStretch Leather Moc Toe Chukka Boots

Men's Driving CellStretch Leather Moc Toe Chukka Boots

Twisted X Men's Driving CellStretch Leather Moc Toe Chukka Boots

Men's Slip-On Chukka Leather Driving Moccasin Boots

Men's Slip-On Chukka Leather Driving Moccasin Boots

Twisted X Men's Slip-On Chukka Leather Driving Moccasin Boots

Internet Exclusive

Men's Split Rock Leather Moc Toe Chukka Boots

Men's Split Rock Leather Moc Toe Chukka Boots

Ariat Men's Split Rock Leather Moc Toe Chukka Boots

Women's Original Leather Driving Moc Toe Chukka Boots

Women's Original Leather Driving Moc Toe Chukka Boots

Twisted X Women's Original Leather Driving Moc Toe Chukka Boots

Women's Printed Leather Driving Moc Toe Chukka Boots

Women's Printed Leather Driving Moc Toe Chukka Boots

Twisted X Women's Printed Leather Driving Moc Toe Chukka Boots

Men's Chamberlin Water Resistant Nubuck Chukka Boots

Men's Chamberlin Water Resistant Nubuck Chukka Boots

Cole Haan Men's Chamberlin Water Resistant Nubuck Chukka Boots

Men's XC+Parker Waterproof Leather Chukka Boots

Men's XC+Parker Waterproof Leather Chukka Boots

Johnston & Murphy Men's XC+Parker Waterproof Leather Chukka Boots

Permanently Reduced

Men's Chukka Driving Moccasins

Men's Chukka Driving Moccasins

Twisted X Men's Chukka Driving Moccasins

Internet Exclusive

Men's Chukka Hiker Waterproof Boots

Men's Chukka Hiker Waterproof Boots

Twisted X Men's Chukka Hiker Waterproof Boots

Internet Exclusive

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

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

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

Permanently Reduced

Dillard´s Exclusive

Men's Earl 04 Leather Lace Up Chukka Boots

Men's Earl 04 Leather Lace Up Chukka Boots

Josef Seibel Men's Earl 04 Leather Lace Up Chukka Boots

Men's Paul Chukka Lite Boots

Men's Paul Chukka Lite Boots

Frye Men's Paul Chukka Lite Boots

$ 189.00 - $ 198.00

Internet Exclusive

Men's Vista Chukka Boots

Men's Vista Chukka Boots

To Boot New York Men's Vista Chukka Boots

Permanently Reduced

Internet Exclusive

Only size 8.5, 9 available

Men's Madson II Waterproof Leather Chukka Boots

Men's Madson II Waterproof Leather Chukka Boots

Sorel Men's Madson II Waterproof Leather Chukka Boots

Internet Exclusive

Only size 7, 7.5 available

Women's Sunflower Leather Driving Moc Toe Chukka Boots

Women's Sunflower Leather Driving Moc Toe Chukka Boots

Twisted X Women's Sunflower Leather Driving Moc Toe Chukka Boots

Internet Exclusive

Men's Calder 175th Anniversary Leather Chukka Boots

Men's Calder 175th Anniversary Leather Chukka Boots

Johnston & Murphy Men's Calder 175th Anniversary Leather Chukka Boots

Permanently Reduced

Men's Erroll 52 Chukka Boots

Men's Erroll 52 Chukka Boots

Josef Seibel Men's Erroll 52 Chukka Boots

Men's Waterproof Driving Moccasins Chukka Boots

Men's Waterproof Driving Moccasins Chukka Boots

Twisted X Men's Waterproof Driving Moccasins Chukka Boots

Boys' McGuffey Leather Lace Up Chukka Boots (Youth)

Boys' McGuffey Leather Lace Up Chukka Boots (Youth)

