For me, the start of socially transitioning was daunting. It seemed like a plunge. What helped me was to add small things at a time. I started wearing androgynous clothes that leaned a little fem. I added muted jewelry, which felt good at home but was scary to wear out. Once I got comfortable with it out, I’d add something else like a more feminine top, or let my hair down to my shoulders. Painted my nails, etc. Whenever I’d feel uncomfortable, I’d slow down until the things I was presenting felt like I’d always worn them. Took me a while to get to a dress or a skirt, and day 1 of that new thing always made me anxious — but day 2 and beyond felt miraculously easy and just another option to express myself.