Barefoot in the Park?

I attempted to jog a couple weeks back when we had ridiculously nice 70 degree weather in February. It was a worthy attempt, roughly an hour of jogging/walking/trying to keep my iPod earbuds from falling. The day however, I had some major ankle pains, and not in the good "man I really worked my ankle muscles" way..

Now I've never been a fan of tennis shoes. Nothing says "I'm a tool" like wearing tennis shoes everywhere. But I love me some bare feet. I was always the crazy hill child running around without shoes as a kid. So when I discovered the so-called phenomenom "Barefoot Running," I thought I should give it a try ... when I have money to throw down on some hip "five fingers" shoes.