Skip to main content

President's Day 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

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

Comfortable Ankle Boots

Related Pages

Comfortable Heeled Boots Comfortable Combat Boots Comfortable Chunky Boots Buttery Soft Leather Ankle Boots Comfortable Hiking Boots Platform Ankle Boots Heeled Ankle Boots Women's Ankle Slouch Boots Children's Ankle Boots Chocolate Ankle Boots Strappy Ankle Boots Western-Style Ankle Boots Work Ankle Boots Lightweight Ankle Boots Comfortable Moto Boots Comfortable Steel-Toe Boots Fall Ankle Boots Chelsea Ankle Boots Genuine Leather Ankle Boots Women's Vintage Ankle Boots Ankle Boots With Arch Support Cut-Out Ankle Boots Insulated Ankle Boots Versatile Boots Fold-Over Ankle Boots Suede Fringe Ankle Boots Brown Ankle Boots Ankle Harness Boots Ankle-Height Hiking Boots Rubber Sole Ankle Boots

SaleSale

Brand

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

Brand

color

BlackBlack
BlueBlue
BrownBrown
GreenGreen
GreyGrey
IvoryIvory
OrangeOrange
PinkPink
RedRed
TanTan
WhiteWhite
YellowYellow

Sort By

134 Items
1
2
Next Page
Last

Kace Leather Ankle Booties

Kace Leather Ankle Booties

Born Kace Leather Ankle Booties

Cici Leather Chelsea Ankle Booties

Cici Leather Chelsea Ankle Booties

Born Cici Leather Chelsea Ankle Booties

Lorrys Slouchy Suede Ankle Boots

Lorrys Slouchy Suede Ankle Boots

Vince Camuto Lorrys Slouchy Suede Ankle Boots

Permanently Reduced

Ailein Suede Ankle Booties

Lucky Brand Ailein Suede Ankle Booties

Permanently Reduced

Petty Leather Ankle Booties

Petty Leather Ankle Booties

Sam Edelman Petty Leather Ankle Booties

Ailein Nubuck Ankle Booties

Lucky Brand Ailein Nubuck Ankle Booties

Permanently Reduced

Oaklee Leather Dual Zip Ankle Booties

Oaklee Leather Dual Zip Ankle Booties

Alegria Oaklee Leather Dual Zip Ankle Booties

Internet Exclusive

Rowan Leather Tassel Ankle Booties

Rowan Leather Tassel Ankle Booties

Born Rowan Leather Tassel Ankle Booties

Save on Select Items

Now $63.00 - $180.00

Analia Distressed Suede Ankle Chukka Booties

Analia Distressed Suede Ankle Chukka Booties

Born Analia Distressed Suede Ankle Chukka Booties

Jade Leather Wedge Ankle Booties

Jade Leather Wedge Ankle Booties

SAS Jade Leather Wedge Ankle Booties

Calyn Distressed Leather Lace Ankle Booties

Calyn Distressed Leather Lace Ankle Booties

Born Calyn Distressed Leather Lace Ankle Booties

Bethany Side Zip Ankle Booties

Bethany Side Zip Ankle Booties

SAS Bethany Side Zip Ankle Booties

Cici Suede Chelsea Ankle Booties

Cici Suede Chelsea Ankle Booties

Born Cici Suede Chelsea Ankle Booties

Lira Leather Ankle Booties

Lira Leather Ankle Booties

SoftWalk Lira Leather Ankle Booties

Internet Exclusive

Aldaya Leather Zip Ankle Booties

Aldaya Leather Zip Ankle Booties

Pikolinos Aldaya Leather Zip Ankle Booties

Jill Suede Booties

Jill Suede Booties

Vionic Jill Suede Booties

Permanently Reduced

Internet Exclusive

Only size 11 available

Kace Distressed Leather Ankle Booties

Kace Distressed Leather Ankle Booties

Born Kace Distressed Leather Ankle Booties

Greer Suede Zip Up Ankle Booties

Greer Suede Zip Up Ankle Booties

Vince Camuto Greer Suede Zip Up Ankle Booties

Permanently Reduced

Internet Exclusive

Cacti Suede Ankle Booties

Cacti Suede Ankle Booties

Gentle Souls Cacti Suede Ankle Booties

Permanently Reduced

Emma Suede Wedge Ankle Booties

Emma Suede Wedge Ankle Booties

