I often go to work dressed in women’s clothing, but with an androgynous enough look. Panties, women’s jeans, a women’s tee shirt, women’s flat shoes, women’s low rise socks. When I use the gym at work (even though all visible skin has been waxed) I am in women’s shorts and an androgynous tee. My sneakers, while men’s, are generic enough at a pure black canvas Converse Chuck Taylor All Stars. And if the weather isn’t too cold or too warm, I may have a women’s cardigan or women’s jean jacket.
If someone looked closely, they might see that the clothing are women’s. Sometimes the top will have a deeper V neck than you might find on menswear. Or the material is not typical for men’s. Or there is a small slit at the waistline, perhaps with the back being slightly longer than the front. I have one black top that if you looked very closely, you would see darts where my breast would be. Some of my tops are designed for a women’s shorter torso and may be a bit short on the waist. The jeans have smaller front pockets that I can fit my phones in (one work, one personal) but I can’t fit my wallet in. The jacket/cardigan has the buttons on the women’s side.
Then there were a couple of times I went in much more obvious women’s clothing. Once, my daughter had her senior trip. I had to bring her to the school early (like 4 AM). After getting home, I came to work wearing a skirt and slipped into my office (I took the back route rather than through the lobby where I knew there would be more cameras) for about 90 minutes while watching some mandatory videos before changing when I knew people would start coming in.
One Saturday evening I was home dressed (but no makeup or wig) when a problem came in with the production systems. When I couldn’t find the problem with the support people over the phone, and not having the work computer at home, I tucked my stuff into my men’s clothes and went in. While things were booting, I changed out of my clothes into the women’s clothing beneath. I quickly got the problem fixed. When I left, I left wearing the skirt and top I had on. I know that there are security cameras, and even though the parking lot was empty, there are other parking areas in the complex so the possibility of being seen was not zero, but everything went fine.
Twice during the pandemic, I came in on a Saturday fully dressed, wig, (daytime) makeup, to pick up things I needed from my office. Again I wasn’t spotted.
Twice (and once this week!) I was about to change into my (women’s) gym shorts until I took it out and realized I had grabbed a skort instead! They come from the same company, one is an identical color to my shorts, and are made of similar materials. When folded, it’s hard to see the difference, but when worn it is obvious. Needless to say, I stayed in my jeans for my exercise that day.