I’m out to most people that know me. Work is one of the few exceptions. I’ve written about that before and will skip the details. Suffice to say coming out would be disruptive.
The clothes I wear are more about function and less about the gender they were intended for. That said, I’ve taken things a small step beyond underdressing.
I wear panties daily. They’re more comfortable than guys underwear. I wear no-show sports bras as needed – usually days when I’m using the gym or wearing a tighter fitting top. That’s to support and minimize my small boobs. I wear women’s jeans and a unisex t-shirt most days. On occasion I’ll wear tights under my jeans for warmth and support.
I’m less concerned what my staff thinks and more concerned with keeping them. I’ll continue the guessing game until I can’t do it anymore.