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Oprah Winfrey's Style Evolution (PHOTOS)

Huffington Post     First Posted: 01/29/2012 9:03 am   Updated: 01/30/2012 12:14 pm

Regal is the best way to describe Oprah Winfrey's sensational style. After all, she is the queen of all media.

Billowing ball gowns, sophisticated pant suits and dresses in a kaleidoscope of colors have been her fashion staples. And just like she commanded daytime television for 25 years, Winfrey has owned her personal style with the same confidence and grace.

There have certainly been fashion flubs along the way--mixing prints is always tricky--but Winfrey has shown that she can work the red carpet with just as much pizzazz as her Hollywood friends.

In celebration of her 58th birthday, here's a look at Winfrey's most memorable style moments over the years.

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  • 1987

  • 1989

  • 1992

  • 1995

  • 2002

    WEST HOLLYWOOD, UNITED STATES: US talk show host Oprah Winfrey arrives at the Vanity Fair dinner and post-party celebrating the seventy-fourth Academy Awards, 24 March 2002, at Mortons in West Hollywood, CA. AFP PHOTO/RICH SCHMITT (Photo credit should read RICH SCHMITT/AFP/Getty Images)

  • 2002

    NEW YORK - NOVEMBER 12: Talk show host Oprah Winfrey attends the 46th Annual Equal Opportunity Day Awards Dinner November 13, 2002 at Chelsea Piers in New York City. (Photo by John Falls/Getty Images)

  • 2003

    CAPE TOWN, SOUTH AFRICA - NOVEMBER 27: (UK NEWSPAPERS OUT) Actress and talk show host Oprah Winfrey attends the Thanksgiving Dinner prior to the 46664 concert on November 27, 2003 in Cape Town, South Africa. The concert will take place on November 29th and will benefit the Nelson Mandela Foundation and the fight against AIDS in Africa. Artists performing will include Bono, Queen, Peter Gabriel, The Eurythmics, Beyonce, Youssou N'Dour, and may other internations and African musicians. It will be one of the biggest rock events ever staged in Africa and will also be the most widely distributed media event in history with a potential audience of more than 2 billion people in 166 countries. (Photo by Dave Hogan/Getty Images)

  • 2004

    PASADENA, CA - JANUARY 11: Television Star Oprah Winfrey poses backstage during the 30th Annual People's Choice Awards at the Pasadena Civic Auditorium January 11, 2004 in Pasadena, California. (Photo by Vince Bucci/Getty Images)

  • 2004

    HOLLYWOOD, CA - FEBRUARY 29: Talk show host Oprah Winfrey attends the 76th Annual Academy Awards on February 29, 2004 at the Kodak Theater, in Hollywood, California. (Photo by Carlo Allegri/Getty Images)

  • 2005

    NEW YORK - APRIL 11: Oprah Winfrey arrives to the 2005 Matrix Awards outside the Waldorf-Astoria Hotel on April 11, 2005 in New York. (Photo by Brad Barket/Getty Images)

  • 2005

    SANTA BARBARA, CA - MAY 14: (L - R) Host Oprah Winfrey and US Vogue's Editor at Large Andre Leon Talley attend the Legends Ball at the Bacara Resort and Spa on May 14, 2005 in Santa Barbara, California. (Photo by Frederick M. Brown/Getty Images)

  • 2006

    NEW YORK - JUNE 11: Television personality Oprah Winfrey attends the 60th Annual Tony Awards at Radio City Music Hall June 11, 2006 in New York City, New York. (Photo by Peter Kramer/Getty Images)

  • 2006

    NEW YORK - NOVEMBER 13: Television journalist Barabra Walters poses with honoree Oprah Winfrey at The New York Public Library's Annual Library Lions Gala at The New York Public Library on November 13, 2006 in New York City. (Photo by Evan Agostini/Getty Images)

  • 2007

    WEST HOLLYWOOD, CA - FEBRUARY 25: Television personality Oprah Winfrey arrives at the 2007 Vanity Fair Oscar Party at Mortons on February 25, 2007 in West Hollywood, California. (Photo by Mark Mainz/Getty Images)

