By Suzanne Zuckerman
May 17, 2010 12:00 PM


When Oprah Winfrey learned she’d be cochairing this year’s Met Costume Institute Gala last year, she knew whom to call for her dress. “Oscar!” she said, pointing to her date for the evening. “It’s a double O team here!” The discussions had begun when, at de la Renta’s request, Winfrey sent him photos of herself in gowns she found flattering. Two hundred and fifty hours, four dressmakers, three fittings and “hundreds and hundreds of ruffles” later, the designer said he had created “a queen of the night gown” with dramatic cleavage and “an embroidered bodice that fits her like a glove.” The night before the gala, Winfrey and de la Renta shared a “cozy” dinner at the New York home of Vogue editor Anna Wintour. There, Oprah told Oscar about the jewels from her own collection that she planned to wear. “She told me she feels good about her diamonds,” he recalled. “She said, ‘I pay for them with my work.’ There was no prima donna attitude. On the contrary.” Diamonds or not, “her personality, which is what makes her so successful, cannot be outshined.”