The first time i went shopping for women's clothing other than underwear, was at a Wal-Mart, where I purchased some underwear, leggings, a female sweater, some women's jeans and a scarf. It was kind of frightening because of other people, thrilling, and felt right when I overcame those feelings and I purchased and wore the right clothes. It was not a well-reasoned and well-planned decision to do it, I just felt impelled to do it and could not continue just dreaming about wearing the right clothing. I wouldn't start with Wal-Mart because the clientele that can be very judgmental and lack the manners to not say what they are thinking about other people aloud. As far as Wal-Mart employees go, they are poorly paid, nowhere to be found because the stores are severely understaffed, semi-conscious, often lacking any intelligence, and those with intelligence hate their job and just want to make it through the day (I worked there once, so I have first hand-experience). My second time shopping, I was still kind of nervous, but I went to the mall, and was treated just fine by most stores and was treated really well at H&M after I told a woman who worked there I was transgender. I also wore some of the right clothing in public for the first time. I was a little nervous, but it felt really good to dress how I felt, even if I had some LGBT-phobic comments directed at me by others. I am finding out that I don't hate shopping anymore, even though it would be nice to have nice new clothes magically appear without having to spend lots of time and money.
