Oh, I can SO empathize!! I think these feelings are worse with short hair...and even when you are used to wearing your hair short and love it so, somehow a "bad" haircut can be so demoralizing and somewhat defeminizing. (Often it is not really a bad haircut at all, but just our momentary perception of the cut.) But we are so vulnerable in those moments.
Because I have been through this so often after hair cuts and colour, I try to tell myself to ignore all feelings about the latest hair cut (either elation or despair) for at least three days. It is sort of like finishing a piece of writing, you know? For the first few days, I am in no position to judge. Also, it takes my hair a day or two to "settle" into a cut. I am often really annoyed with it at first and then, voila, on day 3 or 4, I really begin to like it.
I hope that will happen for you. I like the red tones for a change, and you suit the short length! As for your outfit, it is totally, totally fab - a great casual urban fall look! LOVE that mustard jacket on you, love the booties (yay, Siebel bootie twin!!!) and I like the cozy knits, too. I also love the way the bag and gloves pick up your hair. All in you, you look just wonderful.
You have tremendous style.