Learn how to wear booties with every on-trend outfit this fall.

By Savannah James
Updated September 18, 2019
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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 bloggers who 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.

The cropped hemline on these jeans creates a frame for showing off your favorite booties. Pair the look with an oversized sweater for a casual fall ensemble that still looks polished.

Cropped jeans and ankle boots are a match made in heaven. Make sure your booties have a pop of color if you want to add an extra element of style to your denim outfit.

If you’re going for a really casual look, wear brown ankle boots with cuffed jeans for a relaxed vibe. Finish off the look with a cozy sweater and you have the ideal outfit for fall’s chilly weather.

Embellished hem jeans look great with a pair of booties that fit your foot more like a sock than a loose boot. The matte finish on these makes them very versatile; they can easily be dressed up or down depending on the rest of your outfit.

Wear your wide leg jeans with ankle boots that have a block heel, to ensure comfort all day long.

How to Wear Booties With Dress Pants or Cropped Pants

If you’re wondering how to wear booties with pants that aren’t jeans, look no further. 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 one of these outfits a whirl.

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).

These ultra-cropped culottes go perfectly with short black booties. The color palette in this outfit feels appropriate to fall; moody hues like burgundy and black are a great combination for the season.

If you’re seeking inspiration for wearing ankle boots to work, check out this style. Comfortable, wide-leg cropped pants with a tucked-in blouse—complete with embellished sleeves—will look and feel great in the office. These ankle boots are stylish without being overstated, with a low enough heel to make sure your feet are comfortable all day long.

Who says dress pants have to be boring? Try tucking them into ankle boots for an ultra stylish look that works just as well during the week 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 what 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 brown boots make for a great style combination. For a laid-back look like this, opt for flat ankle boots, or rock a heel for added height

Wear your favorite floral midi dress with black ankle booties for a fall-ready outfit that easily transitions from day to night.

A fringed skirt deserves a fun pair of ankle boots to go with it. These statement boots go well with a statement skirt, without coming off as too overpowering (talk about a style star!).

A maxi dress can have a major impact with the right bootie peeping out from beneath the fabric. Consider a black zip-up bootie, like the one pictured below, for a sleek, cool-girl vibe.

How to Wear Ankle Boots With Leggings

Ankle boots with leggings is a classic combination that never seems to go out of style. No matter what the weather is like, this is a great way to create a comfortable and attractive outfit.

These loose leggings look like they were made to be worn with a stiletto ankle boot. The classic colors in this outfit come together for a look that works for going to the airport or running errands, all while looking incredibly pulled together.

The wide ankle opening on these booties is seriously flattering with a pair of figure-hugging leggings. Wear this combination with an oversized turtleneck for an effortless look for apple-picking or sipping cider by the fire.

If you’re looking to wear your ankle boots with leggings in a more dressed up setting, consider tossing on a pair of faux-leather leggings. Add a pop of color with your boot and—voila!—you have a look that can take you anywhere.

Embellished booties are a smart way to elevate a simple ensemble of leggings and a sweater. Take this look one step further by adding a scarf tied just so (and be prepared to have a comfortable outfit that warrants at least one Instagram photo!).