HBD, Oprah! Here Are 10 Of Our Favorite Fashionable Moments From The Mogul

Oprah Winfrey is one of the most admirable African American media moguls of our time. She has built an empire that has inspired some of the most successful, financially-free people. Her ambition and accolades are to be studied and admired. At the age of 66, Oprah shows no signs of slowing down. Beyond her amazing and influential career lies her stylish wardrobe. Oprah is a fixture on the red carpet. She has given us decades of fashionable looks. We’ve seen her body transform from petite, to plus size, to standard size. It was her weight loss journey documented through Weight Watchers, that inspired others to follow in her footsteps. She was fly in 1995, but her style over the last 2 years have been a downright fabulous. Though her pieces are simple, they make memorable statements that will send you to the store shopping for, “that thing Oprah wore.” In honor of her 66th birthday, we’re checking out 10 of our favorite fashion moments from Oprah.

1. OPRAH AT THE 22ND DAYTIME EMMY AWARDS, 1995

Love 93.9 WKYS? Get more! Join the 93.9 WKYS Newsletter

This site is protected by reCAPTCHA and the Google Privacy Policy and Terms of Service apply.

Subscribe

We care about your data. See our privacy policy.

Oprah Winfrey posed with 2 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.

2. OPRAH AT THE 54TH DATYIME EMMY AWARDS, 2002

Oprah Winfrey attended The 54th Annual Primetime Emmy Awards in a gorgeous, yellow ball gown.

3. OPRAH AT STELLA MCCARTNEY'S PARIS FASHION WEEK SHOW, 2019

Oprah’s style has evolved from 1995 to 2020. Here she is at the Stella McCartney show during Paris Fashion Week clad in an all black, chic ensemble.

4. OPRAH AT AN APPLE PRODUCT LAUNCH, 2019

Oprah Winfrey 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.

5. OPRAH AT THE HOLLYWOOD REPORTER'S EMPOWERMENT IN ENTERTAINMENT EVENT, 2019

Oprah Winfrey attended The Hollywood Reporter’s Empowerment In Entertainment Event in a simple yellow dress, a slicked back ponytail, and a huge smile.

6. OPRAH AT THE 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.

7. OPRAH AT TYLER PERRY STUDIOS GRAND OPENING GALA, 2019

Oprah Winfrey and her longtime boo Stedman Graham looked elegant on the red carpet of Tyler Perry Studios Grand Opening Gala.

8. OPRAH AT HER 2020 VISION TOUR, 2020

Oprah Winfrey 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.

9. OPRAH AT HER 2020 VISION TOUR, 2020

On another stop of Oprah’s 2020 Vision: Your Life in Focus Tour, Oprah stunned in a casual khaki safari-inspired jumpsuit.

10. OPRAH AT THE 75TH ANNUAL GOLDEN GLOBE AWARDS, 2020

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