The East Nashville High School student modeled a perfect flip when she was named Miss WVOL.
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1986
Winfrey cropped her coif and added face-framing layers.
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March 13, 1986
The future TV titan rocked a short, wavy style at the 58th Annual Academy Awards in Beverly Hills.
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1980s
The talk show host teased her hair to gravity-defying heights.
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1990
The Beloved actress got layered bangs.
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1992
Weighing 237 pounds -- her heaviest ever -- Winfrey teased her layered bob.
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1997
Winfrey sported a shaggy cropped style.
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October 8, 1998
The Color Purple actress debuted longer, straighter locks.
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March 24, 2002
Winfrey returned to her iconic shorter hairstyle, which featured layered bangs and a shaggy bottom.
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February 29, 2004
At the 76th Academy Awards in Beverly Hills, Winfrey unveiled a longer cut with flipped tips.
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June 2, 2004
Winfrey opted for voluminous curls at Sesame Workshop's 2nd Annual Benefit Gala in New York City.
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October 23, 2004
The future OWN creator sported messy curls at the 16th Annual Carousel of Hope Gala in Beverly Hills.
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May 14, 2005
Sporting longer locks, Winfrey straightened her hair and curled her tips at the Legends Ball in Santa Barbara, Calif.
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July 13, 2005
Winfrey unveiled a chic, sleek bob at the 13th Annual ESPY Awards in Hollywood.
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August 12, 2006
Pulling her natural curls into a loose ponytail, Winfrey visited prospective students at her Leadership Academy in Durban, South Africa.
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October 9, 2006
With tints of red in her mane, the media mogul wore her hair in a casual half-up, half-down style.
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January 2, 2007
Sporting caramel-colored highlights, Winfrey wore her hair in loose curls while opening her Leadership Academy for Girls in Henley-on-Klip, South Africa.
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February 25, 2007
The daytime talk show host looked radiant wearing voluminous spiraling curls at the Vanity Fair Oscar party in Hollywood.
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September 13, 2009
Winfrey pulled her jet black hair into a high ponytail at the Precious premiere in Toronto.
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September 2012
Winfrey showed off her natural curls on the cover of O, The Oprah Magazine.
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