Sofft Emma Suede Wedge Ankle Booties

Daney Suede Block Heel Ankle Booties

Daney Suede Block Heel Ankle Booties

Steve Madden Daney Suede Block Heel Ankle Booties

Permanently Reduced

Kalie Leather Ankle Booties

Kalie Leather Ankle Booties

Born Kalie Leather Ankle Booties

Permanently Reduced

Now $54.25 - $103.85

Cleo Suede Ankle Booties

Cleo Suede Ankle Booties

Matisse Cleo Suede Ankle Booties

Permanently Reduced

Internet Exclusive

Only size 6 available

Thia Distressed Leather Dual Zip Ankle Booties

Thia Distressed Leather Dual Zip Ankle Booties

Born Thia Distressed Leather Dual Zip Ankle Booties

Permanently Reduced

Only size 6.5 available

Bitsy Distressed Leather Square Toe Ankle Booties

Bitsy Distressed Leather Square Toe Ankle Booties

Bed Stu Bitsy Distressed Leather Square Toe Ankle Booties

Northmost Suede Ankle Booties

Northmost Suede Ankle Booties

Minnetonka Northmost Suede Ankle Booties

Internet Exclusive

Bridgett Waterproof Suede Ankle Booties

Bridgett Waterproof Suede Ankle Booties

Sofft Bridgett Waterproof Suede Ankle Booties

Permanently Reduced

Rylie Suede Ankle Booties

Rylie Suede Ankle Booties

TOMS Rylie Suede Ankle Booties

Permanently Reduced

Only size 7, 8 available

Women's Heeled Chelsea Booties

Women's Heeled Chelsea Booties

Blundstone Women's Heeled Chelsea Booties

Tourmaline Leather Dual Zip Ankle Booties

Tourmaline Leather Dual Zip Ankle Booties

ara Tourmaline Leather Dual Zip Ankle Booties

Permanently Reduced

Internet Exclusive

Only size 8 available

Kich Nubuck Lace Up Ankle Wedge Booties

Kich Nubuck Lace Up Ankle Wedge Booties

SAS Kich Nubuck Lace Up Ankle Wedge Booties

Isabella Leather Western Booties

Isabella Leather Western Booties

Justin Boots Isabella Leather Western Booties

Internet Exclusive

Women's Medina Leather Ankle Booties

Women's Medina Leather Ankle Booties

Pikolinos Women's Medina Leather Ankle Booties

Save on Select Items

Now $115.00 - $230.00

Kerri Leather Ankle Block Heel Booties

Kerri Leather Ankle Block Heel Booties

Born Kerri Leather Ankle Block Heel Booties

Easy Nubuck Chelsea Booties

Easy Nubuck Chelsea Booties

Bueno Easy Nubuck Chelsea Booties

Permanently Reduced

Internet Exclusive

Only size 40(9.5, 10) available

Emma Leather Wedge Ankle Booties

Emma Leather Wedge Ankle Booties

Sofft Emma Leather Wedge Ankle Booties

Kensington Suede Hiker Booties

Kensington Suede Hiker Booties

Kurt Geiger London Kensington Suede Hiker Booties

Permanently Reduced

Kalina Leather Ankle Booties

Kalina Leather Ankle Booties

Naturalizer Kalina Leather Ankle Booties

Permanently Reduced

Rowan Distressed Suede Tassel Detail Ankle Booties

Rowan Distressed Suede Tassel Detail Ankle Booties

Born Rowan Distressed Suede Tassel Detail Ankle Booties

Permanently Reduced

Redding Leather Buckle Ankle Booties

Redding Leather Buckle Ankle Booties

Vionic Redding Leather Buckle Ankle Booties

San Sebastian Leather Strappy Ankle Boots

San Sebastian Leather Strappy Ankle Boots

Pikolinos San Sebastian Leather Strappy Ankle Boots

Rochester Leather Ankle Buckle Booties

Rochester Leather Ankle Buckle Booties

SoftWalk Rochester Leather Ankle Buckle Booties

Internet Exclusive

Loralie Cashmere Suede Whipstitch Kitten Heel Ankle Boots

Loralie Cashmere Suede Whipstitch Kitten Heel Ankle Boots

Ron White Loralie Cashmere Suede Whipstitch Kitten Heel Ankle Boots

Permanently Reduced

