She can afford the best stylist money can buy, but that's not to say Oprah Winfrey hasn't had her fair share of fashion misses (along with a great deal of hits) over her extensive career.
Pics: Two Looks, One Star!
Join us as we look back at Lady O's changing styles through the years!
Oprah Winfrey Fashion Flashback
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Oprah Winfrey Fashion Flashback
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Oprah Winfrey Fashion Flashback
