Style & Beauty

Oprah Winfrey's Style Evolution, From So '80s To Ultra Glam

The TV mogul has never been afraid to go bold, especially on the red carpet.

Oprah Winfrey has always had a bold personality and personal style to match.

Since the 1970s, the media mogul has been appearing on television screens across the country, making her one of the most famous faces in America. She’s also appeared in films, won countless awards and honors, and she’s one of three black billionaires on Forbes’ list of the world’s billionaires.

On top of all that, Winfrey has become a red carpet staple, gracing award shows and openings with her own brand of glamour. Since the early days of her career, the star has gravitated toward some pretty bold looks. In the ’80s, it was all about shoulder pads, patterns and sparkling embellishment. In the ’90s and ’00s, we saw the star opt for plenty of monochromatic looks that were equally as striking. We should also note that Winfrey sure knows how to rock a red carpet gown.

Below, take a look at her changing style through the years, just in time to celebrate her 65th birthday on Jan. 29.

1984
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Oprah Winfrey, then host of "AM Chicago," poses on State Street in 1984.
January 1986
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Winfrey attends the rehearsals for the 43rd Annual Golden Globe Awards on Jan. 23, 1986, at the Beverly Hilton Hotel in Beverly Hills.
March 1986
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Winfrey attends the nominees luncheon for the 58th annual Academy Awards on March 13, 1986, at the Beverly Hilton Hotel in Beverly Hills.
November 1986
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Winfrey spotted on Nov. 7 at Tramp's in Beverly Hills, California.
December 1986
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Winfrey attends the premiere of "Native Son" on Dec. 8, at the Apollo Theater in New York City.
1987
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Winfrey and Dolly Parton on "Dolly" in 1987.
March 1987
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Winfrey attends the 59th Academy Awards.
1987
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Winfrey holds an Emmy statue at the 14th annual Daytime Emmy Awards.
December 1987
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Winfrey and Stedman Graham attend the premiere of "Good Morning, Vietnam" on Dec. 17, at Cinerama Dome Theater in Hollywood.
February 1989
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Winfrey attends the premiere of "The Woman of Brewsters Place" on Feb. 17, at Director's Guild Theater in Hollywood.
February 1989
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Winfrey attends the 9th Annual National Conference for Women at New York Hilton Hotel in New York City.
September 1989
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Graham and Winfrey attend the 15th Annual Rape Treatment Center Brunch on Sept. 24, at Sandra Moss in Holmby Hills, California.
January 1993
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Winfrey attends the NAPTE Convention at the Moscone Convention Center in San Francisco, California.
May 1993
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Winfrey attends the 20th annual Daytime Emmy Awards at Marriott Marquis Hotel in New York City.
1995
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Winfrey attends an event with her partner Stedman Graham circa 1995 in Los Angeles.
March 1995
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Oprah Winfrey during the 67th Academy Awards in Los Angeles.
1995
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Winfrey and Graham attend the Essence Awards at the Paramount Theater in New York City.
May 1996
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Winfrey and Graham attend 21st Annual Daytime Emmy Awards on May 25, at Radio City Music Hall in New York City.
March 1996
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Winfrey at The International Radio and TV Foundation Gold Medal award dinner at the Waldorf-Astoria Hotel in New York City.
1996
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Winfrey at the Giorgio Armani Store in New York City.
2000
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Winfrey walks her dogs in front of a New York City hotel before she gets into her limo on Sept. 29.
September 2002
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Winfrey attends the 54th Annual Primetime Emmy Awards at the Shrine Auditorium on Sept. 22, 2002 in Los Angeles.
March 2002
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Winfrey attends the Vanity Fair Oscar Party at Mortons on March 24, in West Hollywood.
November 2002
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Winfrey at the 12th Annual Broadcasting & Cable Magazine Hall of Fame Gala at the Marriott Marquis in New York City, Nov. 11.
January 2004
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Winfrey poses backstage during the 30th Annual People's Choice Awards at the Pasadena Civic Auditorium Jan. 11, in Pasadena, California.
February 2004
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Winfrey attends the 76th Annual Academy Awards at the Kodak Theater on Feb. 29, in Hollywood.
February 2005
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Winfrey arrives at the 77th annual Academy Awards in Los Angeles.
April 2005
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Winfrey arrives to the 2005 Matrix Awards outside the Waldorf-Astoria Hotel on April 11, in New York.
June 2006
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Winfrey attends the 60th Annual Tony Awards at Radio City Music Hall June 11, in New York City.
February 2007
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Winfrey arrives at the 2007 Vanity Fair Oscar Party at Mortons on Feb. 25, in West Hollywood.
June 2008
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Winfey arrives at the dinner in honor of Nelson Mandela on his 90th birthday at Hyde Park June 25, in London.
December 2008
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Winfrey attends the opening night after party celebrating Alvin Ailey American Dance Theater's 50th anniversary at the New York City Center on Dec. 3.
September 2009
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Winfrey attends the "Precious" premiere at the Roy Thomson Hall during the 2009 Toronto International Film Festival on Sept. 13, in Toronto, Canada.
May 2010
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Designer Oscar de la Renta and Winfrey 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, in New York City.
December 2010
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Winfrey, one of the 2010 Kennedy Center honorees, with Graham for the formal artist's dinner for the Kennedy Center Honors at the United States Department of State Dec. 4, in Washington, D.C.
December 2010
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Winfrey poses at The Royal Botanic Gardens on Dec. 11, in Sydney, Australia.
March 2012
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Winfrey attends the 3rd annual Diane Von Furstenberg awards at the United Nations on March 9, in New York City.
August 2013
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Graham and Winfrey attend "The Butler" premiere at Ziegfeld Theater on Aug. 5, in New York City.
January 2014
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Winfrey and David Oyelowo at the 20th Annual Screen Actors Guild Awards at The Shrine Auditorium on Jan. 18, in Los Angeles.
January 2014
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Winfrey attends the 19th Annual Critics' Choice Awards at Barker Hangar on Jan. 16, in Santa Monica.
February 2015
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Winfrey attends the 2015 Film Independent Spirit Awards at Santa Monica Beach on Feb. 21, in Santa Monica.
February 2015
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Winfrey arrives at the 87th Annual Academy Awards at Hollywood & Highland Center on Feb. 22, in Hollywood.
April 2016
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The TV mogul attends the Tribeca Tune In: Greenleaf at BMCC John Zuccotti Theater on April 20, in New York City.
April 2017
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Winfrey attends "The Immortal Life of Henrietta Lacks" premiere at SVA Theater on April 18, in New York City.
January 2018
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Winfrey poses with the Cecil B. DeMille Award in the press room during The 75th Annual Golden Globe Awards at The Beverly Hilton Hotel in Beverly Hills, California.
March 2018
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The TV personality attends the 2018 MoMA David Rockefeller Award Luncheon Honoring Oprah at The Ziegfeld Ballroom on March 6, in New York City.
December 2018
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Winfrey wears a Gert-Johan Coetzee dress onstage during the Global Citizen Festival: Mandela 100 at FNB Stadium on Dec. 2, in Johannesburg, South Africa.
Oprah's Favorite Things 2018