I remember the "Lucky" video (it's actually one of my favorite songs by Britney.)
I guess that was as close to Old-Hollywood glamour as she'll get - but it still looked cheap to me (badly sequined gowns and feather boas.)
Her "people" were the ones keeping her looking tartish and tacky - I get it, she's a popstar, and they branded her VERY well.
Regardless of how she looks or her current situation, I love the new album unapologetically.
http://preppylife.tumblr.com/