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

Permanently Reduced

Internet Exclusive

Women's Tooled Moc Toe Driving Chukka Booties

Women's Tooled Moc Toe Driving Chukka Booties

Twisted X Women's Tooled Moc Toe Driving Chukka Booties

Men's Work Steel Toe Leather Chukka Driving Moccasins

Men's Work Steel Toe Leather Chukka Driving Moccasins

Twisted X Men's Work Steel Toe Leather Chukka Driving Moccasins

Women's Embroidered Moc Toe Driving Chukka Booties

Women's Embroidered Moc Toe Driving Chukka Booties

Twisted X Women's Embroidered Moc Toe Driving Chukka Booties

Internet Exclusive

Women's Stone Street Mid Lace Up Waterproof Chukka Booties

Women's Stone Street Mid Lace Up Waterproof Chukka Booties

Timberland Women's Stone Street Mid Lace Up Waterproof Chukka Booties

Internet Exclusive

Analia Distressed Suede Ankle Chukka Booties

Analia Distressed Suede Ankle Chukka Booties

Born Analia Distressed Suede Ankle Chukka Booties

Women's Inquire Chukka Waterproof Leather Hiking Boots

Women's Inquire Chukka Waterproof Leather Hiking Boots

Danner Women's Inquire Chukka Waterproof Leather Hiking Boots

Women's Tooled Turquoise Stud Driving Moc Toe Chukka Boots

Women's Tooled Turquoise Stud Driving Moc Toe Chukka Boots

Twisted X Women's Tooled Turquoise Stud Driving Moc Toe Chukka Boots

Internet Exclusive

Boys' Calder Leather Lace Up Chukka Boots (Youth)

Boys' Calder Leather Lace Up Chukka Boots (Youth)

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

Boys' Calder Leather Hook-and-Loop Chukka Boots (Infant)

Boys' Calder Leather Hook-and-Loop Chukka Boots (Infant)

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

Boys' Calder Leather Hook-and-Loop Chukka Boots (Toddler)

Boys' Calder Leather Hook-and-Loop Chukka Boots (Toddler)

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

41 Items

About Leather Chukkas

Discover the timeless appeal of leather chukkas, a versatile footwear choice that combines style and comfort. These ankle-high boots are crafted from premium leather, providing durability and a sophisticated look suitable for various occasions. With their classic silhouette and modern designs, leather chukkas can effortlessly elevate both casual and semi-formal outfits.

Designed for all-day wear, leather chukkas feature cushioned insoles and sturdy outsoles for enhanced comfort and support. Available in a range of colors and finishes, these boots offer a perfect blend of functionality and fashion, making them a staple in any wardrobe.

What are leather chukkas?

Leather chukkas are ankle-length boots typically made from high-quality leather. They are characterized by their simple design, often featuring two or three eyelets for laces, making them easy to wear and style.

Are leather chukkas suitable for formal occasions?

Yes, leather chukkas can be suitable for formal occasions, especially when paired with tailored trousers or chinos. Their sleek design and premium materials add a touch of sophistication to smart-casual and business-casual outfits.

How do I style leather chukkas?

Leather chukkas can be styled in various ways, making them versatile for different looks. They pair well with jeans, chinos, and even dress pants, and can be complemented with casual shirts, blazers, or sweaters for a polished appearance.

What makes leather chukkas comfortable?

Leather chukkas are designed with comfort in mind, featuring cushioned insoles and flexible outsoles that provide support during extended wear. The natural breathability of leather also helps keep feet comfortable throughout the day.

Can leather chukkas be worn in different seasons?

Yes, leather chukkas are versatile enough to be worn in various seasons. They can be paired with lighter fabrics in warmer months and layered with socks or heavier clothing during colder seasons, making them a year-round footwear option.

How do leather chukkas differ from other boot styles?

Leather chukkas differ from other boot styles primarily in their height and design. They are shorter than traditional boots, typically reaching just above the ankle, and feature a more casual aesthetic compared to dress boots or work boots.

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!

Email sign-up

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.

Text sign-up

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.

Opens Dillard's Instagram in a new window
Opens Dillard's Facebook in a new window
Opens Dillard's Pinterest in a new window
Opens Dillard's Twitter/X in a new window
Opens Dillard's YouTube in a new window
Opens Dillard's TikTok in a new window
Opens 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

***