11 Cute Ankle-Boot Outfits That Are Anything But Basic

Ah, ankle boots—that perennially stylish wardrobe staple that you return to time and again whenever the temperature outside starts to drop. Even though knee-high styles may be making their way back into the market, I won't be getting rid of my beloved short boots anytime soon. But as much as I love my timeless ankle-hugging friends, it can be a little challenging to change up the outfit game when it comes to styling because there are only so many times you can wear them with a sweater and a pair of jeans.

To that end, I've scoured Instagram to find those who gave the footwear silhouette stylish spins for some outfit inspiration this season. Whether they're sporting it under slip dresses or bringing their casual sweater outfits to new heights, leave it to our favorite fashion girls to teach us styling lessons on wearing the ankle boots we all have in our closets.

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(Image credit: @itsmekellieb)

Wear your dresses into the colder temperatures by pairing them with stockings and your trusty pair of black leather booties.

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(Image credit: @smythsisters)

Trench coat + neutral base + black ankle boots = a classic and forward outfit formula.

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(Image credit: @noore )

I love a matching knit set because there really is no limit when it comes to layering.

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(Image credit: @greceghanem)

Add a chic element to your loungewear with a pair of cream-colored ankle boots.

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(Image credit: @fiahamelijnck)

When in doubt, pairing your ankle boots with a brightly hued puffer coat is always a great call. 

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(Image credit: @jen_wonders)

You can't go wrong with a blazer, denim, and ankle boots.

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(Image credit: @champagnemani)

Who said you can't bring your tennis skirts into the colder months?

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(Image credit: @trustmebuythis)

Puffer season is among us.

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(Image credit: @madelynnfurlong)

A jumpsuit is a one-stop outfit that pairs so well with ankle boots.

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(Image credit: @oliviafaeh)

When in doubt, throw on a pair of ankle boots and a sweaterdress, and you'll be good to go. 

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(Image credit: @camillecharriere)

Wear animal-printed boots to add a pop to an otherwise minimal ensemble.

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This post was originally published at an earlier date and has since been updated. Up next, These 10 Winter Boot Trends Are Starting to Feel Dated, so We're Replacing Them

Associate Fashion Editor
Yusra Siddiqui is an editor who resides in New Jersey but bounces between the suburbs and NYC. (She's a Jersey girl at heart.) After interning at Who What Wear in 2019, she found her way to the team after graduating from LIM College in 2022 with a fashion media degree. She's also spent time writing and working for publications such as Fashionista, Coveteur, and Nylon, but she always knew that Who What Wear was where she was meant to be. When she's on the job, she's perusing runway shows, analyzing the latest thing fellow Gen Zers are up to on the internet, and sharing what she can about the modest-fashion market. You can also catch her dabbling in entertainment, talking about the costume choices of the latest Netflix series or diving deeper into how the plotline affects the viewers in a myriad of ways. Lastly, she likes to create content for Who What Wear's TikTok. Her personal time is spent doing similar but also different things—deep diving into almost every new TV show (Bridgerton, Gilmore Girls, and Stranger Things are favorites), planning her next local getaway (whenever that may be), and reading the latest Emily Henry or Sally Rooney novel in one sitting.