Dylan - You pass in the first photograph, but not so sure about the second one, probably just the angle. The photo of you with shorter hair does look better, but you're in a very masculine position as well, which does help, whereas we can't see your posture and clothes etc in the first two. At the end of the day it's your hair though, and I could imagine you passing pretty well in real life with your hair either way.
Jared - I'd say that the die earring doesn't help, mostly because I've never seen men wearing dice, but also because second piercings aren't that common in men. I like the other two though, would get some if my holes hadn't closed up from my botched attempt at stretching them...