How to Wear Ankle Boots the Right Way

One of the hottest shoe trends of the season is the ankle boot. Versatile, chic, and timeless, ankle boots add a pinch of posh to any look you wear this fall. Whether you’re a jeans-and-chunky-sweater type, a dress-and-leggings lover, or some combination of the two, you can rock ankle boots and create a flawless head-to-toe look.

If you’re like me, you scour the internet for images that are as inspiring as they are enticing. That means sometimes I’ll come across something and think, Hmmm, would I wear this? Chances are you can pull anything off if you know how to wear it. Here, nine killer looks that make ankle boots the star of the show—and how to pull them off.

With a Cozy Cape

What better way to welcome fall than with an outfit that keeps you cozy on days that aren’t quite cold enough for a coat yet require some layers? The voluminous top balances the short boots perfectly, preventing the look from being too over the top and keeping the focus in equilibrium—the top is eye-catching, but so are the sassy, metal-toned boots. Get the look with a pair of Topshop Martini Block Heel Booties ($135).

Image Credit: Instagram @anabelmaldonado

RELATED: 9 Comfortable Pairs of Boots You Need This Fall

With a Cropped Jacket

yellow cropped jacket black ankle boots skinny jeans

If ever you’re in need of a quick, no-fuss, no-fail ensemble, try this. A pair of flattering skinny jeans paired with a hip-length blouse is classic. Throw a cropped jacket on top and finish with a pair of ankle boots that lend the look a hint of edge. For a similar look, try Lucky Brand Boide Booties ($129).

Image Credit: Instagram

With Short Shorts

ankle boots with short shorts and black tights

Who wears short shorts? You do—even in the fall. It’s easy to make this look work when you wear those bottoms with cozy tights (think opaque and dark), along with a pair of ankle boots. Longer boots run the risk of looking a bit costume-like, while this is more streamlined and even a touch rocker chic. These G by GUESS Fella Combat Boots ($59.95) are a great match.

Image Credit: Instagram @dreamersgo_

With Classic Denim

beige ankle boots with rolled up skinny jeans

Did someone say classic? If you normally wear jeans and sweaters with ballet flats or black motorcycle boots, switch it up and slip into a pair of taupe boots. Buckle accents and a short wooden heel toughen them up a bit, but the effect is overall rustic chic. These Mossimo Supply Co. Jessica Genuine Suede Strappy Boots ($49.99) fit the bill nicely.

Image Credit: Instagram @derekjohnsonphotos

With a Pop of Color

blue suede ankle boots with blue jacket and red tights

One of the great traits of the ankle boot is its small shaft, which means you can rock a bright hue that you probably wouldn’t be able to comfortably wear in a taller silhouette. This look works because it pairs like colors, with a little something to break it up in the middle. And the teal hue is completely fresh and unexpected. Try O’Neill Taylor Jade Suede Knotted Ankle Boots ($76) for a similar take on the look.

Image Credit: Instagram @style_of_strangers

With a Midi Skirt


The midi skirt was once a casual trend, but it’s cemented a permanent place in women’s wardrobes everywhere. It looks a bit twee and dainty with heels or flats, but ankle boots take it in a better direction—more approachable and perfect for cooler weather. The contrasting neutrals on these Patricia Green Chantel Foldover Booties ($290) make them a versatile match for almost any midi skirt or dress.

Image Credit: Instagram

With Colorful Pants

burgundy jeans with brown ankle boots

Fall is a great time to rock a pair of vivid pants in one of the season’s hottest colors—think wine, purple, or navy. When you pair them with an airy blouse and neutral ankle boots, you’re really in business. The boots are understated enough to let the pants stand out. These Doucal’s Ankle Boots ($137) offer the same faded leather material.

Image Credit: Instagram @jess.sev

With Boyfriend Jeans

black ankle boots boyfriend jeans lacy camisole

This is a no-brainer. Boyfriend jeans are baggy, relaxed, and perfect whether you’re headed out on the town or running errands. Since they’re folded at the ankle, they’re perfect for wearing with a pair of short boots. The Apt. 9 Zipper Ankle Boots ($39.99) are a great choice—wear them with a lighter shade of denim, a white tee, and a sweater or jacket for an instantly pulled together fall ensemble.

Image Credit: Instagram @frankvinyl

With Lots of Layers

black pointy ankle boots with leather jacket and cropped pants

It’s fall, when the keyword is layers—lots and lots of them. If you’re wearing something like this outfit, which features a cropped leather jacket over a plaid flannel shirt over a white tee, plus a pair of black cropped pants, you almost can’t wear anything but ankle boots. Since they hit your ankle, they’ll help negotiate that space between your pants’ hemline and the top of the boot. They also look right at home with all that cold-weather attire. The sharp toe and no-fuss black leather on these Nine West Jaison Booties ($139.95) make them a smart pick.

Image Credit: Instagram @tmarkova_

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