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This all-white fringe and fur Golden Globes ensemble is not one of O's favorite things: "When I see old photos of myself, I really don't know what I was thinking," she has said. "Somebody should have stopped me!"
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She was a year into her national talk show career but Winfrey looked more like a Dynasty super-fan than a host, complementing her beaded look with some pomp and circumstance.
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Skinny jeans and all! Winfrey famously whittled herself down to her smallest size ever with daily runs and an all-liquid diet, proudly showing off her form in curve-hugging size 10 jeans and a fitted turtleneck.
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The host with the most struck a playful stance in a structural metallic jacket with rock-solid shoulder pads and jacquard skirt.
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Ample décolletage, a defined waist – and Stedman: Winfrey's go-to style took shape at a 1990 awards show.
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Hey, it was the '90's! The star still manages to look stylish while epitomizing the era's fashions in a color-blocked suit.
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The emerging fashionista pairs soaring ratings with geometrics, striking a pose in a black-and-white skirt suit and two-tone pumps.
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She is in the Golden State, after all! The star gets sunny at a television executives convention in San Francisco in a vivid top and printed vest.
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A slimmed-down Oprah highlights her hourglass shape in a floral corset gown at the 1994 Emmy Awards, where she takes home the trophy for outstanding talk show host.
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Winfrey sweeps into the tony scene at the 67th annual Academy Awards wearing a silky cocoa gown with a billowing train.
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The very next year, the star offsets a figure-flattering navy blue gown with a gilt shawl fit for a queen at the Oscars.
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The fashion plate gives some pointers in understated dressing, pairing a sleek dress coat with bow-tied heels at the 1997 premiere of her TV drama Before Women Had Wings.
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Winfrey strikes a familiar pose in a fashion forward kimono draped over a peekaboo gown at the L.A. premiere of Beloved.
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The queen of talk keeps her figure under wraps – but can't resist a hint of lace – while being honored at the 1999 National Book Awards.
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Go big or go home! Winfrey takes on Y2K with trademark panache, pairing a bright suit with a matching clutch and sandals.
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Is it green or is it orange? The Color Purple star keeps us guessing in an iridescent two-piece gown and matching shawl in at a event for her magazine, O.
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What a bombshell! Winfrey looks sleek and timeless in a long-sleeved white column dress and metallic heels at a charity ball.
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Oprah embraces a bubblegum-hued three-piece suit – and bare feet! – at an AIDS awareness event in Cape Town, South Africa.
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Continuing her appreciation for luxe fabrics, Winfrey selects a gray Gianfranco Ferré gown for the 76th annual Academy Awards. "Let's get your breasts in place," she quips before introducing Mystic River.
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You go, O! At the next year's Oscars, Winfrey is a vision in a hand-embroidered Vera Wang stunner. "Gold is good with my complexion," she says of the hue.
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To celebrate her magazine O's continued success, Oprah steps out in a get-noticed red sheath, matching d'Orsay heels and a radiant smile.
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Winfrey brightens up the red carpet in a vivid Gucci kimono gown at that year's Vanity Fair Oscar party.
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An admittedly heavier Oprah opts for a subdued look, pairing an elegant charcoal wrap dress with graphite heels.
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For last year's Met Ball, the evening's co-host arrived on the scene in a navy silk organza Oscar de la Renta gown with a voluminous skirt.
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O my – 25 years and she's still got it! The star made a radiant turn at the 83rd annual Academy Awards in an ombré sequined show-stopper from Zac Posen.