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These boots have a sleek equestrian vibe that pairs effortlessly with riding pants, sure, but also with almost anything else (case in point: the patch-pocket mini on our model here). And as you’d expect from a good pair of riding boots, they’re really comfortable (whether or not you actually plan to wear them to the arena). The buttery calf-leather upper and insole soften like a second skin to the contours of your instep, and the crepe sole has a lightweight feel that belies that big boot energy.