You've got a good head of hair that a decent barber should be able to cut to get it under control. If you want to get an approximate idea of what you'd look like sly, go to a barber and asked to be buzzed down with no guard (some barbers won't do this, others will). You'll get an idea of how you will look. If you like it, go home, lather up and shave. If you don't like it, your hair will grow back pretty quickly.
As to head shape, don't worry about it. No one has a perfect head, so shape doesn't matter.