It was mostly my right ankle that was the issue, but the other one has been sprained as well. First sprain, I had to wear a cast, have crutches, and after that I was stuck in a boot. Then KT tape and braces for months, and lots of PT. I think I've had four or five significant sprains between them, and several less serious ones.
I go barefoot on my property, when hiking, at the park(carefully), and I've gone barefoot around my village(it's not nasty like a city) and even in the village grocery. Though that was after swimming in the creek, me feet weren't dry yet and we had to pick up some stuff.