Oprah's Crimes Against Fashion

Big hair, bigger shoulder pads—Oprah's worn every trend imaginable. Look back at her "What was I thinking?" wardrobe moments!

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There was also the occasional misguided makeover, like when Oprah dressed up as one of her idols, the legendary Diana Ross. "I feel like a drag queen right now," Oprah said.

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From The Oprah Winfrey Show Oprah's Bloopers, Blunders and Funniest "What Were We Thinking?" Moments

Published on April 14, 2011

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