Anna Wintour has had a long history as Vogue's editor-in-chief, a role she's held since 1988. So while she's kept things pretty safe with her fashion choices since then (we can prove it -- check it out here), she has spent the past two decades taking risks for the magazine.
Further proving her pop culture relevance, Wintour will appear on CBS this weekend chatting with Hamish Bowles on "CBS Sunday Morning." We will certainly be watching -- er, DVR-ing -- but we also got a sneak peek this morning from Women's Wear Daily.
One topic that comes up is risk-taking covers -- and all those celebrities. Wintour says:
"I remember getting quite a bit of criticism for my first Madonna cover... And you know, 'She'll never sell.' And it was a little bit risky. And it was up something extraordinary, like 40 percent on newsstands. So that was an eye-opener to all of us."
It taught everyone a lesson, of course: celebrities sell. And they have continued to do so since that early revelation, as Vogue is one of the most celeb-clogged of all the international Vogue editions (compared to, say, Vogue Italia or Vogue Paris).
Ironically, now Wintour herself has become a celebrity, renowned for her famous bob and dark shades as well as her involvement with Fashion's Night Out and her tacitly implied inspiration for the film "The Devil Wears Prada."
She's famous enough, in fact, to get her own segment of television on CBS. Watch on Sunday and read more of the preview at WWD.com -- and below, take a peek into Anna Wintour's fashion past.