People.com Celebrity Oprah Winfrey's Style Evolution Skinny jeans, vests and corsets! 25 years of style ups – and downs! – from the Queen of Talk By Justine Harman Published on May 17, 2011 12:00 PM Share Tweet Pin Email 01 of 26 1986 Ralph Dominguez/Globe 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!" 02 of 26 1987 Bob Michelson/Globe 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. 03 of 26 1988 Charles Bennet/AP 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. 04 of 26 1989 John Paschal/Celebrity Photo The host with the most struck a playful stance in a structural metallic jacket with rock-solid shoulder pads and jacquard skirt. 05 of 26 1990 Scott Downie/Celebrity Photo Ample décolletage, a defined waist – and Stedman: Winfrey's go-to style took shape at a 1990 awards show. 06 of 26 1991 Mark Reinstein/IPOL/Globe Hey, it was the '90's! The star still manages to look stylish while epitomizing the era's fashions in a color-blocked suit. 07 of 26 1992 John Paschal/Celebrity Photo The emerging fashionista pairs soaring ratings with geometrics, striking a pose in a black-and-white skirt suit and two-tone pumps. 08 of 26 1993 Ron Galella/WireImage 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. 09 of 26 1994 Jim Smeal/WireImage 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. 10 of 26 1995 Ron Wolfson/Landov Winfrey sweeps into the tony scene at the 67th annual Academy Awards wearing a silky cocoa gown with a billowing train. 11 of 26 1996 Lisa Rose/Globe The very next year, the star offsets a figure-flattering navy blue gown with a gilt shawl fit for a queen at the Oscars. 12 of 26 1997 Peter Brooker/Rex USA 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. 13 of 26 1998 Eric Charbonneau/BEImages Winfrey strikes a familiar pose in a fashion forward kimono draped over a peekaboo gown at the L.A. premiere of Beloved. 14 of 26 1999 Arnaldo Magnani/Getty 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. 15 of 26 2000 Lawrence Schwartzwald/Liaison/Getty Go big or go home! Winfrey takes on Y2K with trademark panache, pairing a bright suit with a matching clutch and sandals. 16 of 26 2001 Jennifer Graylock/Fashion Wire Daily 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. 17 of 26 2002 Kevin Winter/Getty What a bombshell! Winfrey looks sleek and timeless in a long-sleeved white column dress and metallic heels at a charity ball. 18 of 26 2003 Dave Benett/Getty Oprah embraces a bubblegum-hued three-piece suit – and bare feet! – at an AIDS awareness event in Cape Town, South Africa. 19 of 26 2004 Axelle/Bauer-Griffin 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. 20 of 26 2005 Hahn/Khayat/Nebinger/Abaca 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. 21 of 26 2006 Michael Loccisano/FilmMagic 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. 22 of 26 2007 Jeffrey Mayer/WireImage Winfrey brightens up the red carpet in a vivid Gucci kimono gown at that year's Vanity Fair Oscar party. 23 of 26 2008 Jon Kopaloff/FilmMagic An admittedly heavier Oprah opts for a subdued look, pairing an elegant charcoal wrap dress with graphite heels. 24 of 26 2009 Jamie McCarthy/WireImage Winfrey's fuchsia shift is as bright as her smile when surprised by Hugh Jackman and Daniel Craig while filming her show live in N.Y.C.'s Central Park. 25 of 26 2010 Billy Farrell/Patrick McMullan/Sipa 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. 26 of 26 2011 Kevin Winter/Getty 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.