Fall outfit inspiration that'll show you how to wear women's ankle boots with any look.

By Savannah James and Real Simple Editors
Updated November 19, 2020

Ankle boots—or booties—are arguably the ultimate fall shoe. With so many different options (heeled ankle boots and white ankle boots included), it’s often difficult to get out of the rut of wearing the same tried-and-true pair of shoes with the same tired outfits week after week. But don’t worry—we’ve found some fresh new ideas on how to wear booties with jeans, pants, dresses, skirts, and every wardrobe essential in between. Looking for fall outfit inspiration? Look no further than these style combinations that make women's ankle boots look oh-so-chic.

How to Wear Booties With Jeans


Wearing ankle boots with jeans is a great way to ease into the bootie trend if you’re just not sure what to pair them with. Whether you are dressing your jeans up or down, there are different types of ankle boots you can wear to stylishly assist in the process.

Cropped jeans and ankle boots are a match made in heaven. Cuff the hems—instead of tucking them into the boots—for some major ankle action. The cropped hemline creates a frame for showing off your favorite booties. If you’re going for a really casual look, wear brown ankle boots with cuffed jeans for a relaxed vibe. If you want to add an extra element of style to your denim outfit, make sure your booties have a pop of color. Finally, pair the look with an oversized sweater for a casual fall ensemble that still looks polished.

How to Wear Booties With Dress Pants or Cropped Pants


Ankle boots look just as great with dress pants and cropped trousers as they do with denim, so step outside of your comfort zone and give the style a whirl. Patterned boots and chunky jewelry add a bit of edge to paper bag-waist pants and a slouchy, off-the-shoulder pullover. Cropped flares ensure that your ankle boots stand out, while a slight heel gives you a little boost (so even if your legs are on the shorter side, the cropped pants will still be flattering).

The color palette in this outfit feels appropriate to fall; moody hues like beige and black are a great neutral combination for the season. Try tucking your pants into ankle boots for an ultra stylish look that works just as well at work as it does on the weekend.

How to Wear Booties With a Dress or Skirt


Ankle boots can also look incredibly stylish when worn with a dress or a skirt, no matter the length. Whether you’re rocking a maxi skirt on the weekend or sporting a midi dress to work, there is an ankle boot that will work with your outfit.

This neutral sweater dress and versatile black boots make for a great style combination. Play with texture by mixing a jewel-tone velvet skirt with studded booties and a bucket bag. A chic high-low turtleneck streamlines the look. A maxi dress can also have a major impact with the right bootie peeping out from beneath the fabric. Consider a black zip-up bootie, like the one pictured above, for a sleek, cool-girl vibe.