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Unexpected Moments

Even Oprah breaks her style rules sometimes! When the talk show queen wants to step out of her comfort zone, she goes for ladylike separates in springtime shades (left), eye-catching prints, and bold bright hues like safety-cone orange.

Oprah attended New York Public Library's 6th Annual Library Lions gala in 2006.

(CREDIT: Don Arnold/WireImage)
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