Inside: I'm gonna go against the grain and say the shorter hair looks by far more feminine to me. The husband agrees with your choice of longer hair. You look like of women in their 30s and 40s I know with your hair pulled back in the faux-short style. I wouldn't cut it, personally. The only short style I could see working for you would be a buzz cut, but I don't think that would look right on you. You look pretty spot on to me as an andro guy in the bottom right photo in casual wear. The layering to me helps. I think colors like blues and greens work pretty good for you in general from what I have seen in your posts. Also, I think the slightly darker hair could help. Maybe a shade or two darker brown? Black, given your complexion would wash you out. That might help you get the reading you want.
Edit: I remembered who it was you remind me of! Judd Nelson, the badass from the Breakfast Club. I'd inbed a picture, but I am feeling overly lazy and I can't remember my password to photobucket. But, that is who you remind me of pretty damn closely. Especially with your hair like it is.