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November 1988, the first Vogue cover under Anna Wintour's editorship. Back then, it was much easier to make a statement—and yes, this cover caused a real sensation. Model Michaela Bercu posed in a couture Christian Lacroix sweater with a cross, paired with worn Guess jeans. It was the first time jeans had ever appeared on the cover of the magazine. Photographed by Peter Lindbergh. FirstPass