Oprah in Citizens of Humanity Jeans

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10. Cesare Paciotti Sweater and Citizens of Humanity Jeans
During one 2004 taping, Oprah kept it casual in a Cesare Paciotti sweater and Citizens of Humanity jeans. "Oprah used to say 'no jeans after 40,' but we changed her mind," Kelly says. "I think she looked young, fun and still appropriate."