Oprah’s Most Memorable Looks

In 25 years of "The Oprah Winfrey Show," Oprah has had more looks than Derek Zoolander. Here's a look at some of her most memorable hairstyles and ensembles, '80s beauties included.

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Oprah Winfrey during The 76th Annual Academy Awards - Overhead View from The El Capitan Theatre at El Capitan Theatre in Hollywood, California, United States. (Photo by Lee Celano/WireImage)
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Talk show queen Oprah Winfrey signs off her top-rated program on Wednesday. In the 25 years of "The Oprah Winfrey Show," Oprah has had more looks than Derek Zoolander. Here's a look at some of her most memorable ensembles, '80s beauties included. Here, Oprah is stunning in a pale yellow Bradley Bayou gown at the 2002 Emmy Awards where she received the first-ever Bob Hope Humanitarian Award.
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Here's Oprah in 1986, the year her show premiered. Check out that paisley! See, the red lipstick, nails and necklaces pick up the taupe in her sweater.
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It's no secret Oprah has struggled with her weight. In what she called her "biggest, fattest mistake," she lost 67 pounds in four months with an all-liquid diet and dragged the equivalent weight in fat out on stage during a 1988 show. She said she saved the size 10 Calvin Kleins hoping to fit into them again. We like a bigger, healthier Oprah a lot more than we like those itty bitty jeans.
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Oprah wore gold Vera Wang to the 2005 Academy Awards in Hollywood. The neckline is nice, but is that fringe on the skirt's tiers? "This was one of my prettiest days, and I knew it," Winfrey said on her website.
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Oprah "OWNed" this elegant jade ensemble at the launch of the Oprah Winfrey Network earlier this year.
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EMPTY_CAPTION"O" boy. Oprah looks like a bedazzled peacock in this sparkly number she wore to the 1987 Academy Awards.
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Oprah in all her fringed glory at the 1986 Golden Globes, where she was up for (and lost) another award for best supporting actress. Think she was taking the "Queen of All Media" thing a little too seriously? "When I see old photos of myself, I really don't know what I was thinking," Oprah later said about the dress. "Somebody should have stopped me!"
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Ever the professional, Oprah's big on lapels, even on evening wear. Oprah rocked this tawny-hued dress at the Alvin Ailey American Dance Theater's 50th anniversary opening night gala in 2008. We love it almost as much as her long curly locks.
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Here's Oprah in an earth-toned, African-inspired print at the nominees luncheon for the 58th annual Academy Awards, in 1986. She was up for Best Actress in a Supporting Role for "The Color Purple." She lost out to Geraldine Page in "The Trip to Bountiful."
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Holding a Daytime Emmy Award after only being on the air for a year? Go, girl! Wearing this spangled monstrosity out in public? Bless her heart. We know it was 1987, but it wasn't the 4th of July!
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Oprah looking a little scary at the 1988 People's Choice Awards. "In 1988, my body got smaller -- but my hair doubled in size," Oprah said on oprah.com in 2008. We noticed ...
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Oprah looked like she was channeling Michael Jackson with the strong-shouldered, piped jacket she wore to the 1988 National Conference of Christians & Jews Humanitarian Dinner.
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Little known fact: Oprah occasionally moonlights as a living statue. Here's one of her early performances, at a 1989 screening of "The Women of Brewster Place," in Los Angeles.
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Knock, knock. Who's there? 1990! Here's Winfrey looking quintessentially 1990 in a lacy black gown, arriving at a ceremony devoted to her. Could that carnation be more perfect?
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Oprah picked up her second consecutive Emmy at the 1992 Daytime Emmy Awards at the Sheraton Hotel in New York City, but we have no awards -- or words -- for this bumblebee outfit.
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Oprah's looking fit and fabulous in a Valentino gown at the 1994 Daytime Emmy Awards at the Waldorf Astoria in New York City. "I loved it so much, I told Gayle that I wanted to be buried in it," Oprah later said of the dress on her website. We think she could probably find something better to wear for eternity. What's up with the exposed leotard below her waist?
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Now that's more like it! Oprah is a goddess in chocolate at the 67th Annual Academy Awards in 1995. See? Again with the lapels.
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Oprah said goodbye to her poofy '80s hair by the mid '90s, but the pastel taffeta ballgown skirt she wore to the 1995 Essence Awards at New York City's Paramount Theater made up for the lost volume. She's rocking some arm candy, too: longtime partner and mystery man Stedman Graham.
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We're happy she's happy, but that turtleneck, bleh! A casual weekend sweater met a ballgown skirt at an International Radio and Television Society Foundation ceremony in 1996.
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New York paparazzos spotted an all-black-everything Winfrey outside the Giorgio Armani Store in 1996. Are those harem pants?
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Here's Oprah in a beaded champagne-colored number at the 1996 Emmys. Check out those Michelle Obama arms! But bad posture, right? Pull back those shoulders!
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Now here's a power couple. Hillary Clinton and Oprah attend the 2000 Essence Awards at Radio City Music Hall in New York City. Oprah looks like a First Lady herself in this striking scarlet wrap gown.
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Oprah gets down with Tina Turner at the 2000 launch party for Oprah's new magazine "O." While pretty, Oprah's demure floral skirt is not exactly the fierce ensemble we'd have liked to see.
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It's red, it has a stand-up color, it's totally Oprah. America's favorite talk show host arrives at the Kennedy Center Honors Gala in December 2001.
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We think white is winning on Ms. Winfrey, pictured here with Halle Berry at the 2002 Carousel Of Hope Ball to benefit childhood diabetes.
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Oprah looking ethereal in a silvery Gianfranco Ferre gown at the 76th Academy Awards in 2004.
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Oprah went peachy and preppy for a 2004 Nobel Peace Prize press conference in Oslo.
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2005: Lady's in red at the Legends Ball in Santa Barbara. Love love love!
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That splash of purple is worn in honor of Oprah's passion project, "The Color Purple" at its Broadway premiere in 2005.
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Oprah looks regal in a breezy Gucci gown at the Oscars in 2007.
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PETA chose Oprah as their Person of the Year in 2008, but here she is wearing yards of leather at the 2007 premiere of the Denzel Washington flick "The Great Debaters."
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Looking demure in a pretty pink shirtdress at the opening ceremony of her $40 million Leadership Academy for Girls School outside Johannesburg, South Africa in 2007.
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Oprah flaunted her curves in a swingy gown in her favorite color at the 2008 Primetime Emmy Awards in Los Angeles.
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Oprah called the dress she wore in November 2009 when she announced the end of her show one of her all-time favorite, never-letting-them-go outfits. Her BFF Gayle King suggested she wear color, but she said she didn't want to detract from her message. The final episode of "The Oprah Winfrey Show" is set to air May 25.
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