Yeah go for it. Won't know until you've tried it...have a go, if its really bad it'll always grow back soon enough anyway.
I think short hair could really suit you- you've very good bone structure, but I really don't think you should get the 'scene' haircut. They look a bit common. Try a 1940s style cut? That would suit your pretty and natural face.
Perhaps get your hair cut into short layers maybe? But keep the length I'd say. It is fun to have a change now and again though.
Your picture doesn't work for me. I don't think that style would make you look older though tbh, to me that looks more like a 15 year olds style.