Find thrift stores near a college. College kids cycle through clothing like crazy - especially at "fancier" colleges. I just moved near Purdue University, which is a Big 10 school, and the thrift stores here are AWESOME. I went from no female clothing to having a feminine wardrobe 4 times the size of my male wardrobe, and all of it super cute, for $150. Sadly it's become a bit of an addiction.

So far I'm in for about $700, which includes wardrobe, Tria for at home facial hair removal, doctors appointments, bloodwork, and a 6 month supply of estrogen/spiro.
Sadly I'm at that age where testosterone has left my face pretty well fugly, and I'm probably never going to be able to afford FFS. So, yay for a lifetime of body dysmorphia.

But, I'll still find happiness as I get more and more closer to being the "me" I was supposed to be.