I'm Genderfluid and would like my appearance to be a bit more flexible.
My hair is currently long - just past my shoulderblades - and I tend to just wear it tied back all the time and not think about it too much. It's this way because it's nearly always been this way. I did go short for a little bit while in university and had various results:
me aged about 19:

19/20:

20/21:

and then I let it grow out again.
I think I got to the point where I was putting on a bit of weight and felt that shorter hair just made my face look rounder (though to be honest getting the fringe probably didn't help there).
right now I look like:

so I'm not carrying as much weight facially, but I still don't have the thin face I had at 19.
I guess my real fear is that if I get my hair cut short again, it will look terrible and then I'll spend the next 6 years or so trying to grow it out.
this is the sort of thing I'm thinking about:


though my hair naturally parts just off center on the right side of my face, so maybe this wouldn't work.
so... help please?
Suggestions of hairstyles which would suit my face better would be good.
Or how to go about finding a helpful hair stylist.
Or just tell me it's only hair and I can always wear a hat if it turns out awful.
right now that whole thing just makes me want to freak out. I want this. but I'm scared.