Women's Jackpot Retro Hiker Inspired Ankle Booties

Women's Jackpot Retro Hiker Inspired Ankle Booties

Ryka Women's Jackpot Retro Hiker Inspired Ankle Booties

Permanently Reduced

Internet Exclusive

Only size 6 available

Fangio Lace Up Sport Sneaker Ankle Booties

Fangio Lace Up Sport Sneaker Ankle Booties

Steve Madden Fangio Lace Up Sport Sneaker Ankle Booties

Permanently Reduced

Vynn Leather Dress Ankle Booties

Vynn Leather Dress Ankle Booties

Vionic Vynn Leather Dress Ankle Booties

Permanently Reduced

Internet Exclusive

Only size 11 available

Vynn Suede Dress Ankle Booties

Vynn Suede Dress Ankle Booties

Vionic Vynn Suede Dress Ankle Booties

Permanently Reduced

Women's Vibrant Washable Chukka Platform Ankle Booties

Women's Vibrant Washable Chukka Platform Ankle Booties

Ryka Women's Vibrant Washable Chukka Platform Ankle Booties

Maude Suede Booties

Maude Suede Booties

TOMS Maude Suede Booties

Catina Leather Buckled Hardware Strap Ankle Booties

Catina Leather Buckled Hardware Strap Ankle Booties

Vionic Catina Leather Buckled Hardware Strap Ankle Booties

Permanently Reduced

Catina Suede Buckled Hardware Strap Ankle Booties

Catina Suede Buckled Hardware Strap Ankle Booties

Vionic Catina Suede Buckled Hardware Strap Ankle Booties

Permanently Reduced

Bia Leather Booties

Bia Leather Booties

Bed Stu Bia Leather Booties

Cora Leather Grommet Studded Ankle Booties

Cora Leather Grommet Studded Ankle Booties

Bueno Cora Leather Grommet Studded Ankle Booties

Internet Exclusive

Faithe Leather Buckle Hardware Block Heel Ankle Booties

Faithe Leather Buckle Hardware Block Heel Ankle Booties

Dansko Faithe Leather Buckle Hardware Block Heel Ankle Booties

Sculpted LX 35 O-Ring Leather Ankle Booties

Sculpted LX 35 O-Ring Leather Ankle Booties

ECCO Sculpted LX 35 O-Ring Leather Ankle Booties

Permanently Reduced

Harpher Leather Booties

Harpher Leather Booties

Lauren Ralph Lauren Harpher Leather Booties

Permanently Reduced

Internet Exclusive

Harpher Suede Booties

Harpher Suede Booties

Lauren Ralph Lauren Harpher Suede Booties

Permanently Reduced

Men's Smoky Leather Casual Ankle Boots

Men's Smoky Leather Casual Ankle Boots

Dune London Men's Smoky Leather Casual Ankle Boots

Internet Exclusive

Alivia Leather Booties

Lucky Brand Alivia Leather Booties

Permanently Reduced

Cherish Floral Embossed Leather Booties

Cherish Floral Embossed Leather Booties

L'ARTISTE Cherish Floral Embossed Leather Booties

Permanently Reduced

Rochester Nubuck Suede Ankle Buckle Booties

Rochester Nubuck Suede Ankle Buckle Booties

SoftWalk Rochester Nubuck Suede Ankle Buckle Booties

Internet Exclusive

Nash Suede Wedge Booties

Nash Suede Wedge Booties

Gentle Souls Nash Suede Wedge Booties

Permanently Reduced

Only size 8, 8.5 available

Elodie Woven Leather Booties

Elodie Woven Leather Booties

Gentle Souls Elodie Woven Leather Booties

Permanently Reduced

Internet Exclusive

Only size 7 available

Harp Square Toe Ankle Booties

Harp Square Toe Ankle Booties

Steve Madden Harp Square Toe Ankle Booties

Permanently Reduced

Best Elastic Leather Chelsea Booties

Best Elastic Leather Chelsea Booties

Gentle Souls Best Elastic Leather Chelsea Booties

Permanently Reduced

Internet Exclusive

Only size 11 available

Mini Chic Suede Faux Fur Lined Sneaker Ankle Booties

Mini Chic Suede Faux Fur Lined Sneaker Ankle Booties

Taos Footwear Mini Chic Suede Faux Fur Lined Sneaker Ankle Booties

Permanently Reduced

