Help! Need a restyle for fine hair

[PermanentPonytail]

NC as I'm attaching some pictures.
I know it's been done to death, but I feel like I need advice of someone who might have similar hair/face combo!
I have a square face, fine hair and for the past year I've been wearing it up in a braid or ponytail.
I feel like I need a change, so was thinking about getting it cut quite short (think Ginnifer Goodwin/Michelle Williams style).
I had short hair 10+ years ago, I remember loving it until the point of everyone telling me how I looked like a boy/I would look better with long hair, so I decided to grow it out.
I was an impressionable teenager back then, but can't shake it that maybe it didn't look nearly as good as I remember.
Unfortunately I don't have any photos from that time either.
With young DD I don't really wear it down anymore, and it feels a bit pointless to put it up all the time if it looks the same as a short haircut.

I had a hair appointment last month, was going to go for a chop but chickened out last moment and only got some layers cut in.
My hairdresser thinks I would suit short hair, DH is quite excited about the idea. I know hair grows, but I can't face hating it for a year until it grows back!

I guess I'm just looking for some opinions if it would suit my face, and not look a bit plain paired with glasses. I'm also no expert in hair styling, so I'm worried I'd end up looking even worse than now.
Perhaps there is something else I could do with my hair to actually have some style?

Attaching some pictures of my hair pulled back and worn down.

Go short! Mines super fine, but with my short pixie (very short!!) I'm able to get so much volume and texture into it it looks thick and stylish. You've got a lovely face shape, you'd totally carry it off. Do it!!!!

Thanks frenchonion. I'm just terrified I won't like it and I remember growing out phase was horrific! I'm wondering if I should have just kept my hair all one length as it looked thicker, and learn to make some different updos instead . Here's what it looked like before getting the layers cut in, which I don't think was too bad!

I think a Michelle Williams style cut would look great on you.

You have large, wide spaced eyes and great cheekbones, I think the cut she had with sideways swoopy fringe sort of thing would work particularly well.

My hair and colouring is similar to yours. I did it in stages. Had a Bob first, then asymmetric style, and got gradually shorter. I liked it and was glad I did it, but have now grown it back out to shoulder length. I think that if you are curious you should do it - it's just hair and if you hate it, it will grow back. But I believe curiosity should be satisfied.