Following the debut of her Emmy-winning talk show in 1986, Oprah Winfrey spun her hosting career into a series of successful endeavors in television, film and editorial, earning her the nickname “Queen of All Media.”
Through the years, Winfrey’s style has been defined by designers like Carolina Herrera, Vera Wang and Ralph Lauren — the latter of whom she interviewed during the final season of “The Oprah Winfrey Show.” In 2023, Winfrey notably embraced method dressing, promoting her film “The Color Purple” in a series of custom violet looks, including gowns by Louis Vuitton and Prada. At the 2024 Democratic National Convention, Winfrey continued her purple streak, selecting a plum-colored suit by Christian Siriano.
Ahead, look back at Winfrey’s best style moments through the years, including exclusive photos from the WWD archives.
-
Oprah Winfrey’s Style Through the Years: 1998
Image Credit: WWD Oprah Winfrey arrives for the premiere of her production of Toni Morrison’s “Beloved” in 1998.
-
Oprah Winfrey’s Style Through the Years: 2000
Image Credit: WWD Oprah Winfrey launches O Magazine in New York in 2000.
-
Oprah Winfrey’s Style Through the Years: 2001
Image Credit: Fairchild Archive/Penske Media Oprah Winfrey attends the 2001 Emmy Awards in Los Angeles.
-
Oprah Winfrey’s Style Through the Years: 2004
Image Credit: Fairchild Archive/Penske Media Oprah Winfrey and Nicole Kidman attend Vanity Fair’s 2004 Oscars party in Los Angeles.
-
Oprah Winfrey’s Style Through the Years: 2005
Image Credit: Donato Sardella Halle Berry and Oprah Winfrey attend the 2005 Academy Awards in Los Angeles. Berry is wearing Atelier Versace and Winfrey is wearing Vera Wang.
-
Oprah Winfrey’s Style Through the Years: 2006
Image Credit: Fairchild Archive/Penske Media Oprah Winfrey attends the New York Public Library’s 2006 Literary Lions gala.
-
Oprah Winfrey’s Style Through the Years: 2007
Image Credit: Fairchild Archive/Penske Media Oprah Winfrey attends Vanity Fair’s 2007 Oscars party in Los Angeles.
-
Oprah Winfrey’s Style Through the Years: 2007
Image Credit: NYT Syndicate Ralph Lauren and Oprah Winfrey arrive at the 2007 Council of Fashion Designers of America Awards at the New York Public Library.
-
Oprah Winfrey’s Style Through the Years: 2008
Image Credit: Fairchild Archive/Penske Media Oprah Winfrey attends the Alvin Ailey 50th Anniversary party at New York City Center in 2008.
-
Oprah Winfrey’s Style Through the Years: 2010
Image Credit: Fairchild Archive/Penske Media Karl Lagerfeld and Oprah Winfrey attend the 2010 Met Gala.
-
Oprah Winfrey’s Style Through the Years: 2010
Image Credit: Fairchild Archive/Penske Media Gayle King and Oprah Winfrey attend the New York Women in Communications 2010 Matrix Awards at the Waldorf-Astoria.
-
Oprah Winfrey’s Style Through the Years: 2011
Image Credit: Fairchild Archive/Penske Media Oprah Winfrey hosts An Evening With Ralph Lauren in New York in 2011.
-
Oprah Winfrey’s Style Through the Years: 2014
Image Credit: Fairchild Archive/Penske Media Oprah Winfrey attends the 2014 Screen Actors Guild Awards in Los Angeles.
-
Oprah Winfrey’s Style Through the Years: 2018
Image Credit: Andrew H Walker/WWD Oprah Winfrey attends the CFDA Fashion Awards in New York in 2018.
-
Oprah Winfrey’s Style Through the Years: 2024
Image Credit: The Hollywood Reporter via Getty Oprah Winfrey attends the 81st Annual Golden Globe Awards in January.
-
Oprah Winfrey’s Style Through the Years: 2024
Image Credit: Variety via Getty Images Oprah Winfrey at the 55th NAACP Image Awards in March.
-
Oprah Winfrey’s Style Through the Years: 2024
Image Credit: AFP via Getty Images Oprah Winfrey at the Democratic National Convention in August.