Okay, I'll wade into these so-far-male waters...
First thing I did was to acquire a friend in the community (a local transwoman). Then I found and started attending a local support group - went to the first meeting in total guy mode.
First thing I got for presentation was a pair of women's jeans and a top from Old Navy. Actually, not quite true - my first purchase was panties. True story: When I was waiting for a fitting room to try on the jeans, the song "You Make Me Feel Like A Natural Woman" by Aretha Franklin was playing on the loudspeakers. I kid you not. The jeans, top and a tube of lipstick were my first complete outfit - I didn't even have a wig.
NOW, of course, I have clothes, 5 wigs, and makeup. And nicer panties. And shoes, and a purse. I will not bother with breastforms or such, I'm not remotely trying to pass at this point, and I'm hoping to get on hormones sometime in the next six months, and let them work their magic, such as it will be...