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8. Mad Men-Inspired Dress
In 2009, The Oprah Show celebrated the swinging '60s with the stars of Mad Men. Kelly worked with Emmy award-winning costume designer Janie Bryant to design this pink dress for Oprah. "This was such a fun collaboration with the costume designer," Kelly says. "The 1960s silhouette is actually perfect for Oprah's shape."
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LONG FORM
ONE WORD