maybe im odd, who knows....
years before i started transitioning, i was wearing panties. as time passed, i would buy my clothing from the ladies section in the stores.
basic jeans, tees, etc, became the norm. its prudent to say, i never have been a 'girly girl" and dresses, lace, heels, have never been my style.
My style was more 'country western' if that helps paint a picture.
if i had to give advise on the subject, my opinion would err on the side of caution.
sure, wear female attire, but be conservative. makeup early on the 'less is more' was my rule. dresses and skirts were a no no around family, as was anything overtly feminine and flashy. I stayed with jeans, a blouse, boots or flats over 6 inch sequined heels, and natural color make up used spareingly.
I wasnt out to " shock them into submission".
Personaly, I beleived my family need to be eased into the notion, that I was Lisa, the girl. dressing like I was just " in their face" would have been a diesaster in my family.