The Boss: Nearly 80 Years Young, A Look Back at Diana Ross' Most Iconic Looks
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In what some have described as a surprising move, Yves Saint Laurent has chosen legendary singer Diana Ross as the new face of Saint Laurent by Anthony Vaccarello’s new spring 2024 campaign.
But if you really know about Diana Ross, then seeing her as the face as a part of an iconic fashion brand is par for the course seeing as how her fashions as the lead of The Supremes always took centerstage. So it’s in celebration of her new campaign that we thought it’d be fitting to take a look back at some of her most stylish looks.
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Picture it: Central Park, 1983. July 21, 1983 to be exact. Diana Ross dazzled in a sparkly pink jumpsuit in what would become one of her most iconic performances ever. Not only did she look like a million bucks, but this sparkly pink jumpsuit was the fashionable followup to an orange sparkly number she wore the day before at this concert that was unfortunately cut short due to crazy rain and thunderstorms.
IRTS Gold Medal Awards Ceremony, 1980
Diana Ross performs at the IRTS Gold Medal Award ceremony at the American Hotel.
This indigo number at the 1980 IRTS Gold Medal Awards is another look that solidified Diana’s signature look: sparkly, form-fitting dress and a dramatic cape. No matter what color, this fit will always be fly!
G.I.T. on Broadway, 1969
One of her last major performances as a part of The Supremes, Diana took the stage—and donned a variety of iconic looks to perform “G.I.T.” on Broadway in 1969. Also known as Diana Ross and The Supremes and The Temptations on Broadway, the television special produced by Motown Productions.
The Supremes, 1965
The Supremes (Cindy Birdsong, Diana Ross and Mary Wilson), wearing matching sequinned peach dresses with silver necklaces and earrings, during a live concert performance, circa 1965.
They may all be wearing the same dress but it was precisely because of The Supremes’ ahead of the curve fashion sense along with their silky smooth vocals, that propelled Ross as a fashion legend.
World AIDS Day, 2019
Diana Ross performs on stage during the 2019 World AIDS Day Concert “Keep the Promise” of AIDS Healthcare Foundation (AHF) at The Bomb Factory on November 29, 2019 in Dallas, Texas.
Once again, Queen Diana tapped into her tried and true “uniform,” this time opting for a saturated ruby red and sparkly cape. You know what they say, “if it ain’t broke—don’t fix it!”
“Endless Love” performance, 1987
Lionel Ritchie and Diana Ross team up to perform their hit “Endless Love” at a 1987 concert in Los Angeles, California.
We know “Endless Love” is a beloved song, and Lionel Ritchie was also a hearthrob at the time, but it’s Diana’s glam that takes the spotlight for us.
TV Land Awards, 2006
Diana Ross performs a medley of her famous hits including “Touch Me in the Morning,” “The Boss,” “Do You Know,” and “Ain’t No Mountain High Enough.”
There may not be a cape to accompany this look, but this sparkly jumpsuit Diana wore at the 2006 TV Land Awards is stellar all by itself.
TNT Christmas in Washington, 2012
Diana Ross performs onstage during TNT Christmas in Washington 2012 at National Building Museum on December 9, 2012 in Washington, DC.
What’s Christmas without Diana Ross?? And what’s Diana Ross without a regal looking gown to help usher in the season??
61st Grammy Awards
Diana Ross performs onstage during the 61st Annual GRAMMY Awards at Staples Center on February 10, 2019 in Los Angeles, California.
Name a better duo that Diana Ross and a stunning red dress? I’ll wait. The 61st Grammys stage was never the same.
Glastonbury Festival, 2022
Diana Ross performs on the Pyramid Stage during day five of Glastonbury Festival at Worthy Farm, Pilton on June 26, 2022 in Glastonbury, England.
Not only did Diana Ross come out on the Pyramid Stage at the 2022 Glastonbury Festival in beatifully dramamtic, icy white ensemble—but she turned the drama up a whole other notch by adding an elaborate, feathery head piece. THIS IS FASHION, folks.
American Music Awards, 2017
Diana Ross performs onstage during the 2017 American Music Awards at Microsoft Theater on November 19, 2017 in Los Angeles, California.
What did I tell you about her uniform? This time opting for a two-colored version, I’m never mad at this.
Muhammad Ali Celebrity Fight Night XIII, 2007
Diana Ross during Muhammad Ali’s Celebrity Fight Night XIII - Show at Marriot Desert Ridge Resort & Spa in Phoenix, Arizona, United States.
Folks may have shown up back in 2007 to see Muhammad Ali, but I can’t help but think the focus FULLY shifted once Diana took the stage in this billowy, white outfit.
Diana Ross in Concert, May 2010
Diana Ross performs at Radio City Music Hall on May 19, 2010 in New York City.
We don’t mean to sound hyperbolic, but out of all the looks, this by far has to be my favorite. Why? Because this is one of her bolder-colored uniform variants and one look we want to recreate IMMEDIATELY.
“Make Room for Grandaddy,” 1970
Diana Ross appearing on the Walt Disney Television via Getty Images series ‘Make Room for Granddaddy.’
The sleeves, the hair, the wispy eyelashes, the hair. There’s so much to admire about this look, and we are glad Diana had the confidence, swag, and allure to rock it.
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