How to Wear Ankle Boots for All Occasions

Whether you call them ankle boots or booties, they're undoubtedly one of the cutest footwear styles for women. And believe it or not, heeled booties are more versatile than you may think.

If you adore the look of ankle booties but don't know how to style them, you've come to the right place. Read on for ideas and insight into how to wear ankle boots for every occasion.

How to Style Ankle Boots: 6 Ways

There are virtually endless ensembles you can wear with heeled booties. This women's wardrobe staple boasts the practicality of traditional boots, the elegance of fancy footwear, and the sportiness of sneakers. Needless to say, it's the best of all worlds.

No matter where you're headed or what you're doing, there's a pair of booties for women that fit the occasion. Below, how to style ankle boots six different ways.

1. Enjoy Yourself in Jeans

Wondering how to wear ankle boots with jeans? We got you. Specific cuts come and go, but the fact of the matter is that jeans are always in style. Though denim is undeniably seasonless, jeans and ankle boots are one of our favorite looks for fall and winter. 

And believe it or not, boot-cut jeans aren't your only option. Whether you're partial to skinny jeans, wide-leg, boyfriend jeans, flared, high-rise, cropped, or relaxed, you've got tons of styling possibilities for outfits with booties.

Besides the cut, different denim washes are better suited for certain occasions. For instance, black and dark-wash boyfriend jeans can be dressed up, distressed denim is more casual, and white is a great pick for the warmer seasons.

When dressing for the fall and winter, however, opt for an oversized sweater, a flannel button-down, or a flowy shirt with form-fitting jeans. If you're slipping into a looser pair, go with a fitted top to balance out your look.

What Ankle Boots Go With Jeans?

Most styles can be paired with jeans. That said, we appreciate the laid-back appeal of slip-on sneaker booties and love a block-heel ankle boot for a more polished look.

2. Show Some Ankle in Cropped Trousers

Ankle boots, as the name implies, draw attention to the ankles. With this in mind, why not show off your lowermost leg with a pair of cropped trousers or leather pants?

Wide-leg, tapered, pleated, high-waisted, fit-and-flare, you name it—almost any style of pants will do. The most crucial thing is finding a cut that's not too low or too high, as you'll want to show 3 to 5 inches of exposed skin without covering the tops of your heeled ankle boots.

Fitted trousers look chic with both tight and loose tops. But similar to jeans, relaxed fits go great with slightly tighter shirts, such as a bodysuit, to avoid a frumpy look.

What Ankle Boots Go With Cropped Trousers?

For a sophisticated vibe, reach for low ankle booties with leather pants. If you want a little extra height, block-heel boots are an excellent choice as well for heeled ankle boots.

3. Dress for Success in a Skirt

Can't figure out how to style ankle boots for work or special occasions? Consider slipping into a midi skirt. Booties work well with flowy, pleated, pencil, A-line, and asymmetrical skirts. Midi cuts are ideal, as they're professional while also allowing you to show off your shoes.

On top, we recommend a blouse, fitted tee, mock-neck, bodysuit, or another style that can be tucked in to your midi skirt or other style of skirt. Finish the look with a slouchy sweater, leather jacket, blazer, or a warmer coat if needed.

What Ankle Boots Go With Skirts?

Offering a put-together yet practical appeal, stacked-heel ankle boots are perfect for skirts. Leather or suede low-heel booties are a solid option, too.

4. Master the Maxi Dress

Maxi dresses are flattering on all figures, plus they're seasonless, comfortable, and can be dressed up or down. As with trousers, the key to wearing a full-length dress with ankle boots is to find one that's not too long.

With this in mind, look for a style that sits just above your ankles. Dresses with slits or asymmetrical cuts can also work. For this outfit, we love cropped outerwear, such as a denim jacket or bomber.

What Ankle Boots Go With Maxi Dresses?

Wedges are arguably the best type of shoe to wear with a maxi dress. They're semi-dressy, comfortable, supportive, and easy to walk in—what's not to love? But instead of espadrilles or sandals, go with wedge booties.

5. Lean in With Leggings

Leggings and ankle boots are among our favorite contemporary looks for women. This casual combo has been a go-to for several years and shows no signs of fading out of style.

Since leggings are form-fitting, we recommend wearing them with a long, loose-fitting top. This could be an oversized cardigan, a slouchy cable-knit sweater, a drapey blouse, or an extra-long button-up shirt.

What Ankle Boots Go With Leggings?

You can't go wrong with Chelsea boots and leggings—we're big fans of chunkier heels with lugged outsoles. If the forecast is wet weather, look for a water-resistant pair.

6. Opt for Laid-Back Athleisure

Once criticized as underdressing in public and considered a passing trend, athleisure now holds a permanent place in modern fashion. And sneakers aren't your only footwear option.

From yoga pants and running tights to crewneck sweatshirts and half-zip jackets to crop-tops, performance tanks, and jogger sets, athleisure wear is everything we love about casually comfy apparel.

Whether you prefer an all-black look or like to mix and match colors and patterns, ankle boots are an excellent choice. To tie everything together, throw on a hat or beanie.

What Ankle Boots Go With Athleisure?

Combat-style ankle boots with thick lugs balance out sporty athleisure with an edgy appeal. Plus, weather-resistant styles can make your outfit ready for the rainy season. But if you prefer a head-to-toe active look, go with sneaker booties.

How to Wear Ankle Boots: 3 Tips

As you can see, there's a wide range of pieces you can wear with ankle boots—many of which are probably already in your closet. Want more tips? Here's what we recommend for nailing your outfit.

1. Consider Color

It's good to have at least one pair of neutral booties in your wardrobe. Black, brown, camel, taupe, grey, and white are not only seasonless but also go with virtually anything. That said, olive green, animal print, and camo are also surprisingly versatile, not to mention super stylish.

2. Show Some Ankle

As noted above, booties look best when the entire silhouette is visible. Whether you're rocking jeans, trousers, a skirt, a dress, leggings, or athleisure, look for a cut that doesn't cover your boots. In the end, this will make your ensemble look more intentional while helping you avoid a bunched-up hem.

3. Weather-Proof Your Boots

Weather-treating your shoes might not be the first thing you think of when styling a look. However, the peace of mind that comes with knowing your booties won't get ruined by precipitation presents you with a lot more outfit options. It'll also help preserve your footwear, so you can keep wearing your favorite pair season after season.

Get a water-repellent shoe care spray formulated specifically for the upper material. Coat the uppers evenly and let your boots dry completely before putting them on. Some ankle boots, including styles you'll find from TOMS, come with water-resistant uppers—though it doesn't hurt to re-treat them every few months.

Women's Ankle Boots from TOMS

Now that you know how to wear ankle boots, you can put your best foot forward and make each outfit your own. TOMS carries an impressive range of boots for women, including block-heel booties, stacked-heel boots, Chelsea boots, sneaker booties, combat-style boots, and wedge booties.

The uppers are made of high-quality materials, like leather, suede, and nubuck, and the built-in OrthoLite® Eco X40 Hybrid insoles offer long-term cushioning. Whether with pull tabs, gore panels, zippers, or laces, our boots are easy to get on and off. TPR outsoles offer optimal traction when the ground is slick, and many of our styles have water-resistant uppers.

Shop the women's boots and booties collection today!



Reviewed By Kendall Pilgrim 

Kendall Pilgrim is an LA-based writer and editor determined to go all the places and see all the things. She’s been operating in the footwear space for 3 years, writing about the latest trends or styles and helping brands make bold statements through innovative copy.