Hey guys, I'm in need of some opinions.

I have worn glasses since I was 5 years old... my eyesight is completely horrible, such that my lenses have always been extremely thick, and I've not had much luck with contacts (bad astigmatism, they won't stay properly aligned). The pair I'm currently wearing are about 4 years old, and in pretty poor shape, as well as not matching my prescription any more. So... I'm in the market for a new pair, that hopefully will be a little more stylish than what I'm currently sporting.
Apparently, the dark plastic, squarish, 'geek' look is big these days... but somehow, I think something like that would take me out of the 'nerd-cool' area into the realm of the simply 'nerd'.

So.... what should I be looking for in functional and fashionable eyewear?

Oh, here's a pitcher.
http://img.photobucket.com/albums/v109/naoh37/100_2354.jpg