Oprah Winfrey's Most Fashionable Looks

Oprah Winfrey is one of the most admirable African American media moguls of our time. While her ambition and accolades are to be studied and admired, we can take note on the years of fashionable looks she’s served us as well. We’ve counted down her 15 most fashionable moments:

1. 22ND DAYTIME EMMY AWARDS (1995)

Oprah posed with two awards at the 22nd Daytime Emmy Awards in a simple, powder pink gown. By 1995, she had established herself as a successful actress and talk show host.

The media mogul paved the way for many actresses, philanthropists, talk show hosts, and many more. In addition to making professional strides, she’s become a key person to watch during every major red carpet event.

2. 75TH ANNUAL GOLDEN GLOBE AWARDS (2020)

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Oprah posed with the Cecil B. DeMille Award during The 75th Annual Golden Globe Awards in a form-fitting black gown.

With her glasses and award in tow, the media mogul looked absolutely stunning. 

3. PREMIERE OF OWN'S "DAVID MAKES MAN" (2019)

Is anyone else obsessed with the way Oprah matched her glasses with her dress? Just me? Oprah attended the premiere of OWN’s “David Makes Man” in a simple white dress, gorgeous curls, and chic glasses.

Oprah clearly has a drawer full of diverse, fun frames. I love that each outfit she wears features a new set of glasses that somehow tie into her outfit — accessorizing at its finest.

4. Oprah's 2020 VISION TOUR (2020)

Oprah spoke during the WW (Weight Watchers Reimagined) & Oprah’s 2020 Vision: Your Life In Focus Tour in a stylish, khaki duster, paired with white slacks.

Everything about this ensemble was chic and timeless, particularly her white Stella McCartney platform lace-up brogues.

5. Oprah's The Life You Want Weekend – Day 1 (2014)

Oprah wore a stunning purple gown  at the Oprah’s The Life You Want Weekend – Day 1.

6. APPLE PRODUCT LAUNCH (2019)

Oprah gave a chic spin on the term “business casual” during an Apple product launch event at the Steve Jobs Theater. She wore black slacks, a white high-low blouse, and a black tie.

As the media mogul gets older, she takes great interest in finding fun yet comfortable clothing that speak to her personal style. This black and white ensemble fits her personality perfectly!

7. Premiere of Disney's "A Wrinkle In Time" (2018)

Oprah served grown woman vibes wearing a deep cut cobalt blue dress to the premiere of Disney’s “A Wrinkle In Time.”

8. Taping of "Queen Sugar After-Show" (2017)

Oprah looked studious with a slick ponytail, glasses, black tie and gray vest for the taping of “Queen Sugar After-Show” at OWN. 

9. OWN's 2011 TCA Winter Press Tour Cocktail Party (2011)

Oprah opted for an emerald pants ensemble with a matching coat for OWN’s2011 TCA Winter Press Tour Cocktail Party.

10. EE British Academy Film Awards (2014)

Oprah wore a burgundy gown with lace details to the 2014 EE British Academy Film Awards in London, England. 

11. 70th Annual Tony Awards (2016)

Oprah wore a metallic teal and cobalt gray quarter-length dress as she spoke on the Broadway musical The Color Purple during the 70th Annual Tony Awards. 

12. Prince Harry & Meghan Markle's Wedding (2018)

It’s the hat for us! Oprah arrived at St George’s Chapel at Windsor Castle before the wedding of Prince Harry to Meghan Markle in Windsor, England looking stunning.

13. An Evening With Oprah (2015)

Oprah wore a stunning pink high-low dress on stage during her ‘An Evening With Oprah’ tour at Allphones Arena in Sydney, Australia. 

14. 5th Annual Directors Guild of America Honors (2004)

Oprah posed backstage at the 5th Annual Directors Guild of America Honors. The media mogul wore a beige knee-length dress with a silk wrap belt that perfectly cinched her waist.

15. 87th Annual Academy Awards (2015)

Oprah attended the 87th Annual Academy Awards at Hollywood & Highland Center wearing a soft flowing quarter-lenght sleeve gown.