Winfrey described an iconic moment in Ross’ career and how it inspired her
Credit: Sonia Moskowitz/IMAGES/Getty; Michael Loccisano/Getty
NEED TO KNOW
- Oprah Winfrey revealed to Glamour how Diana Ross inspired her to buy her first pair of diamond earrings
- In an episode of the outlet’s “Girlhood Firsts” series, the former talk show host turned podcaster looked back on Ross’ free concert in Central Park, which took place in 1983
- Ross performed at the landmark’s Great Lawn for nearly half an hour before torrential rain halted the concert
Oprah Winfrey has Diana Ross to thank for one of her most memorable jewelry purchases.
The Emmy-winning talk show host can distinctly remember one of the moments when the “I’m Coming Out” singer took her breath away decades ago, and she reflected on the fond memory in a segment for Glamour’s “Girlhood Firsts” series.
In a clip shared on Wednesday, Aug. 5, Winfrey, 72, was asked about the first time she felt “represented in media” to which she recalled Ross’ free performance at Central Park’s Great Lawn in 1983. The concert, Winfrey recalled, was when Ross, now 82, became her “inspiration and aspiration” for her “first diamond stud earrings.”
Credit: Joe McNally/Getty
“Because if you all remember… There she is. There is a storm that came in Central Park, and she kept singing. It was like pouring rain,” Winfrey recalled of the performance, which according to a 1983 article from The New York Times lasted 25 minutes before weather disrupted it.
Winfrey added, “All you could see was diamond earrings glittering, and her mascara did not run.”
Winfrey was so in awe that she called up Ross’ production company the next day to get details on the superstar’s eye makeup (which was by Lancôme) and jewelry. “I asked them what was the mascara and how many carats of diamonds [Ross’ earrings weighed], and they told me 10 carats, so I strived until I could get my first 10 carats.”
However, Winfrey later discovered that Ross’ earrings were only 5 carats, to which she joked, “I could’ve quit halfway through.”
Credit: Sonia Moskowitz/Getty
Elsewhere in the clip, Winfrey called out other moments that empowered her during her childhood. Those included Sidney Poitier becoming the first Black man to win an Oscar in 1964 and The Supremes appearing on The Ed Sullivan Show.
Of the latter, Winfrey said, “We had never seen anything like that. We had not seen Black women look like that, we had not seen Black women be that glamorous, we had not seen Black women talk like that. It was incredible.”
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Ross’ sense of style remains iconic, and one of her most recent jaw-dropping moments occurred at the 2025 Met Gala. She arrived at fashion’s biggest night in a grand ensemble that she designed herself with family and her 1975 movie Mahogany in mind.
Not only did it feature a glittering gown, but it was accessorized with a ultra wide-brimmed hat and an 18-foot train.
Ross told La La Anthony during the Vogue livestream, “If you ever had pictures of the inside of the train, it has the names of all my children, and my eight grandchildren. Everybody’s name is embroidered in that.”
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