16 Outfits to Wear With Your Black Ankle Boots

We know, we know. There’s a whole world of shoe trends available to try right now. There are Western cowboy boots, over-the-knee silhouettes, bright colors, and white pairs that channel ’60s mod, but nothing is as valuable to your wardrobe as an old faithful that never steers you wrong. For us, that’s black ankle boots. Predictable? Sure. Wrong? Absolutely not.

The reason black ankle boots are (almost) never a bad choice is that they have versatility. They’re not the statement piece of the outfit; they’re the best supporting star—the reason any look can come together effortlessly. To drive the point home, allow us to present you with 16 examples of what we mean.

The below is just a sampling of fall outfit ideas that feature black ankle boots. They’re cool, uncomplicated, and ready for copying as soon as possible.

Style Tip: Anna Wintour wears her black ankle boots with jewel tones and animal print. Think about that.

Style Tip: No need to choose between slim-leg jeans or a more relaxed fit. Block-heel booties work all the same.



Style Tip: Welcome sheer tights back into your wardrobe this season.

Erin Fitzpatrick, Fashion Editor at Who What Wear, Is Photographed Attending Stockholm Fashion Week


The Style Stalker

Style Tip: Update your straight-leg jeans with a fun, colorful coat and graphic sweater like our senior news editor, Erin Fitzpatrick, does in this photo. 

Style Tip: Love neon? Your black ankle boots will complement, not compete.

Style Tip: The same can be said for voluminous dress silhouettes.


The Style Stalker

Style Tip: A chunky lug sole will add a little edge to a bright and playful dress.

Style Tip: A midi skirt is the perfect way to show off your ankle boots.

Style Tip: Combat booties balance a feminine and romantic maxi skirt.

Style Tip: Simple black ankle boots will pull even the most casual of ensembles together.



Style Tip: For an of-the-moment look, style rubber lug-sole boots with a cute pair of socks.



Style Tip: Loose, gray jeans will feel ultra-cool with black Western-style boots.

Style Tip: Fall dresses feel decidedly cooler with super-chunky lug-sole ankle boots.



Style Tip: One of the top boot trends of this season is lace-up boots, and we can’t get over them.



Style Tip: Lace-up booties and midi skirts are one of our favorite current combinations.

Shop Our Favorite Black Ankle Boots

This post was originally published at an earlier date and has been updated.

Next, Ballet Flats Are Back, and These 16 Outfit Formulas Make Them Look Chic