Oprah’s Best Outfits Through the Years, Photos

From elegant dresses to sharp trousers and blouses, discover Oprah’s best looks over the years.

2002

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Oprah Winfrey attends the Vanity Fair Oscar Party at Mortons March 24, 2002 in West Hollywood.
76th Annual Academy Awards – Arrivals

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Oprah Winfrey attends the 76th Annual Academy Awards at the Kodak Theater on Feb. 29, 2004, in Hollywood.
2008

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Oprah Winfrey arrives to the 17th Annual Women In Entertainment Power 100 Breakfast on Dec 5, 2008, at the Beverly Hills Hotel in Los Angeles.
2010

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Oprah wears a black silk blazer, black trousers and peep-toe pumps with a metallic handbag in March 2010.
2013

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Oprah wears a purple sweater, blue jeans and metallic thong sandals in October 2013.
2017

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Oprah wears a yellow and black hoodie, black trousers and black leather ankle boots while attending the “Released” premiere at the Tribeca TV Festival in September 2017.
2018

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Oprah wears a striped vest, jeans and navy sneakers at Lucques Californian Restaurant in West Hollywood in February 2018.
2018

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Oprah wears a navy dress with sheer panels and sequined pointed-toe pumps at the “A Wrinkle In Time” premeire at the El Capitan Theatre in Los Angeles, California in February 2018.
2018

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Oprah wears a pale pink dress and Mary Jame pumps with a wide hat and Gabriela Hearst handbag at the Royal Wedding of Prince Harry to Meghan Markle in May 2018.
2018

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Oprah wears a striped blouse, white pants, a black and white handbag and white slip-on sneakers in Portofino, Italy in August 2018.
2019

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Oprah wears a navy knit sweater, maxi dress and black leather ankle boots while leaving the Stella McCartney Fall 2019 show during Paris Fashion Week in March 2019.
2019

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Oprah wears a printed coat, white silk trousers and black ankle boots while arriving at the Women In The World Summit in New York City in April 2019.
2019

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Oprah wears a white blouse and maxi skirt with matching Cuban-heel boots and a top-handle bag to the Statue Of Liberty Museum opening in May 2019.
2021

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Interviewing Prince Harry and Meghan Markle, Oprah wears a collared shirt, pink sweater and skirt with brown leather boots.
2022

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Oprah wearing a pinstriped suit with cap toe pumps at the Toronto International Film Festival on Sept. 11, 2022
2023

Image Credit: Michael Buckner for Variety

Oprah wears a sparkling sequined purple gown from Dolce & Gabbana at the Academy Museum Gala in Los Angeles on Dec. 3, 2023.
2023

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Oprah Winfrey wearing a satiny purple ensemble with a crystal embellished jacket and sparkling lavender sneakers outside the Empire State Building on Dec. 12, 2023 in New York City.
2024

Image Credit: Alberto Rodriguez/Golden Globes 2024

Oprah wears a purple Louis Vuitton gown with matching pumps at the Golden Globes in Los Angeles on Jan. 7, 2024.
2024

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Oprah wearing a purple Christian Siriano suit with purple pumps at the Democratic National Convention on Aug. 21, 2024.
2024

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Oprah wearing a Louis Vuitton striped track suit with metallic and canvas sneakers in Manhattan on Aug. 23, 2024.
2024

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Oprah Winfrey is seen on “Good Morning America” on Sept 10, 2024, in New York.
2024

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Oprah Winfrey is seen arriving at “Jimmy Kimmel Live” on Sept. 17, 2024, in Los Angeles.
2024

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Democratic presidential nominee, U.S. Vice President Kamala Harris (R) speaks alongside Oprah Winfrey during the closing rally of her campaign at the base of the iconic “Rocky Steps” at the Philadelphia Museum of Art on Nov. 05, 2024, in Philadelphia, Pennsylvania. With one day to go until election day, Vice President Kamala Harris is campaigning across Pennsylvania. (Photo by Kent Nishimura/Getty Images)