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It's the straightforwardness of the sexual imagery in the Elle photos that trips our cultural inappropriateness alarm. Instead of sexualizing her childlike innocence and naivete, it pictures her as a sexually-motivated and experienced teenager (similar to the apparently outrageous bed sheet photo). Miley has crossed that fine cultural line between sexy purity and sexiness that is actually sexual.
The boots don't bother me. I don't know how affluent teenagers dress in San Francisco, but those boots or variations on a thigh-high boot theme are a fairly common sight across a vast spectrum of fashionable women in New York City, including rich teenagers in my neck of the woods. (Think less "mid-life crisis," more "fashion victim.") I saw a variation on those boots in Delia's, the catalog for teenage girls. My nieces keep me current on what's stylish. What I don't like is the "Come hither" stare combined with the "Fuck me" positioning on the table. Billy Bobby is definitely upping the game in pimping out celebrity offspring.