My wife [and I] would prefer that people who know me remain ignorant about my clothing choices.
I would like to wear whatever I want to more often.
One guy at work is one of those whom I would prefer that he stay forever ignorant of my fashion choices. (He was the hardware guy that came up and offered to help me find something the day I went into work in the shorts and hose.)
So, wearing clothing is not daring. People have worn skirts in my office before. (They were women.) So that's not daring. I do not recall ever seeing one of them wear sheer hosiery, but it still isn't daring. Since I don't want them to know, it is dumb. So, it feels like nothing I did was daring, except trying to be exposed while remaining invisible.
Other daringly dumb things that I have done at work.
I did not blog about this. I think this happened on Labor Day (US Holiday). It may have been another day. I was the only person in the office except for the front desk person. I think that I wore my androgynous ladies' flats to work with women's trousers and, I think, dark hose. When it was clear that no one else was in the office, I changed into a skirt and worked at my desk in privacy. I worked like this for a few hours. I decided to go to the break room and make my lunch. I kept on the skirt. I heard a door. The front desk person was on the move. I was not too worried. If she learned that I wear skirts, whatever... But, I wasn't going to facilitate it if I could avoid it. She did not come to the break room. I put what I could of my lunch back into the plastic bag that I had brought it in, and carried the rest and walked back to my desk. I turned a corner and encountered her. I was carrying my bag so that it obstructed the view of the front and center of my skirt. We both smiled and I bashfully said something like, "Excuse me" or "Hey". I forget... She smiled and behaved rather normally. She walked on by me. I proceeded. I glanced back and she never looked back at me as she returned to the lobby. Later, I changed back into my trousers before going home. I said as I left, "You weren't supposed to see me like that." She expressed confusion on her face and said, "Why, because of your shorts? Were you hot?" I said, "Since no one was here, I decided to change into something more comfortable." or something like that. I am pretty sure that I was wearing off-black pantyhose, but she must not have noticed. (whew!)
The other thing: I went to a conference. Another guy from work went too. They paid for us to go. The first day of the conference, I observed that .5-1% of the people there were expressing some sort of LGBTQ or other presentation. There were several people who were either full-on transgender. There were others who were less clear. A couple of people were in Japanese anime style clothing. (Short dress with above-the-knee socks.) I am pretty sure one was born male. Some people were seemingly presenting male, but they were wearing some female garments and makeup. One guy was there with his wife. I met them. He was in a dress and 1.5 inch, chunky heels. He had long hair that was shaved on the sides of his head. No makeup. blah blah blah... I decided to wear a skirt on day 2 of the conference. I called my co-worker and told him that I was going to do it and asked him not to tell other people at work. I did it. It was an amazing experience. I just lived my life for at least 18 hours while dressed pretty. I rode public transit, ate meals, interacted with people... I do not know if my coworker ever told anyone in the office. I has never come up. And, of course, it doesn't matter.
Joey