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There are many delicious things about this 1992 image of Anna Wintour wearing what Guest of a Guest calls the "worst outfit ever," but Racked National points out the best detail: The caption. Tucked to the right of the photo, it reads, "Vogue's always-warm and jolly editor, Anna Wintour, from the neck up the most stylish woman in America." Did we mention this was before The Devil Wears Prada? [Racked National; GoaG]