chronic ankle pains

Hi! I’ve been having bouts of extreme pains in my ankles since my early teens.
I am not so sure what really precipitates them – usually running or hiking, but sometimes just a change in the weather or nothing at all, it seems.
I have to miss work sometimes, they last for 2-4 days at a time, anti-inflammatories only cut the edge off the pain and there are no associated swelling or limitation of range of motion per se. And in between attacks, my ankle feels totally fine. As to what caused it, I’ve always ascribed it to repeated eversions and inversions of my ankle in early childhood (went to catholic school, and went playing a little too roughly in those clunky black leather shoes every breaktime).Can you please give me an opinion as to my condition, and what I can do to prevent further attacks?
I am rather active – in the gym for both cardio and weights four times a week, and outdoors hiking or what not on the weekends. I am thinking of getting ankle braces (ASO support), and I would like to make sure they’ll be useful in my case before I purchase them. Thank you.