Can I rock this?

I think I might be at my breaking point. I've been growing my hair out for 2 years, and I might be there.
You know? When you are having bad hair day upon bad hair day. Where you are fed up with the additional conditioning, brushing, and styling... only to look only half messy.

I'm trying to decide. I once had my hair this short, and felt a little masculine. With long hair, I can at least put it up in a granny bun to keep it all out of my face. I can wear hats.

But, on the flip side again, my hair is really fine. It looks rattier than it really is, it's prone to static, and I spend WAY too much money on volumizing products.

People, I need help. What do I do? For reference (and for those who haven't seen me lately), here's a recent pic.

And here is an in-between option....

I'm putting it to a vote.