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Your ankles wouldn't want you to get hurt on your next hike, so you should repay the favor by getting yourself a nice, sturdy pair of hiking boots. A mid-height cuff goes a long way towards stopping you from rolling your ankles or clipping them on overgrown tree branches on the trail. Plus, nothing says, "Yeah, I spend a lot of time outside," like rocking a pair of waterproof boots to your next social function.