In November of 1988, Anna Wintour had Peter Lindbergh shoot her very first cover as the editor of American Vogue.

The picture of the Israeli model, Michaela Bercu, is nothing like the sharp and clean lines of this month's September issue featuring Lady Gaga.

Bercu is wearing a Christian LaCroix cross emblazoned sweater with a pair of jeans. Her hair is all over the place and her eyes are barely open. In Wintour's September issue letter from the editor, she reflects on the photograph and what it meant for the magazine.

In the moment, she felt it was casual and cool. "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."

Here is Anna Wintour's first cover from November 1988:

november1988cover

And here are some of Anna Wintour's favourite images from Vogue. Go to Vogue.com to see even more:

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  • July 15, 1928

    Photographed by Edward Steichen

  • September 15, 1939

    Photographed by Horst P. Horst

  • May 1, 1947

    Photographed by Irving Penn

  • March 1, 1965

    Photographed by Toni Frissell

  • August 1990

    Photographed by Irving Penn

  • September 1990

    Photographed by Arthur Elgort

  • June 1991

    Photographed by Irving Penn

  • October 1991

    Photographed by Ellen von Unwerth

  • May 1989

    Photographed by Irving Penn

  • November 1988

    Photographed by Peter Lindbergh