I started about the same time I started HRT. I think at first it was a bunch of panties, so I could at least have something feminine on without it being noticeable. Then I think I got cute jammie pants to wear around the house. Maybe two months in I started going shopping with my mom since I was still uncomfortable in the women's section alone, and I got some jeans. Got a small simple purse with skulls on it around that time and started carrying it with me regularly. Three months in I sometimes went out a bit mixed, like women's jeans and a guy shirt plus my purse. Didn't want to draw too much attention to myself. But this was the point of male-fail as I was getting ma'am'd and wasn't really trying to pass. Once I reached that point, I got more female clothes. Some rather blatantly female stuff. Got my eyebrows done and I was passable except for my voice. Got some high-heels and stuff like that too. I tried taking it slow but it all happened pretty quick. So about three months in I had enough clothes for a week. And then I ordered or bought quite a lot more clothes, especially because I was going on a trip. 4.5 months in, I went full-time and had enough clothes for a week and a half to two weeks, and over time I've just added from there.