Frankly, it feels like a bigger deal than it really ends up being. Just go for it. I'm buying short shorts this summer and I don't give a fuck.
I will say that sometimes it's a good idea to wear pants and look normal, though. Job interviews, meeting someone's parents, trying to get a good deal on a big-ticket purchase, etc. I also wear pants at the gym because I'm there to work out and kind of just want to do my thing as invisibly as possible. But aside from that I wear skirts all the time, so my legs are almost always fully visible. Nothing bad has ever happened. Even at the pool, I get more approving "Damn gurl, u got courage, rock on" looks than anything.
I recommend it.