Oxford + Park

"It was November 1988, and starred the gorgeous Israeli model Michaela Bercu, photographed by Peter Lindbergh and styled by Carlyne Cerf de Dudzeele. Michaela was wearing an haute couture Christian Lacroix jacket with a beaded cross, all very 'Like a Prayer,' and stonewashed Guess jeans. The jacket was actually part of a suit, but the skirt didn’t fit Michaela; she had been on vacation back home in Israel and had gained a little weight. Not that that mattered. In fact, it only served to reinforce the idea to take couture’s haughty grandeur and playfully throw it headlong into real life and see what happened.

"What none of us expected was to run that picture on the cover, least of all the magazine’s printers, who called up and asked with some consternation, 'Has there been a mistake?' I couldn’t blame them. It was so unlike the studied and elegant close-ups that were typical of Vogue’s covers back then, with tons of makeup and major jewelry. This one broke all the rules. Michaela wasn’t looking at you, and worse, she had her eyes almost closed. Her hair was blowing across her face. It looked easy, casual, a moment that had been snapped on the street, which it had been, and which was the whole point. Afterwards, in the way that these things can happen, people applied all sorts of interpretations: It was about mixing high and low, Michaela was pregnant, it was a religious statement. But none of these things was true. I had just looked at that picture and sensed the winds of change. And you can’t ask for more from a cover image than that."

— Anna Wintour on her first issue of Vogue