You pose questions that are difficult for many of us who call ourselves androgynes to answer. I can only speak for myself, because, like many in the forest, I am an amiable misfit and an unconscious rebel. When I was young, I infuriated those closest to me, first by experimenting with dresses, and later by growing a beard. Cool people in the media for me, would be perhaps Humphrey Bogart, Katherine Hepburn, Errol Flynn, etc. In this forum, I think Kinkly and Pica Pica have cool senses of style. I like shirts with puffy sleeves, tight at the wrists, bright tunics, and knee britches. I like more colors than are allowed in men's clothing stores.
I wear what one store calls comfort mocs, suede slip-ons (in a variety of colors, including red), and hiking boots. I like button-down shirts in pink, purple, pastel green, yellow, and several shades of blue. I also wear some more casual shirts, including some in a misses size 18, but those are not conspicuously feminine. My slacks are in a couple shades of blue, plus I've some khakis and jeans. I always wear a necklace with the Hebrew inscription: I am my beloved's, and my beloved is mine. I carry a tan canvas shoulder purse (Once a woman stopped me to ask how I liked it; she had thought of getting one like it). When I couldn't find just what I wanted, I have sometimes sewed or knitted for myself. My hair is in a ponytail that hangs to the middle of my back, washed and conditioned daily. My beard rates less care.
When my wife asks what she should wear, I usually give her a blank stare. I don't copy anyone's style (though I may adopt elements), nor would I presume to tell others how to live. I am flattered when told I look nice, cooked tasty food, or cleaned the refrigerator with uncommon thoroughness, and saddened when met with disapproval. I am happy when the group of women I work with considers me one of the group, and when I am accepted by the group of women I lunch with and am learning to play mah jong with, and when my wife refers to me as 'she' (or when she tells me she likes my body).
I fear none of this will be of much help to you, but I do wish you the best on your journey through the forest.
S