Internet Exclusive

Only size 9 available

Elsbury Leather Chelsea O-Ring Harness Hardware Ankle Booties

Elsbury Leather Chelsea O-Ring Harness Hardware Ankle Booties

Kork-Ease Elsbury Leather Chelsea O-Ring Harness Hardware Ankle Booties

Permanently Reduced

Vivette Suede Buckle Hardware Strap Ankle Booties

Vivette Suede Buckle Hardware Strap Ankle Booties

Vionic Vivette Suede Buckle Hardware Strap Ankle Booties

Permanently Reduced

Optimus Stud Leather Hardware Ankle Booties

Optimus Stud Leather Hardware Ankle Booties

Naturalizer Optimus Stud Leather Hardware Ankle Booties

Permanently Reduced

Mitzi Leather Booties

Mitzi Leather Booties

Johnston & Murphy Mitzi Leather Booties

Permanently Reduced

Shaelynn Leather Western Booties

Shaelynn Leather Western Booties

Sofft Shaelynn Leather Western Booties

Beatrice Waterproof Leather Booties

Beatrice Waterproof Leather Booties

Sofft Beatrice Waterproof Leather Booties

Yoyo Suede Booties

Yoyo Suede Booties

Naturalizer Yoyo Suede Booties

Permanently Reduced

Calafat Leather Croco Embossed Leather Booties

Calafat Leather Croco Embossed Leather Booties

Pikolinos Calafat Leather Croco Embossed Leather Booties

Women's Rangeley Pac Winter Ankle Booties

Women's Rangeley Pac Winter Ankle Booties

L.L.Bean Women's Rangeley Pac Winter Ankle Booties

Only size 10, 6 available

Optimus Studded Suede Hardware Ankle Booties

Optimus Studded Suede Hardware Ankle Booties

Naturalizer Optimus Studded Suede Hardware Ankle Booties

Permanently Reduced

Taj Suede Booties

Taj Suede Booties

Born Taj Suede Booties

Permanently Reduced

Adriana Perforated Suede Booties

Adriana Perforated Suede Booties

Sofft Adriana Perforated Suede Booties

Permanently Reduced

Now $63.00 - $120.60

Niobe Etched Leather Studded Ankle Booties

Niobe Etched Leather Studded Ankle Booties

L'ARTISTE Niobe Etched Leather Studded Ankle Booties

Internet Exclusive

Only size 41(9.5, 10) available

Men's Matias Leather Ankle Boots

Men's Matias Leather Ankle Boots

Dune London Men's Matias Leather Ankle Boots

Internet Exclusive

Llanes Zip Leather Booties

Llanes Zip Leather Booties

Pikolinos Llanes Zip Leather Booties

Melinda 30 Leather Chelsea Booties

Melinda 30 Leather Chelsea Booties

Josef Seibel Melinda 30 Leather Chelsea Booties

Permanently Reduced

Kaylee Leather and Plaid Chelsea Booties

Kaylee Leather and Plaid Chelsea Booties

Aetrex Kaylee Leather and Plaid Chelsea Booties

The Lucky Boot Leather Western Booties

The Lucky Boot Leather Western Booties

Besita Boots The Lucky Boot Leather Western Booties

Optimus Leather D-Ring Hardware Ankle Booties

Optimus Leather D-Ring Hardware Ankle Booties

Naturalizer Optimus Leather D-Ring Hardware Ankle Booties

Permanently Reduced

Yoyo Leather Booties

Yoyo Leather Booties

Naturalizer Yoyo Leather Booties

Permanently Reduced

Sigourney Leather Booties

Sigourney Leather Booties

Dansko Sigourney Leather Booties

Permanently Reduced

Women's Anistone Suede O-Ring Harness Hardware Biker Booties

Women's Anistone Suede O-Ring Harness Hardware Biker Booties

Dr. Martens Women's Anistone Suede O-Ring Harness Hardware Biker Booties

Permanently Reduced

Soft 7 Tred Nubuck Booties

Soft 7 Tred Nubuck Booties

ECCO Soft 7 Tred Nubuck Booties

Save on Select Items

Now $97.50 - $195.00

Beckie II Ruched Leather Zip Booties

Beckie II Ruched Leather Zip Booties

Sofft Beckie II Ruched Leather Zip Booties

