Oprah Winfrey's Style Evolution

Skinny jeans, vests and corsets! 25 years of style ups – and downs! – from the Queen of Talk

01 of 26

1986

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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

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.

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