The first time i actually womaned up was when I was married. My wife helped me into some skinny jeans, and I had a hello kitty graphic tee and all that.
Well that only really lasted a week and partially due to not identifying myself female as of yet.
Other than that, it was about the time I was finding myself out, as to when I started small with a few pairs of skinny jeans, then added more wardrobe, had and still have skirts though I don't wear them much outside.
Currently I double bra to get my shape, and other then that, and I have about 99% of my wardrobe female wear, the one suit I do have that's not female is one that cost nearly $3000 so I can't just toss that out.
The time I did go out in a skirt, well didn't really go too bad, but I disliked the reaction from a few co workers that they had compared me to the Tongan men, that have their cultural wraps and all. So as per that situation, I dont go out in my skirts anymore.
And this all started when I was 28, and if I remember right when I did dress, when I was married, that was I think when I was 26.
Kate <3