Oprah Winfrey wears a blush pink sweater and pleated skirt to interview Prince Harry and Meghan Markle for a CBS interview on March 7, 2021. Courtesy OSN
Oprah Winfrey wears a floral brooch to speak at a podium early in her career, during her time at WJZ, Baltimore, Maryland on January 20, 1978. Getty Images
Oprah Winfrey wears layered neutral knitwear and statement earrings to host 'AM Chicago' in 1984. Getty Images
Oprah Winfrey wears a white fringed gown and fur shawl to attend the 43rd Annual Golden Globe Awards on January 24, 1986 at the Beverly Hilton Hotel in Beverly Hills, California. Getty Images
Oprah Winfrey wears a white dress with gold detailing to attend 58th Annual Academy Awards with Akosua Busia on March 24, 1986 at the Dorothy Chandler Pavilion in Los Angeles, California. Getty Images
Oprah Winfrey wears a black fur coat to attend the premiere of 'Native Son' at the Apollo Theatre, New York City on December 8, 1986. Getty Images
Oprah Winfrey wears a black and gold sequinned dress to appear on 'Dolly' with Dolly Parton in 1987. Getty Images
Oprah Winfrey wears a black gown with sequinned detailing to attend the 59th Annual Academy Awards with Stedman Graham on March 30, 1987. Getty Images
Oprah Winfrey wears a red jacket over a black buttoned dress to attend the 14th Annual Daytime Emmy Awards on June 30, 1987. Getty Images
Oprah Winfrey wears a light brown fur coat to attend the 'Good Morning, Vietnam' premiere with Stedman Graham in Los Angeles, California on December 17, 1987. Getty Images
Oprah Winfrey wears a gold jacket with shoulder pads and jacquard skirt to attend the premiere of 'The Woman of Brewsters Place' at the Director's Guild Theatre in Hollywood, California on February 17, 1989. Getty Images
Opray Winfrey wears yellow and black tailoring to attend the 19th Annual Daytime Emmy Awards on June 23, 1992. Getty Images
Oprah Winfrey wears a pink floral corseted dress to attend the Daytime Emmy Awards on May 1, 1994. Getty Images
Oprah Winfrey wears a metallic purple two-piece to attend the 21st Annual Daytime Emmy Awards with Steadman Graham on May 25, 1994. Getty Images
Oprah Winfrey wears a dusty pink two-piece suit to attend the 'One Smart Lady' Ladies Home Journal Awards on November 11, 1994. Getty Images
Oprah Winfrey wears a brown silk gown with a taffeta train to attend the 67th Academy Awards in Los Angeles, California on March 27, 1995. FilmMagic
Oprah Winfrey wears a full light-blue skirt with a silver top to attend the 1995 Essence Awards with Stedman Graham at the Paramount Theatre in New York City on May 12, 1995. Getty Images
Oprah Winfrey wears an orange jacket during a segment on the 'The Oprah Winfrey Show' with Hillary Clinton in Chicago, Illinois on May 16, 1995. AFP
Oprah Winfrey, in head-to-toe red, attends The International Radio and TV Foundation Gold Medal award Dinner at the Waldorf Astoria Hotel in New York on March 21, 1996. Getty Images
Oprah Winfrey wears a navy gown with a gold shawl to attend the 68th Annual Academy Awards on March 25, 1996. Getty Images
Oprah Winfrey wears a black suit to attend the 'Before Women Had Wings' premiere in West Hollywood, California on October 20, 1997. Getty Images
Oprah Winfrey wears a red-and-black gown to attend 'Ebony Magazine' Celebrate the Dream: 50 Years of Ebony Magazine event on November 17, 1997. Getty Images
Oprah Winfrey wears a black dress with a metallic silver shawl to attend the 'Beloved' premiere on October 8, 1998. Getty Images
Oprah Winfrey wears a bronze two-piece to attend the 24th Annual People's Choice Awards with Stedman Graham on November 1, 1998. Getty Images
Oprah Winfrey wears an iridescent green and pink gown to attend the first anniversary party for 'O Magazine' in New York City on April 17, 2001. Getty Images
Oprah Winfrey wears a white shirt and trouser set on 'The Oprah Winfrey Show' with Stevie Wonder, John Travolta, Gayle King and Tina Turner in Chicago on January 29, 2004. EPA
