Remember that day, maybe eight years ago, when you realized you could wear skinny jeans under knee-high boots? It was magical. And suddenly, your favorite outfit probably consisted of an American Apparel hood under a tweed, contrast-piping blazer, dark-wash skinny jeans, and buttery soft, knee-length leather boots that you ended up wearing every single day. Surely, that wasn't just us...

But then, came along the ankle boot, and staged a coup. And knee-highs suddenly fell out of favor…until now. Because these days, it's possible to wear a riding boot without looking like a college kid. In modern heel shapes and inspired, leg-lengthening styles, these are definitely not the boots you imagined wearing on that dream date with Wilmer Valderrama.

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