Friends, we’ve come a long way in our quest to nail this ankle-boots-styling thing. By now you’ve likely mastered it with jeans and skirts alike. And the natural next step is dresses. Here we go...
How to Wear Ankle Boots with Dresses

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Think Streamlined
By nature, a dress is a statement enough on its own. Be careful not to let the shoe overpower it. If you stick with slim-cut, minimalist ankle booties, you should be good.

Christian Vierig / Getty Images
Think Lengthening
For short dresses, a neutral heeled ankle boot works just as well as a nude pump. (And has way more cool points.) Just make sure your socks underneath don’t show.

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Embrace Pointy Toes For Versatility
Whether you’ve got a mini shift or a flowy maxi, you can’t go wrong with a black, sharp-toed ankle boot on the bottom.

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Use Ankle Boots To Tone Down A Prim Look
Embellished Western boots pair shockingly well with a shirt dress and a top-handle bag.

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Don't Fear Ankle Boots In Warm Weather
Because just look at this spaghetti-strap dress.

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Let Your Prints Flag Fly
Plaid. Floral. Anything works as long as you anchor it with tough ankle boots.
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