9 Ankle Boot Outfits That Take the Style in Every Direction

This just may be the hardest-working shoe in your closet.

Brother Vellies Lauryn ankle boots in cow print


In an effort to make more conscious shopping choices, wearability is always a top priority. How often and how differently can we style one piece? How many occasions can one silhouette work for? And as far shoes go, ankle boots are often the item that seems to adapt to almost anything. While not all booties serve the same purpose, the ankle height lends itself to endless styling possibilities with trousers and jeans—cropped and floor-length alike—and dresses for both casual and more formal settings. 

Ahead, we offer a sampling of these ankle boot outfits with many of the season’s latest styles accounted for, including kitten heels, block heels, and lug soles that lend sleek durability to any look. Consider these ensembles a bit of inspiration as you consider a future footwear investment or even craft new looks with pieces you may already own. Long story short: Your ankle boots are your hardest-working shoes, as long as you know what to pair them with. See nine looks to try below.

Treaded Soles and Mini Dress

A check-print mini dress, a cherry-colored jacket, and a puffer shoulder bag combine to create a sweet and playful aesthetic. However, this look really feels complete thanks to the look of heavy treaded soles on these slip-on ankle boots.

Chelsea Boots and Straight-Leg Denim

Chelsea boots are a cold-weather staple, complementing an endless number of outfits. For a classic approach, pair them with clean-cut, straight-leg denim, a shirt with a statement collar, and abstract hoops for a unique finishing touch.

Square-Toe Boots and Classic Trousers

The ‘90s-inspired square-toe bootie looks beautiful with classic black trousers, another closet essential. Add a few winter layers and take this ankle boot outfit to the office, dinner, or anywhere else that calls for a polished ensemble.

Western Bootie and Printed Dress

These ankle boots have subtle Western details, making them incredibly versatile. For the sake of an easy outfit equation, pair them with any manner of flowing printed dress in a fabric appropriate for fall or winter, and keep accessories minimal and chic. It's a pulled-together approach in 60 seconds flat.

Chunky Platforms and Relaxed Silhouette

The most substantial boots silhouette can sometimes look especially exaggerated when paired with skin-tight clothing. If that's not what you're going for, we suggest an all-around relaxed fit—such as with an oversized shacket and non-skinny jeans—to create a balanced look for your chunkiest platforms.

Kitten Heels and Knit Maxi Dress

Conversely, try pairing the slender silhouette of kitten heel ankle boots with a skimming, maxi-length knit dress. Add elements of intrigue with chunky jewelry and a shoulder bag with sleek hardware detailing.

Lug-Sole Boots and Cargo Pants

For the utilitarians among us, this combination of cargo pants and lug soles may be just the ankle boot outfit you’re looking for. The addition of a cheerful striped sweater and colorful crossbody bag adds some playfulness to the practicality.

Snakeskin Booties and Elevated Neutrals

If your ideal professional uniform includes a mix of dreamy neutral tones, take a stab at this palette of black, ivory, and saddle brown. For an unexpected addition, pair with snakeskin boots. The block-heel design is a versatile silhouette, too, so these can be styled with plenty of other combinations going forward.

Combat Boots and Modern Matching

Chic taupe leather serves as a perfect contrast to these combat boots’ heavy soles. The style works with dresses or other designs that have movement, but it also looks great paired with a denim matching set. Style with a thin, printed turtleneck to break up the solid colors a bit.

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