There are a lot of reasons why a woman would point out she's pretty...society tells us that we can't be smart and pretty, funny and pretty, outspoken and pretty, and so on. It presents beauty as a choice, something we have to sacrifice if we want strong personal qualities. Personally, I think it's great if a woman thinks she's pretty and still isn't afraid of her personality!
As for makeup, I see what TeaEarlGreyHot is saying. I understand her point of view. I get certain messages when a woman wears makeup, too; they're just different messages. I tend to think that women in makeup look professional. Sometimes I think that a woman is way overdone, or see a girl who is so pretty without makeup (like my friend Holly) that it's a shame she wears it. Mostly, though, I get a positive vibe from makeup; this may be because my mother only wears makeup to work, so I associate it with professional success.