How to Wear Ankle Boots Now: Your Complete Guide

Ah, the ankle boot, that perennially stylish wardrobe staple that you return to time and again whenever the temperature outside starts to drop. As much as we love our timeless ankle-hugging friends, it can be challenging to come up with fresh ways to style them. There are only so many times you can wear the same skinnies-and–ankle boots combo, right?

To that end, we’ve scoured the street style world far and wide to dredge up some ladies who gave the footwear staple new and exciting spins. Whether they're mastering the art of layering pretty dresses over jeans or bringing their casual outfits to truly stylish new heights, fashion girls are teaching us valuable lessons in how to wear the ankle boots we know and love. Take note, readers! These cool outfits bring the best of this season's ankle boots. Copying them all is highly encouraged. Keep reading to discover 16 fresh ways to wear ankle boots right now, and shop the coolest pairs!

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Style Du Monde

Take note! This is how a dress over jeans is done.

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Style Du Monde

Cropped flare jeans are essentially a showcase for your cute ankle boots.

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Collage Vintage

Finish off the look with an of-the-moment baker boy hat.

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Style Du Monde

White boots and kitten heels are two of our favorite shoe trends right now. Combined, they pop against a dark outfit.

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Style Du Monde

Ground flirty florals with leather boots and a boxy blazer.

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Collage Vintage

A bright red patent leather brings your jeans-and-a-tee outfit to new heights.

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Collage Vintage

Try an asymmetric hemline with the classic boots.

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Style Du Monde

White boots turn even the most classic outfit into a chic statement.

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Collage Vintage

Kitten heels are a touch more elevated than flat boots and strike the perfect balance with a dress.

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Collage Vintage

This combo is giving us collegiate vibes in the best way possible.

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Collage Vintage

Throw on a stylish checkered coat.

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Style Du Monde

Convinced you need a pair of white boots yet?

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Collage Vintage

Combat boots and leather accessories ground a pretty floral frock.

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Collage Vintage

Wear a block-heel pair with a colorful dress.

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Style Du Monde

Leather pants and a graphic tee make up the ideal off-duty outfit to wear with booties.

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Style Du Monde

A pair of black ankle boots will never fail you.

Keep clicking for some stylish ankle boots to shop now:

We never thought we'd say it, but we're into cowboy-inspired boots right now.

Available in sizes 36 to 41.

If you purchase a pair of red boots, let it be this pair.

Available in sizes 36 to 40.

We love a good contrast heel.

Available in sizes 6 to 9.5.

This pair will take you to all your holiday parties.

Available in sizes 5.5 to 12.

Mark our words: Lavender will be everywhere come spring.

Available in sizes 36.5 to 39.

A satin finish adds a luxurious element to any outfit.

Available in sizes 36.5 to 39.5.

These are almost too pretty to wear. Almost.

Available in sizes 36 to 37.

A brown leather will last you for years to come.

Available in sizes 6.5 to 9.5.

We always say yes to velvet.

Available in sizes IT35 to IT41.

These statement-making boots will bring every look to the next level.

Available in sizes 4.5 to 11.5.