How to Wear Ankle Boots Fashionably

When summer comes to a close, we’re always a little bummed. However, we tend to perk back up upon remembering the joys of fall fashion. One of our favorite autumn staples is booties for women. Ankle booties, boots—whatever you want to call them, they’re arguably the cutest and most versatile shoe style of the season.

If you love the look of a short, heeled boot but aren’t quite sure how to wear booties this fall, you’re in good hands. The footwear enthusiasts at Vionic are here to provide our expertise on every ankle boot style. Whether you’re looking for a fall staple for a night out or the perfect flat ankle boot for everyday wear, these ankle boot styles are sure to elevate your wardrobe with comfort, versatility, and effortless fall style. Keep reading to find out what to wear with ankle boots.

How to Wear Booties: Dos and Don’ts

Ankle booties for women offer virtually endless styling possibilities. They can be dressed up or down and worn with professional or casual outfits. With the practicality of a traditional boot and the polished appearance of a dressy boot, ankle boots really are the perfect winter shoes for women. Find the dos and don’ts of how to wear these stylish boots for women below.

Do Wear Cropped Pants

Booties flatter the ankle, and they’re meant to be shown off. That’s why one of the best ways to style them is with a cropped pant or cuffed jeans. We love the look of high-waisted cropped pants or straight leg trousers with an ankle boot. The key is to find a cut that’s not too high or low. Ideally, you’ll want to show off about 2 to 5 inches of skin.

For your top, the right fit depends on your cropped pants. With looser or relaxed-fit trousers, opt for a slim-cut shirt. With skinny jeans and other tight styles, go for a drapey blouse or a long button-down shirt. For outerwear, throw on a trench or pea coat.

Don’t Be Afraid to Wear Skirts or Dresses

If you’re waffling about what to wear with ankle boots, don’t be afraid to rock skirts or dresses. In fact, if any boot style goes with skirts and dresses, it’s booties. Any length will work too. Whether you’re partial to a maxi dress, midi skirt, sweater dress, pencil skirt, shift dress, or short skirt, a pair of ankle boots can look really flattering. They really are the best shoes to wear with dresses during the fall! You can’t go wrong, just balance the proportions, pick a boot height that complements your hemline, and you’ve mastered how to wear a dress with boots in the chicest way.

As with skirts, looser skirts should be styled with slim-fit tops, and tighter styles can be paired with more relaxed shirts or sweaters. For shorter hemlines, you might consider tights. When wearing a skirt or dress with booties, we adore the look of a leather jacket or denim coat on top. Finish the look with a cute cross-body bag and your favorite jewelry. Pairing ankle boots with a maxi skirt or midi dress truly is one of the best ways to wear ankle boots.

Do Opt for Jeans

Jeans and ankle boots go hand-in-hand in the fall and winter. And while many consider jeans and heels to be a fashion faux pas, one exception is heeled booties. Not sure how to wear jeans with booties? Whether you prefer a black skinny jean, straight leg jeans, cuffed jeans, flared jeans, mom jeans, or boyfriend jeans, we recommend a cropped cut. A cropped jean will slim your ankles and showcase your shoes.

As for your top, you’ve got tons of options. Consider an oversized knit sweater for a comfy-cozy look or a button-down blouse for a more elegant aesthetic. Flannel shirts are another fall staple, and they always pair well with straight jeans. For a dressier look, a long blazer can be perfect for outerwear. But we also love bomber jackets and utility jackets for a more laid-back appeal. If you want to keep your feet warm in winter, opt for jeans long enough to cover your ankle and pair them with thicker, cozy socks to seal in the warmth.

Don’t Count Out Leggings

Booties and leggings are one of our favorite contemporary outfit combos if you’re going for a comfy and casual look. The look has been a go-to for women for many years now and doesn’t appear to be going out of style any time soon. It’s comfy, practical, cozy, and chic—and there are many routes you can take to make it your own.

Since leggings are tight and stretchy, we suggest pairing them with a loose-fitting cable-knit sweater, a long cardigan, a drapey blouse, or an oversize sweatshirt. For outerwear, a classic raincoat can be a cute and practical outfit idea to pair with either black or brown ankle boots. If wet weather isn’t on the forecast, throw on a black leather jacket, a pea coat, or a utility jacket.

Do Consider Color

One thing to keep in mind when styling heeled ankle boots is color. Neutral hues like black, brown, taupe, tan, grey, and white go with almost anything. However, leopard and snake print can also be surprisingly versatile, not to mention fashion-forward.

We suggest having at least one neutral pair of booties in your arsenal. That way, you’ll always have something to fall back on. One of our favorite timeless ankle boot styles is the Savannah Heeled Ankle Bootie, polished enough for the office yet chic enough for a night out. For something equally sophisticated, the Vynn Heeled Ankle Bootie is a true classic that never goes out of style, making it a smart, forever addition to your fall wardrobe.

Do Show Off Your Boots

As we mentioned, booties show off your ankles, and they look best when you return the favor. In other words, try to find pants, jeans, dresses, and skirts that don’t cover your boots. This will make your outfit look more pulled-together and intentional. Plus, you’ll avoid bunching up your pants, which can be unflattering on the ankles and throw off your ensemble.

Don’t Ruin a Good Pair of Booties in the Rain

Our next piece of advice is less about styling and more about preserving your footwear. When you slip on a pair of ankle boots, it can give you a false sense of security when stepping out into the rain. Unless they’re treated for wet weather, booties are just as susceptible to water damage as regular shoes.

With that said, if you want to rock a pair of ankle boots when it’s raining, Vionic has you covered. Our water resistant shoes for women include several different types of boots. We even carry water-resistant heeled ankle boots for when fancy occasions fall on rainy days. Learn how to style your booties for every season and get tips on how to waterproof your shoes to ensure they withstand rain and other weather conditions. Stay fashionable and prepared, no matter the forecast!

Do Invest in a Good Pair of Booties

As we said, booties show no signs of going out of style, so it’s definitely worth investing in a good pair. High-quality styles will last you through the chilly season and for years to come. The boots and booties from Vionic have durable outsoles and suede or leather uppers that are made to last. And most of our designs are the perfect balance of neutral and fashionable, so you won’t have to worry about them going out of style.

Don’t Overthink It

If you’re ever stuck on what to wear with booties, our best piece of advice is to not overthink it. The rules of fashion are always evolving, and they’ve become a lot more lax over the years. The truth is, there are no rules.

What styles stand out to you? What do you feel like your best self in? Do you like eclectic clothing, vintage pieces, or athleisure? Lean into it! Go with what you love, and strut your stuff with confidence.

Fashion-Forward Ankle Boots and Booties from Vionic

A comfy ankle boot is a must-have during the fall and winter. But believe it or not, you can actually wear booties year-round. With this in mind, the seasonless styles from Vionic are designed to put the finishing touch on virtually any ensemble. Each pair can be styled with jeans, pants, leggings, skirts, dresses, or anything else you have in mind.

From western-style boots, sock booties, almond-toe booties, and flat ankle boots to riding boots, sneaker booties, metallic boots, snakeskin booties, and block heel styles, we have it all. And if you need a weather-resistant pair, we have those too. And for the days when you want to elevate your look even more, we also offer tall boots that bring extra warmth and effortless winter polish.

When you feel good, you look good. Vionic offers styles leading in both comfort and fit. Each pair from the collection has our exclusive Vio Motion Support technology. This means podiatrist-designed orthotics are built right into the soles, providing you with the arch support, heel stability, and cushioning you crave.

Wondering “how should boots fit?” Our size guide can help you determine your Vionic shoe size. From there, you can browse boots and booties for women to find your perfect pair.