So up until a couple of months ago, my dyed dark brown hair was about armpit length. Until I had the urge to chop about 3" off it.
I really like it & get on with it being shorter. I have a really really round face shape & full chubby cheeks. It's not like when you google hairstyles to suit a round face shape & photos of Cameron Diaz, Kate Winslet or Kirsten Dunst come up, they don't have a round face compared to mine!!
Anyway, I'm thinking of going a little bit shorter. I have a short neck. Also I'm thinking of a subtle ombre as well, I quite like this but not sure if it would suit me. Perhaps not as short as this but just on the shoulders. I'm 42 & just want a change I suppose or something a little bit edgier than what I have now. My natural colour is like an auburn colour but I colour it dark brown.
I'm similar to your description. I would say not to go shorter -I think longer hair lengthens the face and neck. How about just going with colour change and experiment with clipping up,curks to go out etc?