I've had really really short hair a few times and I love it, but I got bored with it which is probably why I used to get it dyed different colours also

The one thing I would say is not just to get it cut short but to get it styled. Big difference IMO. If it's styled properly you can let it dry naturally and use minimal product to keep it in place.
I had a shocker once that looked like a cheap barber had thought I was a 12yo boy. It was awful I think it was worse because I'd had the best ever haircut 6 weeks before but went in for a trim to find out my regular stylist had gone on holidays.