The style guru opened up about the mortifying meeting during a speech at the Cfda/Vogue Fashion Fund Awards in New York City on Monday (11Nov13), revealing he was caught naked by a fully-clothed Wintour on a nudist beach in Caribbean hotspot St. Barts.
He said, "It was like one of those dreams in high school when everyone has clothes on except you."
Ford also dished out advise to young designers hoping to make it big in the fashion world in front of a crowd, which included Wintour.
Julianne Moore, who starred in Ford's directorial debut A Single Man, introduced Ford to the stage, revealing how he made her feel at ease when they first met in the 1990s just months after she had given birth.
She said, "He was handsome, charming, gracious and absolutely took my breath away. And he assured me that, if I didn't feel comfortable in his dress, that it was fine. He said, 'Wear it, don't wear it - it's just a dress. Don't worry about it.'"