25 years of Oprah: We look back at the queen of daytime’s top ten fashion moments

After 25 years on air, today marks the last The Oprah Show EVER! While we’re all going to be busy shedding a tear (or two, or three) as we watch the Queen of Daytime scream her last scream and say her last goodbye, let’s take a moment to look back at some of Oprah Winfrey’s greatest fashion moments over the years. The inimitable talkshow host-cum-media mogul has gone through many style evolutions since her first show in 1986, but her great love and knowledge of fashion has stayed constant. Through moments of sniffles, take a look at our picks for Winfrey’s best fashion-savvy moments and be sure to tune in at 4pm EST for her final farewell episode. Kleenex at the ready!

1. On November 15, 1988, Winfrey stripped off an oversized coat to show off her 145-pound figure in Calvin Klein jeans after losing 67 pounds. In her grip was a wagon containing—you guessed it—67 pounds of fat that she no longer had to carry around.

2. The October 1998 issue of American Vogue was graced by Winfrey in a sleek and sexy strapless number. While the term “little black dress,” comes to mind, the powerful cover screams more than just LBD. Despite the controversy over Anna Wintour rumoured instruction to lose 20 pounds, the mogul looked breathtaking. It’s safe to assume that there were a lot of copies sold that month!

4. Many musicians have made appearances on The Oprah Show over the past 25 years, but perhaps one of the most memorable moments was when Winfrey and Tina Turner rocked her stage in 1997. Dancing beside one another, the two looked almost like twins but Winfrey had strategically planned her leather pants so as to not compete with the legendary singer’s equally legendary legs.

5. Rocking a casual but classy jean jacket and diamond necklace, Winfrey got her ears pierced on-air in September 2005. Worth all of the squirming and shrieking, she ended the show with two beautiful jeweled editions to her ear lobes.

6. In November 2005, Winfrey launched what she called “The Bra Revolution” to increase the availability of sexy plus size lingerie in America. With the help of recently plus sized actress, Kirstie Alley, she broadcasted how to find a bra that really fits. After this female revolution, Winfrey—and her lingerie—had a perfect hold of her audience.

7. In September 2009, Winfrey took her entire set back in time to the 1960s with January Jones and Jon Hamm for a special episode focused on Mad Men. Complete with Winfrey donning a Janie Bryant-made ’60s dress, the blast from the past quenched the audience’s perpetual thirst for nostalgia ever since the show hit air.

8. On the cover of O Magazine’s holiday issue in November 2009, Winfrey appeared alongside Ellen Degeneres in a drop dead red Prabal Gurung gown. The mogul showed real fashion savvy by donning the up and comer at the peak of his rise.

9. In February 2011, it would have been easy to mistake Winfrey’s set for an ’90s runway. Hosting an all-star lineup of Christie Brinkley, Beverly Johnson, Stephanie Seymour and Cheryl Tiegs, she talked all things ’90s supermodel from body issues to career moments.

10. Earlier this month, Oprah interviewed Ralph Lauren at his 17 000 acre ranch in Telluride, Colorado. She’s the first person to get broadcast an inside look of the designer’s home, and she just might be the last.

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