Oprah Winfrey wears blue Gianfranco Ferre to attend the 76th Annual Academy Awards in Hollywood California on February 29, 2004. EPA
Oprah Winfrey wears a lilac dress with matching accessories to officiate at the Nobel Peace Prize Concert with actor Tom Cruise in Oslo, Norway on December 11, 2004. EPA
Oprah Winfrey wears a pink collared dress to meet pupils who have enrolled in her school in Henley-on-Klip, South Africa, on January 2, 2007. EPA
Oprah Winfrey wears co-ordinated shades of brown to attend a Barack Obama campaign rally in Iowa on December 8, 2007. EPA
Oprah Winfrey wears a white shirt with a pleated black skirt to attend a dinner in honour of Nelson Mandela's 90th birthday in London on June 25, 2008. Getty Images
Oprah Winfrey wears a green rain coat in Copenhagen, Denmark on September 20, 2009. EPA
Oprah Winfrey wears an orange shift dress to arrive at Amalienborg Castle, Denmark on October 1, 2009. EPA
Oprah Winfrey wears a navy silk Oscar de la Renta gown with a voluminous skirt to arrive at the 2010 Met Ball with designer Oscar de la Renta on May 3, 2010. EPA
Oprah Winfrey wears taupe Victoria Beckham to attend Maria Shriver’s Women’s Conference 2010 on October 26, 2010. EPA
Oprah Winfrey wears sparkling burgundy to arrive at the formal Artist's dinner held at the State Department with Stedman Graham on December 4, 2010. EPA
Oprah Winfrey wears a yellow top and beige capris to dance with Chef Curtis Stone on Hamilton Island, Australia on December 8, 2010. Getty Images
Oprah Winfrey wears a full orange dress during a taping of the 'Oprah Winfrey Show' at the Sydney Opera House on December 14, 2010 in Sydney, Australia. Getty Images
Oprah Winfrey wears emerald green Azzedine Alaia to arrive at the 19th Annual Critics' Choice Movie Awards in Santa Monica, California on January 16, 2014. EPA
Oprah Winfrey wears purple to arrive at the 20th Annual Screen Actors Guild Awards at the Shrine Auditorium in Los Angeles, California on January 18, 2014. EPA
Oprah Winfrey wears Stella McCartney to attend the 2014 EE British Academy Film Awards in London, England on February 16, 2014. EPA
Oprah Winfrey wears nude Vera Wang to attend the Vanity Fair Oscars After-Party following the 87th annual Academy Awards ceremony in Hollywood, California, USA on February 22, 2015. EPA
Oprah Winfrey wears a fitted sequinned orange gown on stage during her 'An Evening With Oprah' in Melbourne, Australia on tour on December 2, 2015. Getty Images
Oprah Winfrey wears a trained pink dress on stage during her 'An Evening With Oprah' tour in Sydney, Australia on December 12, 2015. Getty Images
Oprah Winfrey wears metallic brocade to attend the Tony Awards with Cynthia Erivo and Scott Sanders in New York on June 12, 2016. EPA
Oprah Winfrey wears Atelier Versace to attend the 75th annual Golden Globe Awards ceremony at the Beverly Hilton Hotel in Beverly Hills, California on January 7, 2018. EPA
Oprah Winfrey wears a black top, statement belt and floor-sweeping Brunello Cucinelli skirt to attend the European premiere of 'A Wrinkle in Time' in London, England on March 13, 2018. EPA
Oprah Winfrey wears blush pink Stella McCartney to arrive at St George's Chapel at Windsor Castle before the wedding of Prince Harry to Meghan Markle in Windsor, England on May 19, 2018. Getty Images
Oprah Winfrey wears navy to attend the Stella McCartney show as part of the Paris Fashion Week Womenswear Autumn / Winter 2019 on March 4, 2019 in Paris, France. Getty Images
Oprah Winfrey wears a white dress and white boots to arrive at the opening celebration of the Statue of Liberty Museum on Liberty Island on May 15, 2019. EPA
Oprah Winfrey wears a denim skirt with a white shirt and waistcoat to speak on stage during Oprah's 2020 Vision: Your Life in Focus Tour in Dallas, Texas on February 15, 2020. AFP