Permanently Reduced

Migyn Suede Double Buckle Moto Booties

Lucky Brand Migyn Suede Double Buckle Moto Booties

Permanently Reduced

Men's Vigo Leather Lace Up Zip Ankle Boots

Men's Vigo Leather Lace Up Zip Ankle Boots

Pikolinos Men's Vigo Leather Lace Up Zip Ankle Boots

Mini Crave Leather Buckle Strap Hardware Ankle Booties

Mini Crave Leather Buckle Strap Hardware Ankle Booties

Taos Footwear Mini Crave Leather Buckle Strap Hardware Ankle Booties

Classic Mini II Suede Water Resistant Family Matching Ankle Booties

Classic Mini II Suede Water Resistant Family Matching Ankle Booties

See all 6 colors

UGG Classic Mini II Suede Water Resistant Family Matching Ankle Booties

Save on Select Items

Now $85.00 - $170.00

Roan Spry Leather Engineer Booties

Roan Spry Leather Engineer Booties

Bed Stu Roan Spry Leather Engineer Booties

Beckie II Ruched Suede Zip Booties

Beckie II Ruched Suede Zip Booties

Sofft Beckie II Ruched Suede Zip Booties

Permanently Reduced

134 Items
1
2
Next Page
Last

About Comfortable Ankle Boots

Discover the perfect blend of style and comfort with our collection of comfortable ankle boots. Designed for all-day wear, these boots feature cushioned insoles and supportive structures that keep your feet feeling great, whether you're running errands or enjoying a night out. With a variety of materials and styles, you can find the ideal pair to match any outfit.

Our comfortable ankle boots come in various designs, including classic leather, soft suede, and trendy chukka styles. Each pair is crafted with attention to detail, ensuring durability and a fashionable look that transitions seamlessly from season to season.

What makes ankle boots comfortable?

Comfortable ankle boots typically feature cushioned insoles, arch support, and flexible outsoles that provide ease of movement. These elements work together to reduce foot fatigue, making them suitable for extended wear.

Can comfortable ankle boots be worn for all occasions?

Yes, comfortable ankle boots are versatile enough to be worn for various occasions, from casual outings to more formal events. Their stylish designs allow them to complement a wide range of outfits, making them a wardrobe staple.

Are comfortable ankle boots suitable for wide feet?

Many comfortable ankle boots are designed with wider toe boxes and adjustable features, making them suitable for individuals with wide feet. It's essential to check the sizing and fit specifications to ensure the best comfort.

What materials are best for comfortable ankle boots?

Common materials for comfortable ankle boots include leather, suede, and synthetic fabrics. Each material offers different benefits, such as breathability, durability, and ease of maintenance, allowing you to choose based on your preferences.

How do I style comfortable ankle boots?

Comfortable ankle boots can be styled in numerous ways. Pair them with jeans, skirts, or dresses for a chic look, or wear them with tailored pants for a polished appearance. Accessorizing with scarves or statement jewelry can elevate your outfit further.

Are comfortable ankle boots good for walking?

Many comfortable ankle boots are designed with features that make them suitable for walking, such as cushioned insoles and supportive soles. However, it's important to choose a pair specifically designed for comfort and support if you plan to walk for extended periods.

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

***