My first times out (in the fall of 2015 can you believe it?) were wearing women's super skinny jeans under a loose male T shirt, going to fast food. First a drive through, then a sit down. Nothing bad happened. I quickly went to wearing women's skinny and super skinny jeans all the time, and carrying a Coach man bag, and no one noticed.
I went to the mall shopping all the time with my wife, me wearing women's skinny jeans under a t shirt or sweat shirt, and no one noticed. I always wore women's sneakers or slip ons also.
My first time in full dress head to foot was going to my first therapy appointment, and then after that, I always went to weekly support group in full dress. Skinny jeans and cute blouses at first. Sandals with nail polish on my toes, and carrying a female purse. I am starting to add dresses and skirts in the mix now that my hair is growing out and I am mostly through facial hair removal.
My support group goes out to dinner each week after the meeting, and we go to restaurants where the management is known to be friendly and tolerant. The workers who know us there always greet us with a smile, and they ask if we skip their place for a week and go to a different one.
My first few dinners out I was a bit nervous, but I got better and better at navigating the world in full dress without being self conscious.
Recently, after coming out to my dentist, I had to drive to another office half an hour away for a root canal. I made the drive and the office visit in skinny jeans and a tight little women's scoop neck T shirt over a lightly padded bra with "the girls" clearly visible. Nothing happened other than an older man in the waiting room kept sneaking looks at me. I don't know whether he thought I was hot or didn't know how to gender me.
In the early days I carried a "punk out shirt," an oversize men's t shirt to hide in if anything happened -- but nothing ever did. Now I don't bother. But I do carry a men's long sleeve t shirt and work gloves in case I need to change a tire. And if I wear heels, i carry a pair of slip on flats or womens sneakers just in case. But after all, just about every girl does that.