Oprah Winfrey wears a blush pink sweater and pleated skirt to interview Prince Harry and Meghan Markle for a CBS interview on March 7, 2021. Courtesy OSN
Oprah Winfrey wears a floral brooch to speak at a podium early in her career, during her time at WJZ, Baltimore, Maryland on January 20, 1978. Getty Images
Oprah Winfrey wears layered neutral knitwear and statement earrings to host 'AM Chicago' in 1984. Getty Images
Oprah Winfrey wears a white fringed gown and fur shawl to attend the 43rd Annual Golden Globe Awards on January 24, 1986 at the Beverly Hilton Hotel in Beverly Hills, California. Getty Images
Oprah Winfrey wears a white dress with gold detailing to attend 58th Annual Academy Awards with Akosua Busia on March 24, 1986 at the Dorothy Chandler Pavilion in Los Angeles, California. Getty Images
Oprah Winfrey wears a black fur coat to attend the premiere of 'Native Son' at the Apollo Theatre, New York City on December 8, 1986. Getty Images
Oprah Winfrey wears a black and gold sequinned dress to appear on 'Dolly' with Dolly Parton in 1987. Getty Images
Oprah Winfrey wears a black gown with sequinned detailing to attend the 59th Annual Academy Awards with Stedman Graham on March 30, 1987. Getty Images
Oprah Winfrey wears a red jacket over a black buttoned dress to attend the 14th Annual Daytime Emmy Awards on June 30, 1987. Getty Images
Oprah Winfrey wears a light brown fur coat to attend the 'Good Morning, Vietnam' premiere with Stedman Graham in Los Angeles, California on December 17, 1987. Getty Images
Oprah Winfrey wears a gold jacket with shoulder pads and jacquard skirt to attend the premiere of 'The Woman of Brewsters Place' at the Director's Guild Theatre in Hollywood, California on February 17, 1989. Getty Images
Opray Winfrey wears yellow and black tailoring to attend the 19th Annual Daytime Emmy Awards on June 23, 1992. Getty Images
Oprah Winfrey wears a pink floral corseted dress to attend the Daytime Emmy Awards on May 1, 1994. Getty Images
Oprah Winfrey wears a metallic purple two-piece to attend the 21st Annual Daytime Emmy Awards with Steadman Graham on May 25, 1994. Getty Images
Oprah Winfrey wears a dusty pink two-piece suit to attend the 'One Smart Lady' Ladies Home Journal Awards on November 11, 1994. Getty Images
Oprah Winfrey wears a brown silk gown with a taffeta train to attend the 67th Academy Awards in Los Angeles, California on March 27, 1995. FilmMagic
Oprah Winfrey wears a full light-blue skirt with a silver top to attend the 1995 Essence Awards with Stedman Graham at the Paramount Theatre in New York City on May 12, 1995. Getty Images
Oprah Winfrey wears an orange jacket during a segment on the 'The Oprah Winfrey Show' with Hillary Clinton in Chicago, Illinois on May 16, 1995. AFP
Oprah Winfrey, in head-to-toe red, attends The International Radio and TV Foundation Gold Medal award Dinner at the Waldorf Astoria Hotel in New York on March 21, 1996. Getty Images
Oprah Winfrey wears a navy gown with a gold shawl to attend the 68th Annual Academy Awards on March 25, 1996. Getty Images
Oprah Winfrey wears a black suit to attend the 'Before Women Had Wings' premiere in West Hollywood, California on October 20, 1997. Getty Images
Oprah Winfrey wears a red-and-black gown to attend 'Ebony Magazine' Celebrate the Dream: 50 Years of Ebony Magazine event on November 17, 1997. Getty Images
Oprah Winfrey wears a black dress with a metallic silver shawl to attend the 'Beloved' premiere on October 8, 1998. Getty Images
Oprah Winfrey wears a bronze two-piece to attend the 24th Annual People's Choice Awards with Stedman Graham on November 1, 1998. Getty Images
Oprah Winfrey wears an iridescent green and pink gown to attend the first anniversary party for 'O Magazine' in New York City on April 17, 2001. Getty Images
Oprah Winfrey wears a white shirt and trouser set on 'The Oprah Winfrey Show' with Stevie Wonder, John Travolta, Gayle King and Tina Turner in Chicago on January 29, 2004. EPA
