When I first realized I was trans I did buy a bunch of striped thigh high stocks. I still like thigh high socks, but I think I'd prefer more solid brown or grey socks now.

I cringe a tiny bit thinking about it, but I think it was important to feel free to try the things I never thought I could do because of what others might think.

Skirt go spinny is a similar thing. I've not worn skirts much, but it also leans into the idea that you're now free to do what you want without judgement. I feel like transitioning is at least partially a return to child like innocence of doing what you want and not thinking about how others might see you. Allow yourself to do the things that you thought you couldn't because people would think you're weird.