Oprah’s a-ha style moments

Post Staff Report

featured

Dec 18, 2013

1 of 9

Oprah kicks back in her Chicago office sporting cowboy boots with a sweater and oversize skirt. Although she’s savoring her success with the upcoming debut of “The Oprah Winfrey Show” in 1986, her personal style had yet to be discovered. Charlie Knoblock/AP

2 of 9

Having hit 212 pounds in 1987, Oprah whittles herself down to 145 with a fad liquid diet, then wriggles into size 10 Calvin Klein jeans to celebrate on the show. She later admits she regrets losing weight the fast and easy way: “I stayed at that weight for one day before the regaining began.” Charles Bennett/AP

3 of 9

In a blazer, big earrings and even bigger hair, Oprah tips the scales again and embraces the mannish power suits that she’ll continue to wear for years. (Two years later, she hits her highest-ever weight, reaching 237 pounds.) Jim Smeal/WireImage.com

4 of 9

Wow! Oprah debuts an updated pixie-style hairdo and a slimmed-down figure, showing it off in a corset dress by Valentino with a see-through skirt. “For a long time, I wanted to be buried in this [dress],” she has said. Jim Smeal/WireImage

5 of 9

For the launch of Oprah’s Book Club, Winfrey looks sleek, with her tamed tresses and fashionable boots (no more cowboy duds!). The huge sales increase for selected books becomes known as “the Oprah effect,” turning “White Oleander” and “The Story of Edgar Sawtelle,” among others, into runaway success stories. George Burns/Harpo, Inc.

6 of 9

Oprah’s softer side emerges with an abbreviated shag hairstyle (no more poufy bangs!) and a tailored, feminine suit in a tone of Champagne pink. We start to see less of her all-black ensembles. George Burns/Harpo Productions/AP

7 of 9

With her weight down to about 160 pounds, Oprah goes head to head with Halle Berry at the Academy Awards in a form-fitting gold gown by Vera Wang. Looks like it’s a tie! Chris Pizzello/AP

8 of 9

Channeling ’60s style with a half-up, half-down hairdo and fuchsia shift while filming her show in Central Park, Oprah reports her weight as 200 pounds. “I’m mad at myself,” she writes in O magazine, although she says health issues, including thyroid problems, contributed to the gain. One habit Oprah kicks for good, though, is suits. “I’d rather wear a lovely cashmere top or sweater instead,” she says. Marion Curtis/Startraksphoto.com

9 of 9

The Queen of Talk reigns in regal purple, the telltale red soles of her Louboutins peeking out. Off-air, though, she’s serious about comfort: As audience members can attest, she often walks out in bare feet, carrying her shoes before the cameras roll. Mario Anzuoni/Reuters

Fashion & Beauty

Comments

Powered by RoundtableBuilt on infrastructure designed for real-time media. Learn more at RTB.io.© Roundtable 2026. By using this site you agree to the Terms of Use and Privacy Policy