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Moments In Fashion & Beauty: Oprah Winfrey On Vogue Magazine Covers: 1998 & 2018

TV MOGUL OPRAH WINFREY never considered herself a beauty, but when the team from Vogue magazine had finished making her over for their covers, she was shocked at the photographs. By Ben Arogundade. Mar.16.2021.

OPRAH'S VOGUE MOMENT: Television star Oprah Winfrey graces the cover of the October 1998 edition of American Vogue, (left), and the August 2018 edition of British Vogue. There was a 20-year gap between covers. Photographs by Steven Meisel/Mert Alas and Marcus Piggott.

IT WASN'T UNTIL SUPERMODEL Donyale Luna in 1966 that Vogue magazine promoted its first African American cover model. Since then, on the rare occasions when black faces have featured on the cover of the world's premier fashion magazine, they have mostly been models. Television celebrity Oprah Winfrey became first African American screen star to break the mould when she featured on the cover of the October 1998 edition of American Vogue. The issue coincided with her acting debut in the hit movie Beloved, based on Toni Morrison’s Pulitzer Prize-winning novel about a former African American slave visited by the ghost of her dead daughter.


OPRAH TOO BIG FOR VOGUE MAGAZINE

The historic cover attracted extra attention, as it was revealed that Vogue editor Anna Wintour suggested that the talk show queen — who has struggled with her weight for years — lose 20 pounds in preparation for the cover shoot. “It was a very gentle suggestion,” Wintour recalled. “I went to Chicago to visit Oprah, and I suggested that it might be an idea that she lose a little bit of weight. I said simply that you might feel more comfortable. She was a trouper!”


Winfrey packed herself off to her retreat in Telluride, Colorado, together with her personal trainer and cook, where she embarked upon a rigorous diet and exercise program to drop the crucial pounds in preparation for the Vogue photo shoot with fashion photographer Steven Meisel.


OPRAH'S TEARS AT PHOTOS

For the naturally curvy Winfrey, who has campaigned tirelessly for American women not to succumb to society’s pressure to be thin, her decision seemed like a U-turn. But there was a powerful psychological driver behind her determination to slim down for the Vogue cover. As a teenager Oprah had competed in a number of African American beauty pageants, but had never considered herself attractive enough for fashion’s premier title. “Vogue is the big house!” she exclaimed. “Didn’t think I’d be sittin’ at that table!”


OPRAH'S MAGAZINE MOMENT

On the day of the magazine cover shoot with Meisel, when he handed her the first Polaroid’s of herself in full hair and make-up and costume, she burst into tears. “I was overwhelmed with emotion,” Winfrey recalled. “I was having an I-used-to-weigh-237 pounds-and-now-I’m-shooting-the-cover-of-Vogue moment.” The resulting October 1998 cover, featuring the face, and trimmed down figure, of the most famous black woman in the world, flew off the newsstands when it finally went on sale. “It was one of our most successful covers ever,” Wintour told 60 Minutes.


OPRAH ON VOGUE - AGAIN

Oprah may have been forgiven for thinking that she’d had her moment of Vogue cover glory, but then, 20 years later, she was asked to feature on a Vogue cover again — this time for the UK edition, edited by Edward Enninful, and featuring Winfrey in a bespoke Stella McCartney gown. On this occasion there were no surprised tears of joy about how she appeared in the photographs. While promoting the shoot on social media, Winfrey said the magazine staff made her feel like an "Empress for a day."

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ABOUT ME

Hi there. I am a London-based author and publisher, specialising in fiction, non-fiction and online journalism. Discover more about me and my latest projects, at Ben Arogundade bio.

OPRAH’S UK VOGUE COVER INTERVIEW 2018

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