Tyler Bledsoe was probably the first guy I ever realized wore glasses while he skated. I read about it somewhere in an interview with him and while I'd say he has that pretty solid "nerd" look, Tyler absolutely shreds with a wonderful style. Just look at his classic Hallelujah part above. From what I understand, Tyler now is wearing contacts so his face will be frameless for who knows how long. But I don't think I'll ever get past his look with the glasses on.