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My freshman year of college I bought a pair of tall Frye riding boots that quickly became the star of my fall and winter wardrobe for the next six years. I wore them so often that I had to have them resoled twice. But when I pulled them out of the back of my closet recently during a major wardrobe overhaul, I found myself wondering if I could still pull off my once beloved knee-high boots without looking dated. So, to Pinterest I headed to find all the knee-high boot outfits a gal could dream of that are also fresh, modern and 2023-level chic. Below, ten gorgeous ensembles that are easy and fashion forward, all featuring our favorite knee-high style—plus two combos that are, unfortunately, too dated to be cool in 2023.
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