It took some courage for me before I wore a dress in public. I then realized it was better than wearing pants.
With pants, there is still some room for gender ambiguity because men wear pants. With a dress/skirt, you scream "female" unless you're wearing a Scottish kilt.
My mom also said that the pants don't look so good on me, and she's right I think. She said that the dresses look far better on me. Could be hips or other stuff. But now I am shifting rapidly to wearing mostly skirts and dresses.
Not for nothing, don't expect perfection. People will stare, people may laugh, people will do things. Especially if like you and me you're relatively early on. I'm only 6 months HRT. Don't worry about them. Be yourself and be confident. Once you learn to tune them out it is very liberating.
For me, wearing pants was a crutch. And it was very silly using it as a crutch, because I want to be perceived as a woman, right? So why was I dressing in a manner that had people doubting that I was one? I basically wore pants because I could "fall back" to looking like a man when I needed it. But what I was doing was pretty dumb in my opinion. When you free yourself then you can be yourself.
