Yech. I liked what I heard off the first couple albums & thought she looked attractive in the videos for those singles.
Then came that one where she’s in the zoo or whatever, wearing that godawful red lipstick & really heavy eyeshadow. “If it Makes You Happy”, I think, was the song.
I think she’s gone downhill from there…Her face has become drawn (perhaps due to a healthier lifestyle, as at least one other Doper has suggested) & her hair, makeup & clothing have whored up in an attempt to compete with the young’ns.
The competition isn’t so much in the Christina/Britney dept., I don’t think; that’s not her genre. It’s more in the “cute young singer/songwriter/musician” dept. - Alicia Keys, Vanessa Carlton, Michelle Branch, et al.
Or maybe she just likes how she looks. It takes, as they say, all kinds.