To be honest, the bottom two are the most workable in my book. The blouses in the top three is a bit too much, especially if going out for the first time. The jacket in the bottom right may be a tad to "feminine", though in my eyes it looks great, I would lose the forms entirely, you are going for a man in skirt look, or an androgynous look. Men do not have shapely breastsAt most men have moobs, and they are not viewed at in a positive manner. I am just looking at this when it comes to your comfort level.
Comfort is really the key. Take my forays of late. Last weak I did not wear pants the entire week. Every day I wore some type of legging. At first it was in an athletic look, and flat black leggings, and low boots. The next day I donned my disco pant, rocker shirt, tall combat boots, and loose shirt. The next day I was more daring. I wore my dark blue leggings, with my combat boots, gray t shit, with a dragon motif. Thursday, The shiniest pair of black leggings I have, low ankle boots, nice dress shirt with a belt, so it formed a tunic. Then Friday I wore a more athletic style, with my white sided leggings, tennis shoes, and t-shirt
All of these either drew no comment or some kind of compliment. But as I said a key fact was my own comfort level. I do not quite have the courage to wear a skirted outfit quite yet, but I do not count the possibility out.
Your looks are descent, and if this world were not sexist, they would be fully acceptable. I am very partial to the lower left the more I think about it.