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Oprah Winfrey Says Anna Wintour Pushed Her to Lose Weight for Vogue Cover

Oprah Winfrey has spent decades being judged for her weight—but she’s done being shaped by it.

In a candid new interview with People, the 71-year-old media mogul reflected on the intense scrutiny she faced at the height of early-2000s diet culture, including pressure from fashion’s most powerful gatekeepers. Winfrey confirmed that Vogue editor-in-chief Anna Wintour, 76, encouraged her to lose weight before appearing on the magazine’s cover in 1998.

Oprah Winfrey greets the audience during the opening show of Oprah 'In Conversation' Australia 2025 tour. / Don Arnold / Getty Images

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