I guess Anna Wintour has stuck with that bob in hopes of crafting a timeless, Diana Vreeland-like iconic look, but it has always looked more to me as if she just loves the wigs. Which seems to go along with her overall look of clothing wearing her instead of the other way around- she takes risks, but she tends to look more nuts/over accessorized than she does glamorous and creative. It's like everyone's afraid to criticize her, but is she really ever going to be cited as a style icon? I don't think so.
Maybe she should have gone with a nice Zum Zum-esque prom dress like her daughter.
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