In my experience, there's this feeling of having to get it right. I was 12 (and in Texas) when I was first allowed to wear makeup and saw it as a "rite of passage." Back home, I am seen as someone who doesn't wear a lot of makeup. I get told I don't wear "enough" or need to put on some lipstick (or get asked if I'm feeling well). Here in Boston, it often feels like you are judged for using makeup and have to explain why you use it (with the disclaimer that you are still a confident person who just happens to like to use makeup).
I think makeup and people's reactions to it often tell more about society's perceptions about beauty (and the underlining pressure for women to "have it all") than it does about the woman who is using it.