Oprah in Valentino and Tuleh

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4. Valentino Top and Tuleh Skirt
In the past, Kelly says Oprah didn't like to mix different designers within the same outfit—but this Valentino top with pearl accent and sequined Tuleh skirt is her favorite example of designers working in harmony. "I loved these two together," Kelly says. "The fit and flair of the skirt is a great silhouette."