Could supershort hair work on me?

My hair is pretty short now (see avatar) and most people think I look good with short hair. I have an oval face, high cheekbones, full lips and normal sized straight nose, and big eyes. I'm 5'5 and 140 lbs, but curvy (36D-28-38) with a large frame, and people generally think I'm taller and thinner than I am. My hair is naturall pretty straight and flat, and dyed dark auburn. I'm thinking like Alyssa Milano's old cut or Natalie Portman several months post-V for Vendetta. I don't want my hair to be any longer than it is now, because my hair used to be long and it was hideous and difficult, but I am considering going shorter.