I'm posting here with still pretty short hair. I usually just get it faded up to very short (aka, the marine cut) because it looks nice and is easily maintanable, but I think I can look good if I grow it to a medium length again. Then I don't get asked if I am going into the service.
Do people like the idea of a mussy spiked look? I have a cowlick on both the left and right front, and the left and right back of my head, so sometimes gel doesn't work that well and my hair just flips to the side.
Also, Andy and May, I think maybe you should try going with 2 or 3 cuts, start with say shoulder length, and if you want it shorter, cut it again, and if shorter still, cut it YET AGAIN. It takes a lot less time to make hair shorter than it does to make it longer, so if you cut it too short, you may regret it.