  • 2007

    NEW YORK - JUNE 04: Oprah Winfrey attends the 25th Anniversary of the Annual CFDA Fashion Awards held at the New York Public Library on June 4, 2007 in New York City. (Photo by Peter Kramer/Getty Images for CFDA)

  • 2008

    LOS ANGELES, CA - SEPTEMBER 21: TV personality Oprah Winfrey speaks onstage during the 60th Primetime Emmy Awards held at Nokia Theatre on September 21, 2008 in Los Angeles, California. (Photo by Kevin Winter/Getty Images)

  • 2008

    NEW YORK - DECEMBER 03: Oprah Winfrey attends the opening night performance celebrating Alvin Ailey American Dance Theater's 50th anniversary at the New York City Center on December 3, 2008 in New York City. (Photo by Astrid Stawiarz/Getty Images)

  • 2009

    TORONTO, ON - SEPTEMBER 13: Executive producer Oprah Winfrey walks onstage at the 'Precious: Based on the Novel 'Push' by Sapphire' screening introduction during the 2009 Toronto International Film Festival held at Roy Thomson Hall on September 13, 2009 in Toronto, Canada. (Photo by C.J. LaFrance/Getty Images)

  • 2009

    NEW YORK - SEPTEMBER 18: TV personality Oprah Winfrey hosts The Oprah Winfrey Show: Fridays Live From New York at Rumsey Playfield on September 18, 2009 in New York City. (Photo by Michael Loccisano/Getty Images)

  • 2007

    HOLLYWOOD - MARCH 07: Oprah Winfrey presents onstage during the 82nd Annual Academy Awards held at Kodak Theatre on March 7, 2010 in Hollywood, California. (Photo by Kevin Winter/Getty Images)

  • 2010

    NEW YORK - MAY 03: Designer Oscar de la Renta and Oprah attend the Costume Institute Gala Benefit to celebrate the opening of the 'American Woman: Fashioning a National Identity' exhibition at The Metropolitan Museum of Art on May 3, 2010 in New York City. (Photo by Stephen Lovekin/Getty Images)

  • 2010

    CULVER CITY, CA - JUNE 10: Actress Julia Roberts and Oprah Winfrey in the audience during the 38th AFI Life Achievement Award honoring Mike Nichols held at Sony Pictures Studios on June 10, 2010 in Culver City, California. The AFI Life Achievement Award tribute to Mike Nichols will premiere on TV Land on Saturday, June 25 at 9PM ET/PST. (Photo by Christopher Polk/Getty Images for AFI)

  • 2010

    LONG BEACH, CA - OCTOBER 26: Oprah Winfrey is honored with Minerva Award at Maria Shriver Women's Conference at the Long Beach Convention Center on October 26, 2010 in Long Beach, California. (Photo by Frederick M. Brown/Getty Images)

  • 2010

    WASHINGTON, DC - DECEMBER 4: (AFP OUT) Oprah Winfrey, one of the 2010 Kennedy Center honorees, arrives with Stedman Graham for the formal artist's dinner for the Kennedy Center Honors at the United States Department of State December 4, 2010 in Washington, D.C. (Photo by Ron Sachs-Pool/Getty Images)

  • 2010

    SYDNEY, AUSTRALIA - DECEMBER 14: Oprah Winfrey gestures during the first taping of the 'Oprah Winfrey Show' at the Sydney Opera House on December 14, 2010 in Sydney, Australia. 12,000 audience members were selected from 350,000 applicants to participate in two tapings of 'The Oprah Winfrey Show' at the Sydney Opera House. Oprah descended on Australia last week with 302 super fans from the US, Canada and Jamaica to produce four shows for the 25th and final season of the program. the shows will air in the US and Australia in January 2011. (Photo by Brendon Thorne/Getty Images)

  • 2011

    PASADENA, CA - JANUARY 06: Oprah Winfrey arrives at OWN: Oprah Winfrey Network's 2011 TCA Winter Press Tour Cocktail Party at the Horseshoe Gardens at the Langham Hotel on January 6, 2011 in Pasadena, California. (Photo by Frazer Harrison/Getty Images)

