Yeah, I get it: It's scary out there, and can be quite nerve-racking at first. All kinds of crazy stuff can & does happen -- or it could be entirely uneventful.
It does take a lot of confidence to rip that band-aid off in one fell swoop, so to speak.
But have you ever tried a tiny baby-step to help get you there someday?
One way of doing that is going out completely as a guy -- except for one outwardly-visible thing of your choosing.
For example, earlier today I had to go to the post office & grocery store. And you think I'm gonna let the GG's have total dominion over yoga pants during an errand run? Aw, heck no!
My outfit: Men's running shoes, black bootcut yoga pants (with a thong underneath ), and a charcoal men's t-shirt which, although not "a dress," was long enough to cover up most of my butt & front, as I didn't even "tuck" & the pants do hug the thighs & rear.
The only thing that kinda sucked was having no pant-pockets. Ain't I ain't carrying a purse, at least for that. Luckily, the t-shirt I chose has a front pocket, so I tossed my wallet in there (made it as light as possible first), and just kept my keys in my hand.
And it felt great the whole time out there. Very comfy! I looked in my full-length mirror before I headed out, and it really just looked like a "normal" guy-outfit. I even intentionally kept my ears & eyes out, and nothing out of the ordinary from anyone that I noticed.
Could a keen-eyed GG tell they were women's yoga pants, or at least wondering if they were? Always possible. But really, what's she gonna think -- "Ah, I don't blame him!" ??
Anyway, it's just one little thing to get you used to being all dolled-up out in public. And it really can be something as inconspicuous as what I wore. Do it a few times, and you realize it's no big deal, being perfectly comfortable with it. Then after a while, maybe kick it up a notch, by adding some not-so-obvious women's running shoes, or a women's top that looks more gender-neutral?
Really, you can take it as far as you want. But even just a couple things can get you used to the idea of being out there fully dolled-up in public, to make that "transition" that much easier when you do finally go ahead with it someday.
Give it a try, if you haven't already!