Oprah Winfrey's Style Evolution
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.
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.
The host with the most struck a playful stance in a structural metallic jacket with rock-solid shoulder pads and jacquard skirt.
Ample décolletage, a defined waist – and Stedman: Winfrey's go-to style took shape at a 1990 awards show.
Hey, it was the '90's! The star still manages to look stylish while epitomizing the era's fashions in a color-blocked suit.
The emerging fashionista pairs soaring ratings with geometrics, striking a pose in a black-and-white skirt suit and two-tone pumps.
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.
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.
Winfrey sweeps into the tony scene at the 67th annual Academy Awards wearing a silky cocoa gown with a billowing train.
The very next year, the star offsets a figure-flattering navy blue gown with a gilt shawl fit for a queen at the Oscars.
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.
Winfrey strikes a familiar pose in a fashion forward kimono draped over a peekaboo gown at the L.A. premiere of Beloved.
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.
Go big or go home! Winfrey takes on Y2K with trademark panache, pairing a bright suit with a matching clutch and sandals.
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.
What a bombshell! Winfrey looks sleek and timeless in a long-sleeved white column dress and metallic heels at a charity ball.
Oprah embraces a bubblegum-hued three-piece suit – and bare feet! – at an AIDS awareness event in Cape Town, South Africa.
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.
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.
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.
Winfrey brightens up the red carpet in a vivid Gucci kimono gown at that year's Vanity Fair Oscar party.
An admittedly heavier Oprah opts for a subdued look, pairing an elegant charcoal wrap dress with graphite heels.
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.
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.