I've managed to wear ankle length skirts at home for several months around my wife, two teenage step kids and a temporary live-in father-in-law, with no issues except in the beginning when I needed to explain that it was a comfort choice. This has been very nice for me but my wife has been dead set against me going in public in a skirt especially with her, until last night.
Last night I was in the house in a full length black knit A Line skirt, tennis shoes and a sweatshirt with the sleeves cut to elbow length when my wife informed me she wanted to go out for sub sandwiches for dinner. I whined because I didn't want to get dressed to go somewhere. She told me to just put on a long coat and go as I was. SURPRISE!
I took off the tennis shoes and slipped on some black shoes to complement the skirt and left the raunchy sweatshirt to balance the look

This was a special weekend for me indeed. I am becoming convinced by all that I read that it really is me who is holding me back from my freedom of dress and comfort. I still plan to be subtle because I live in a small backward town but I plan to move forward in this direction.
I've also started to mention to people I meet that I am planning to try wearing a kilt for both hiking and otherwise to get their general feelings, and so far (only two women, both whom I don't know) the response has been positive but the underlying message in both cases is "be careful".
I read a post elsewhere that I guy hated to leave home because he would have to change out of his comfortable skirt to go out. I can relate. Many times in the past I have neglected to go do things I needed to, simply because I didn't want to change into pants to go do them. MAYBE that is about to change.