In her first months on air for her local show AM Chicago, Oprah interviewed Barbara Walters. With her hair cut short and clad in a cream power-blazer, white stockings, and big plastic earrings, Oprah showed off several 1980s trends. When the clip aired during Oprah's visit to The View in February, Walters joked to her: "I am totally responsible for your career, Oprah."
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In a moment of triumph in 1988, Oprah unveiled her 67-pound weight loss by wheeling a wagon of fat onto the stage. She finally was able to fit back into her smallest pair of Calvin Klein jeans, which she wore with a form-fitting black turtleneck. The weight loss was the result of an extreme diet called Optifast, which consisted of fasting and eating supplements. "What I didn't know is that my metabolism was shot," Winfrey now says. "Seventeen years after that show, I know a whole lot better."
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When Tina Turner came on the show in 1997, it was necessary for Oprah to pay homage in style: She donned a black leather jumpsuit to sing alongside the music icon. She says she chose the outfit so she didn't have to show her legs. "You cannot have your legs being compared with Tina Turner's!"
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At the height of 1990s "minimalism," Oprah showed off her fit physique in a slinky dress at the People's Choice Awards, where she picked up a trophy for Favorite Female Performer in a TV Series.
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An interview with Nelson Mandela in 2000 inspired Oprah to build a leadership academy for girls in South Africa. Mandela joined her to break ground on the Johannesburg facility, which opened its doors in 2007.
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For her "Favorite Things" episode in 2004, Oprah wore a brown and green leather skirt by Hermes. The mogul, who rarely goes shopping, reportedly picked this skirt out herself. The next year, however, Oprah wasn't as fond of the French fashion house: She was turned away from Hermes' Paris store when she arrived at closing time to buy a watch for her friend Tina Turner. She wrote immediately to the president of the company, informing him that she would never shop there again. He issued a public apology, "Hermes regrets not having been able to accommodate Ms. Winfrey and her team and to provide her with the service and care that Hermes strives to provide to each and every one of its customers worldwide." Winfrey forgave him and invited him on her show soon after.
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When the show's 19th season kicked off with a "Favorite Things" episode in 2005, Oprah sent a strong message. She appeared in a bright red Celine skirt-suit, which matched the red ribbon on the key chains she handed to each member of the studio audience—when she gave them keys to their own Pontiac. "Gayle and the producer came to us right before the show started and said, 'We don't think she should wear that,'" Kelly Hurliman, Oprah's stylist, remembers in this month's issue of O, The Oprah Magazine.. "'It's not fun enough.'" But Oprah said, 'I love this suit, it's the right look, I'm not changing.'"
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Oprah glowed on the red carpet at the Academy Awards in 2005, the year Jaime Foxx took home the Best Actor award for his performance in Ray. In a golden Vera Wang couture dress, Oprah looked positively statuesque. "This was one of my prettiest days—and I knew it," she later said of her dress.
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Oprah's show on June 21, 2005, will never be remembered for its subtlety. Tom Cruise, her guest for the episode, made talk-show history when he jumped on her couch to proclaim his love for Katie Holmes. But Oprah's outfit on that day was also memorable: an understated pink skirt and blush-colored sweater, which she paired with tear-drop earrings and pink heels. "I've never seen you like this!" she yelled as Cruise bounced around the stage.
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After decades of memorable jeans and power suits, Oprah's style became defined by understated classics by 2006. She wore a brown Lanvin skirt with a Dolce & Gabbana belt and a Valentino sweater on her show in 2006. According to Adam Glassman, creative director of O, Lanvin is one of Oprah's favorite designers.
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After Senator Barack Obama first came on the show in October 2006, Winfrey urged him to run for president. In a gray flannel dress by Alexander McQueen, Oprah questioned Obama about his plans for the future.
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Oprah stayed mum on her political preference for so long that when she finally did, it became a major moment in American political history. Winfrey first appeared alongside the Obamas in the fall of 2007, when she hosted a fundraiser on his behalf. She then attended four campaign appearances with him that December. Though pundits at the time thought it wouldn't mean much for the campaign, two economists later estimated that Oprah's endorsement translated to more than a million votes for Obama—and made the difference in his winning the Democratic nomination.
The 1960s revival peaked in 2009 with the hit show Mad Men. So when Oprah had stars January Jones and Jon Hamm on the show that September, she transformed her studio into the world of the show's advertising firm, Sterling Cooper. And Oprah certainly looked the part: Mad Men's costume designer, Janie Bryant, designed a pink silk dress for her to wear.
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In May 2010, Oprah co-hosted the Costume Institute Gala Benefit at the Metropolitan Museum of Art in New York, which celebrated the opening of the exhibition American Woman: Fashioning a National Identity. Winfrey wore a glittering navy blue dress by Oscar de la Renta (crafted by four dressmakers over 250 hours), and she appeared on the red carpet with the designer.
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Oprah channeled high glamour at the Academy Awards in 2011, where she presented the award for Best Documentary in a glittering Zac Posen dress.
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For her big farewell, "Surprise Oprah! A Farewell Spectacular," which will air on Monday and Tuesday ( Wednesday's finale will be a surprise, Oprah was joined on stage by some of her closest friends, including Tom Cruise, Stevie Wonder, and Aretha Franklin. She wore a custom-made L'Wren Scott purple crepe gown with handmade turquoise and black floral embroidery. On Tuesday, it was announced that Scott will create a shorter version of the dress, which will go on sale at Barneys New York next week.
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