25 Ways to Wear Your Over-the-Knee Boots All Winter

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In the world of cold-weather boots, over-the-knees are probably our favorite. It’s hard not to obsess over footwear that actually let’s you rock a short skirt in the dead of winter — but on the flip side, tall boots are notoriously hard to wear. One false pairing and you can venture into lady of the night territory. Though we love Julia Roberts, we’d like our look to be a little more Gigi Hadid and a little less “Pretty Woman,” thank you very much.

MORE: The 20 Best Pairs of Over-the-Knee Boots at Every Price Point

Whether you’re planning on busting out a dusty pair from the back of your closet,or ponying up to purchase a new set, we’ve nailed down 25 ways to wear thigh-high boots during the coldest months of the year and still look totally chic (as opposed to looking like you’re out trolling for a date).

Originally published December 2015. Updated November 2017.

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25 Ways to Wear Your Over-the-Knee Boots

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Photo: Yvonna Groom/StyleCaster

Photo: Getty Images

Photo: Getty Images

Photo: Getty Images

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