Of all the fall staples we gravitate toward year after year, none seem to be quite as popular as ankle boots with heels. Whether you typically dress in head-to-toe athleisure or like to opt for complete minimalism, these boots transcend all levels of personal style. With the variety of styles that come each season, this is one shoe that will never feel old—we promise.
Whether you decide to make them part of your daily fall uniform or you want a chic pair to wear on your next night out, we guarantee you’ll want to wear a pair of heeled ankle boots for more occasions than one within the coming months and beyond. Ahead, we’ve rounded up our favorite heeled ankle boots that will elevate any of your outfits this fall. From comfortable thick heeled boots to stiletto options, there's an option for everyone. Check them all out below.
I love the subtle print on this.
This has the perfect Western flair.
Just wow.
This is a great affordable option.
I'm intrigued by these.
Chic yet comfortable.
Fellow editor Anna LaPlaca speaks very highly of Vagabond's shoes.
Staud makes our favorite handbags, but its shoe game is just as good.
These will be an everyday staple.
A controversial favorite from the fashion set.
The low heels and slim, sleek shape make these great for walking around.
Can you believe these are Zara?
Dream boots.
If you're more into a comfortable and chunky heel.
If you like a pointed toe.
Animal print is always a good idea. It'll add a statement to any simple outfit.
A great under-$100 option that looks much more expensive than it is.
Sock boots are trending again.
Like chocolate.
Chelsea boots are a forever classic.
Don't sleep on Mango's shoe variety.
These are on crazy sale.
These boots are best sellers for a reason.
We've never seen a Chelsea boot look so luxe. Leave it to suede.
Next: These Are the 8 Biggest Fall 2021 Shoe Trends, Period
-
The Brutally Honest Skincare Advice You Needed to Know Yesterday, According to 2 Beauty Industry VetsThe Dieux founders share their hot takes and unfiltered product recs.
-
Sorry to My Classic Black Shoes, But This Printed Shoe Trend Is Defining Fall 2025Spotted on fashion people in Venice, NYC, and Copenhagen.
-
Hold the Sandals—This Is the Shoe Trend to Wear With Dresses in SeptemberAs seen on Alexa Chung.
-
Move Over, Jelly Shoes—I Predict *This* Chunky Shoe Trend Will Be Everywhere Come FallGen Z discovers boho chic.
-
If You Want Prettier Outfits, Swap Black Pumps for This Dated ColorEven Serena Williams is making the switch.
-
This Simple Fashion Person–Approved Layering Technique Changed the Way I Wear My BasicsEffortlessly cool.
-
This Is the "Dated" Heel Trend to Buy Instead of Basic Pumps If You Want Cooler Outfits This FallSophie Turner is making the switch.
-
Hailey Bieber Just Said This Classic Print Looks So 2025 When Paired With This Unconventional Shoe ColorUnexpected, yet so chic.
-
Forget Mules—*These* Are the Classic Anti-Flats L.A. It Girls Wear for Dinner at Giorgio BaldiGood food, great footwear.
-
FYI: Every Fashion Person Is Buying This Pretty Shoe Color Instead of Black Right NowCount us in.
