Almost every pair of pants is at least a little bit cropped now, whether a Sabrina-style ankle-revealing crop or the wide-leg crop popularized by Jesse Kamm and Everlane. This presents a challenge: What shoes can you wear with them in cold weather that are nicer than a sneaker and socks? An ankle boot or a heel leaves a bit too much lower shin exposed to the frigid air. The key, then, is a bootie with at least a six-inch shaft, so there’s not a huge gap between the hem of the pants and the top of the boot. The shaft should also be somewhat tight up your leg. And voilà! The perfect way to wear your cropped pants into the cold winter months.
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