I have always thought about going really short. Maybe even really short and a little spiky (although I have my doubts if hair gel would work on my notoriously unstylable hair).
Of course, my face looks nothing like Hepburn's or Ryder's. And my current stylist gasps in horror whenever I mention going super-short. Now, I overall trust her judgment, because the long, layered cuts she's given me have been fantastic. My hair has body and movement now. It looks good.
Short cuts are more expensive to keep up, but easier to care for. Money is snug, although I could probably pay for it out of my allowance.
I tend towards thinking, "Try it! It'll grow back if you hate it!" As they say, you'll regret what you didn't do. And if it's awful, the Spud is too young to be embarrassed by his mom's ugly hair.
Do I try to convince my current stylist to cut it or (gasp) go elsewhere?