I'd say the second one mate - maybe throw a couple of highlights in for good measure. To be honest, I'm at a similar juncture with my hair - it's quite long at the moment. I'm either going to straighten it into a bit of an emo fringe or have it short and spiky and dye it black.

Either way, the moral of the story is to go with what you feel comfortable with, whilst trying to make it stand out a bit.