Oprah Winfrey wears blue Gianfranco Ferre to attend the 76th Annual Academy Awards in Hollywood California on February 29, 2004. EPA
Oprah Winfrey wears a lilac dress with matching accessories to officiate at the Nobel Peace Prize Concert with actor Tom Cruise in Oslo, Norway on December 11, 2004. EPA
Oprah Winfrey wears a pink collared dress to meet pupils who have enrolled in her school in Henley-on-Klip, South Africa, on January 2, 2007. EPA
Oprah Winfrey wears co-ordinated shades of brown to attend a Barack Obama campaign rally in Iowa on December 8, 2007. EPA
Oprah Winfrey wears a white shirt with a pleated black skirt to attend a dinner in honour of Nelson Mandela's 90th birthday in London on June 25, 2008. Getty Images
Oprah Winfrey wears a green rain coat in Copenhagen, Denmark on September 20, 2009. EPA
Oprah Winfrey wears an orange shift dress to arrive at Amalienborg Castle, Denmark on October 1, 2009. EPA
Oprah Winfrey wears a navy silk Oscar de la Renta gown with a voluminous skirt to arrive at the 2010 Met Ball with designer Oscar de la Renta on May 3, 2010. EPA
Oprah Winfrey wears taupe Victoria Beckham to attend Maria Shriver’s Women’s Conference 2010 on October 26, 2010. EPA
Oprah Winfrey wears sparkling burgundy to arrive at the formal Artist's dinner held at the State Department with Stedman Graham on December 4, 2010. EPA
Oprah Winfrey wears a yellow top and beige capris to dance with Chef Curtis Stone on Hamilton Island, Australia on December 8, 2010. Getty Images
Oprah Winfrey wears a full orange dress during a taping of the 'Oprah Winfrey Show' at the Sydney Opera House on December 14, 2010 in Sydney, Australia. Getty Images
Oprah Winfrey wears emerald green Azzedine Alaia to arrive at the 19th Annual Critics' Choice Movie Awards in Santa Monica, California on January 16, 2014. EPA
Oprah Winfrey wears purple to arrive at the 20th Annual Screen Actors Guild Awards at the Shrine Auditorium in Los Angeles, California on January 18, 2014. EPA
Oprah Winfrey wears Stella McCartney to attend the 2014 EE British Academy Film Awards in London, England on February 16, 2014. EPA
Oprah Winfrey wears nude Vera Wang to attend the Vanity Fair Oscars After-Party following the 87th annual Academy Awards ceremony in Hollywood, California, USA on February 22, 2015. EPA
Oprah Winfrey wears a fitted sequinned orange gown on stage during her 'An Evening With Oprah' in Melbourne, Australia on tour on December 2, 2015. Getty Images
Oprah Winfrey wears a trained pink dress on stage during her 'An Evening With Oprah' tour in Sydney, Australia on December 12, 2015. Getty Images
Oprah Winfrey wears metallic brocade to attend the Tony Awards with Cynthia Erivo and Scott Sanders in New York on June 12, 2016. EPA
Oprah Winfrey wears Atelier Versace to attend the 75th annual Golden Globe Awards ceremony at the Beverly Hilton Hotel in Beverly Hills, California on January 7, 2018. EPA
Oprah Winfrey wears a black top, statement belt and floor-sweeping Brunello Cucinelli skirt to attend the European premiere of 'A Wrinkle in Time' in London, England on March 13, 2018. EPA
Oprah Winfrey wears blush pink Stella McCartney to arrive at St George's Chapel at Windsor Castle before the wedding of Prince Harry to Meghan Markle in Windsor, England on May 19, 2018. Getty Images
Oprah Winfrey wears navy to attend the Stella McCartney show as part of the Paris Fashion Week Womenswear Autumn / Winter 2019 on March 4, 2019 in Paris, France. Getty Images
Oprah Winfrey wears a white dress and white boots to arrive at the opening celebration of the Statue of Liberty Museum on Liberty Island on May 15, 2019. EPA
Oprah Winfrey wears a denim skirt with a white shirt and waistcoat to speak on stage during Oprah's 2020 Vision: Your Life in Focus Tour in Dallas, Texas on February 15, 2020. AFP
Oprah Winfrey wears a blush pink sweater and pleated skirt to interview Prince Harry and Meghan Markle for a CBS interview on March 7, 2021. Courtesy OSN