August 12th, 2026
To a young Oprah Winfrey, a pair of diamond earrings that caught her eye during a free concert represented much more than a fashion accessory. They became a goal — and a sparkling reminder of what success could look like. In a new interview for Glamour’s “Girlhood Firsts” video series, Winfrey recalled the moment Diana Ross, performing in a torrential downpour at her 1983 Central Park concert, inspired her to one day rock her own pair of 10-carat-total-weight diamond studs.
Winfrey was just 29 when she and 400,000 other fans watched Ross command the stage during her legendary free concert on Central Park’s Great Lawn. Rain poured down, but Ross kept performing for another 25 minutes until dangerous weather forced the concert to end.
“All you could see was diamond earrings glittering, and her mascara did not run,” Winfrey recalled.
The image made such an impression that Winfrey called Ross’ production company the following day. She wanted to know two things.
“I asked them what was the mascara and how many carats of diamonds [Ross’s earrings weighed], and they told me 10 carats, so I strived until I could get my first 10 carats,” Winfrey said.
(The mascara, by the way, was from Lancôme.)
Winfrey eventually bought her own 10-carat diamond studs, transforming the earrings into a personal milestone and symbol of achievement. But there was a hilarious twist. Years later, Ross told her that the earrings she had worn during the rainstorm actually totaled only 5 carats.
“I could’ve quit halfway through,” Winfrey joked.
The story offers a wonderful glimpse into how jewelry can represent aspiration as much as adornment. To Winfrey, those diamonds represented the level of accomplishment she wanted to achieve — and she pursued that goal with the same determination that eventually made her one of the world's most influential media figures.
Ross, meanwhile, was already a superstar when she performed in Central Park. After achieving legendary status as lead singer of The Supremes, she launched a hugely successful solo career that expanded into film and television. Her career now spans more than six decades, and she is among the best-selling recording artists in history, with more than 100 million records sold worldwide.
Winfrey’s own trajectory is equally remarkable. In 2007, Forbes ranked her the world’s most influential celebrity, while in 2026 she earned the #1 spot on Forbes’s list of the 250 Greatest Self-Made Americans. The publication estimates Winfrey's fortune at about $3.4 billion.
Credits: Oprah Winfrey photo (cropped) by vargas2040, Cropped by OsamaK, CC BY-SA 2.0, via Wikimedia Commons. Diana Ross photo (cropped) by Crisco 1492, CC BY-SA 4.0, via Wikimedia Commons.
Winfrey was just 29 when she and 400,000 other fans watched Ross command the stage during her legendary free concert on Central Park’s Great Lawn. Rain poured down, but Ross kept performing for another 25 minutes until dangerous weather forced the concert to end.
“All you could see was diamond earrings glittering, and her mascara did not run,” Winfrey recalled.
The image made such an impression that Winfrey called Ross’ production company the following day. She wanted to know two things.
“I asked them what was the mascara and how many carats of diamonds [Ross’s earrings weighed], and they told me 10 carats, so I strived until I could get my first 10 carats,” Winfrey said.
(The mascara, by the way, was from Lancôme.)
Winfrey eventually bought her own 10-carat diamond studs, transforming the earrings into a personal milestone and symbol of achievement. But there was a hilarious twist. Years later, Ross told her that the earrings she had worn during the rainstorm actually totaled only 5 carats.
“I could’ve quit halfway through,” Winfrey joked.
The story offers a wonderful glimpse into how jewelry can represent aspiration as much as adornment. To Winfrey, those diamonds represented the level of accomplishment she wanted to achieve — and she pursued that goal with the same determination that eventually made her one of the world's most influential media figures.
Ross, meanwhile, was already a superstar when she performed in Central Park. After achieving legendary status as lead singer of The Supremes, she launched a hugely successful solo career that expanded into film and television. Her career now spans more than six decades, and she is among the best-selling recording artists in history, with more than 100 million records sold worldwide.
Winfrey’s own trajectory is equally remarkable. In 2007, Forbes ranked her the world’s most influential celebrity, while in 2026 she earned the #1 spot on Forbes’s list of the 250 Greatest Self-Made Americans. The publication estimates Winfrey's fortune at about $3.4 billion.
Credits: Oprah Winfrey photo (cropped) by vargas2040, Cropped by OsamaK, CC BY-SA 2.0, via Wikimedia Commons. Diana Ross photo (cropped) by Crisco 1492, CC BY-SA 4.0, via Wikimedia Commons.
