I don't mean about the social aspects but just about presentation.
Though i live this full time now (I do not like any label, I just live) but at one point when I was starting out -
The first thing i wanted to learn about was how to do makeup, how to dress stylish, and what sizes do I even wear.
I wasn't on the web at the time nor did i even own a computer yet (around 1998).
I remember asking other TG or drag queens for advice. I also rummaged books. Books didn't help. They showed a bunch of ideas but didn't cover the basics well at all. Don't even get me started about my adventures trying to track down the completely useless book "Miss vera's finishing school for boys who want to be girls". I will just say when I finally got it, I thought it would have the secrets of how to dress like a woman. After reading it, it went in the trash. Worst $15 I ever wasted on a book.
EDIT - there were also a bunch of boring books I read about the lives of other TG. Things like "My husband betty". THOSE really helped.... not.
Drag queens were saying "Use max factor pan stick and cover it with pan cake and then apply powder". What a great idea. Tammy Faye Baker foundation...No thanks.
I talked to a TS lady who I was hoping i could get some help. She meant really well but things she explained were more geared to a TS in serious transition, yet at the time I didn't even know my female shoe size.
So I went to the mall and got a makeover (in the back room so no one would see me). The lady gave me a list of what she used so i could buy it later and duplicate the look. About $200 worth of Elizabeth Arden stuff. At the time I was mostly broke so THAT was not an option. I think I borrowed $50 from my sis to buy (drug store) makeup but i forget what I said the money was for...
With clothing, I realized my only choice to find my sizes was to nervously pick things off the rack at thrift, sneak to the dressing room, see what fit, and note the sizes. Trying to find my bra size was a REAL trip.
Somehow I got all that stuff down pat but was becoming concerned with passing better. I remember hearing things like wearing long sleeves to cover my muscular arms, or wearing 3 pairs of tights to smooth my legs, etc. yeah, THAT is the way to dress... as long as it is not 95 degrees in the dead of summer, THEN what?
As time went on I learned what I was doing but oh my gyod, I would NOT want to go thru the initial learning all over again. Like knowing almost nothing and trying to be secretive about it at the same time.
How did you all finally learn? Was it as much of a mess as I experienced with bad advice/useless books/expensive trial and error?