Gotta concur with the Goodwill recommendations; a great place to figure out the basics (sizes, what styles suit you, and there's some really good deals on jeans there). Goodwill mistakes are $5, not $50.
Makeup? This is something I do tend to spend a little more on. My little makeup bag as a mishmash of Maybelline, Rimmel, Revlon, that kind of thing - the major Walmart level brands, nothing fancy. The cheap cheap stuff (and I've used some dirt cheap stuff before) didn't seem to cover the masculine bits and pieces very well - remnants of beard shadow tended to show through, eyeshadow was not good, etc. I went the dollar store route at first, but it really made me look far worse than I needed to, perhaps because the choices are so limited and it was a case of having to pick between a couple of dollar store choices instead of the fifty you can find at CVS. Maybe I've got lots of ugly to hide. But there's lots of good brands out there, and I'm dying to try ELF now thanks to this discussion. Try a range of things, see what works for you. It's not too expensive if you can keep your makeup addiction under control.