  • 2011

    HOLLYWOOD, CA - FEBRUARY 27: Presenter Oprah Winfrey speaks onstage during the 83rd Annual Academy Awards held at the Kodak Theatre on February 27, 2011 in Hollywood, California. (Photo by Kevin Winter/Getty Images)

  • 2011

    CHICAGO, IL - MAY 17: Oprah attends Surprise Oprah! A Farewell Spectacular at the United Center on May 17, 2011 in Chicago, Illinois. (Photo by Daniel Boczarski/Getty Images)

  • 2011

    NEW YORK, NY - OCTOBER 24: Ralph Lauren and Oprah Winfrey attend an evening with Ralph Lauren hosted by Oprah Winfrey and presented at Lincoln Center on October 24, 2011 in New York City. (Photo by Larry Busacca/Getty Images for Ralph Lauren)

  • 2011

    MEYERTON, HENLEY ON KLIP - JANUARY 14: Oprah Winfrey with the Graduates at the inaugural graduation of the class of 2011 at Oprah Winfrey Leadership Academy for Girls on January 14, 2012 in Henley on Klip, South Africa. (Photo by Michelly Rall/Getty Images)

  • Oprah Winfrey Leadership Academy for Girls - Class of 2011 Inaugural Graduation

    MEYERTON, SOUTH AFRICA - JANUARY 14: Oprah Winfrey arrives at the inaugural graduation of the class of 2011 at Oprah Winfrey Leadership Academy for Girls on January 14, 2012 in Henley on Klip, South Africa. (Photo by Michelly Rall/Getty Images)

  • Oprah Winfrey

    U.S. talk show host Oprah Winfrey in an Indian attire greets her fans at the Jaipur Literature Festival in Jaipur, in the western Indian state of Rajasthan, India, Sunday, Jan. 22, 2012. (AP Photo/Manish Swarup)

  • US talk show host Oprah Winfrey gestures

    US talk show host Oprah Winfrey gestures towards the media as she walks down a lane in Mumbai on January 17, 2012. Winfrey is on her first visit to the country to film an episode of her new talk show, 'Oprah’s Next Chapter', and is expected to attend a literary festival in Jaipur city. AFP PHOTO/Indranil MUKHERJEE (Photo credit should read INDRANIL MUKHERJEE/AFP/Getty Images)

  • Oprah Winfrey

    Oprah Winfrey poses with her honorary Oscar at the 84th Academy Awards on Sunday, Feb. 26, 2012, in the Hollywood section of Los Angeles. (AP Photo/Chris Carlson)

  • David Letterman, Oprah Winfrey

    FILE - This Nov. 26, 2012 file photo shows Ball State University alumnus David Letterman, right, host of CBS's "Late Show," with Oprah Winfrey following an interview at Ball State University in Muncie, Ind. Letterman says he sees a psychiatrist once a week, part of his attempt to be the person he once believed he was. The late-night talk show host gave an extraordinary interview to Oprah Winfrey, where he talked about his feuds with her and Jay Leno and his own effort to make amends for the affairs that became public three years ago when a man tried to extort him. (AP Photo/Michael Conroy, file)

  • In this image released by CBS, Oprah Winfrey appears on "CBS This Morning," with co-host Charlie Rose, Monday, April 2, 2012 in New York. Winfrey says she still has faith in her troubled cable network. Appearing on the morning show, Winfrey told the show's co-host _ and her best friend _ Gayle King that she believes the Oprah Winfrey Network will fulfill its mission of transforming viewers' lives. But if viewers don't respond, Winfrey says: “I will move on to the next thing.” OWN has struggled to build an audience since its launch in January 2011. (AP Photo/CBS, Heather Wines)

  • Oprah Winfrey

    Oprah Winfrey attends the premiere of "Beyonce: Life Is But A Dream" at the Ziegfeld Theatre on Tuesday, Feb. 12, 2013 in New York. (Photo by Evan Agostini/Invision/AP)

