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When you think of knee-high boots, images of denim jackets, the West, and full-on Americana probably come to mind. That's because this style is a classic. A staple. And, now that fall is upon us, there's no better time to invest in a quality pair of riders. Tuck your skinnies into a flat iteration and pair with a chunky sweater for the weekend, or opt for a heeled pick with a full, wool skirt and blazer for the office. However you hope to wear your set, you're sure to find a pair ahead, including velvety, studded versions and shearling-trimmed buys, that you'll be able to wear today and 10 years from now.