Over-the-knee boots hit hard during the last few seasons, with designers like Chanel, Phillip Lim, and Chloé showcasing their own versions on the runway, prompting retailers from Stuart Weitzman to Zara to follow suit. 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.  

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