  • 6th Annual ESSENCE Black Women In Hollywood Awards Luncheon - Arrivals

    BEVERLY HILLS, CA - FEBRUARY 21: Oprah Winfrey attends the Sixth Annual ESSENCE Black Women In Hollywood Awards Luncheon at Beverly Hills Hotel on February 21, 2013 in Beverly Hills, California. (Photo by Frederick M. Brown/Getty Images)

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Regal is the best way to describe Oprah Winfrey's sensational style. After all, she is the queen of all media. Billowing ball gowns, sophisticated pant suits and dresses in a kaleidoscope of color...
Regal is the best way to describe Oprah Winfrey's sensational style. After all, she is the queen of all media. Billowing ball gowns, sophisticated pant suits and dresses in a kaleidoscope of color...
 
 
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07:45 PM on 01/30/2012
A billion dollars could change all of us in ways that we ould never imagine.
07:41 PM on 01/30/2012
I love seeing Oprah without makeup on, hair stylies doing her hair and wearing rgular clothes like you and me and guess what - she looks ordinary just like you and me. Money doesn't buy everthing especially when you take the makeup and clothes off.
07:22 PM on 01/30/2012
No matter how thin or heavy Oprah is, she always looks elegant....unlike Michelle Obama
HUFFPOST SUPER USER
pcs5141
cut the crap
06:56 PM on 01/30/2012
Is'nt that a picture Homie D. Clown ????????
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08:18 PM on 01/30/2012
That's an excellent observation. She has that clown look; like when Katie Couric smiles, she looks like The Joker!
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Dental Trader
06:51 PM on 01/30/2012
If you watch her first 100 episodes and compare them to The Merv Griffin Show, you will see a mirror image. The interviews, timing, expressions and her responses (right down the inflextion of her voice) are identical. Clearly her producer set this up for the then weathergirl who had no clue how to interview. She's Black Merv! How hysterical is that? Typical Hollyweird let's format everything crap.
06:34 PM on 01/30/2012
Is that her nose or a 2 car garage?
photo
HUFFPOST SUPER USER
Ebusafrica
Pet hate? haters
02:59 AM on 02/01/2012
The internet comment thread has become an avenue for weak lilly livered, sad, despressed, insecure people to vent their self hate masked as inconsequential attacks on people that will never ever know they exist... and you are one of them.
06:17 PM on 01/30/2012
Another left-wing, progressive 'star'??????
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06:18 PM on 01/30/2012
another sad sad person got to,jut got to bring up politics in anything.im guessing thats just all some have going on in their lives
photo
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Dean M Miller
I Feed On The Tears Of Liberals
07:49 PM on 01/30/2012
"another sad sad person got to,jut got to bring up politics" lol

u didnt have enough spelling class in your life ha
06:28 PM on 01/30/2012
What'd ya say?!?!?!?
06:00 PM on 01/30/2012
She hates whites
06:00 PM on 01/30/2012
Ohhhhh Oprah farted Yea Yea Yea
This comment has been removed due to violations of our [Guidelines]
05:24 PM on 01/30/2012
She hurts my eyes today as much as she did back them.
04:51 PM on 01/30/2012
Happy Birthday Oprah! We love you. You are such an inspiration to many of us. May God Bless you.
06:33 PM on 01/30/2012
BS
04:15 PM on 01/30/2012
that picture is so unbecoming, sorry but its alfulllllllllll
04:15 PM on 01/30/2012
She has come a long way for being so oppressed by white people.
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06:39 PM on 01/30/2012
LOL
04:03 PM on 01/30/2012
Oprah has always been one of my favorite people. I hardly ever missed her show, some I just didn't want to watch and didn't. Most of her clothes are great, but when you can afford to buy them and have people to dress you it is easy. The only time I didn't like her style was when she had her hair very curly, which was ok, but it was so far forward on her face that it ruined the look. Oprah has such a beautiful face that she needs to show it off, and she does have great hair! I should be so lucky! Keep it up Oprah! I don't always agree with her, but everyone is entitled to their own opinion and ideas!