I know what you mean Merry. I think there is a certain stigma associated with caring about your appearance, especially here in by-the-bootstraps America. Some people wear sloppy clothes, messy hair, and the bags under their eyes as some kind of self-righteous badge of honor ("I don't have time to worry about how I look! I am much too giving, hardworking, and sacrificing to deal with such trivial and shallow matters!"). People who do pay attention to their appearance are often judged as shallow, vain, selfish, arrogant, etc. I remember a few moms here talking about how the other moms at daycare/preschool/wherever would make some negative remarks regarding their put togetherness. I chalked it up to jealousy. But this attitude does seem to give a lot of moms and other women a complex.
Speaking from the perspective of a daughter, I would love my mother to spend more money on herself and feel comfortable and confident. I wish she could have been more of a style role model for me. Unfortunately she is just like those WNTW people. She doesn't think she deserves it and she is so unhappy with her body and her appearance that she doesn't even think the effort would be worth it. I can't help but believe some of that has rubbed on me. She is a busty apple and hates her body, so what am I supposed to make of my own? For this reason, I think self-maintenance is not actually just about you.
As for Ms. Boyle, I agree she'll get some backlash if she gets a makeover. If it's just some new clothes, a bit of makeup, eyebrow grooming, and a haircut, I think that's great. That is just enhancing who she is, not changing her. If it gets to the point of plastic surgery or dramatic weight loss (beyond just getting in shape), then I think a backlash might be justified. I don't know though. If she now has the means to do whatever she can to make her feel better about herself, I don't see anything wrong with that. She still seems like a positive, confident woman, which is VERY admirable considering where she came from.
Seems to me like women get ridiculed when they try to look good and when they don't try to look good. The only way we can win is to be natural perfect beauties. Screw that! I want her to just do whatever makes her happy.