The Boss: Nearly 80 Years Young, A Look Back at Diana Ross' Most Iconic Looks

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.

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!

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.

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.

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!”

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.

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.

What’s Christmas without Diana Ross?? And what’s Diana Ross without a regal looking gown to help usher in the season??

Name a better duo that Diana Ross and a stunning red dress? I’ll wait. The 61st Grammys stage was never the same.

Not only did Diana Ross come out on the Pyramid Stage at the 2022 Glastonbury Festival in beautifully dramatic, icy white ensemble—but she turned the drama up a whole other notch by adding an elaborate, feathery head piece. THIS IS FASHION, folks.

What did I tell you about her uniform? This time opting for a two-colored version, I’m never mad at this.

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.

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.

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.