Madonna Style Evolution: Her Most Iconic Transformations

Photography by Getty Images

We love you, Madonna!

By Maddison Glendinning

Date June 29, 2023

This article was originally published on August 16, 2019 and has been updated. 

The legend that is Madonna turns 61 today and to celebrate, we’re taking a look at some of her most memorable style transformations. One thing’s for sure: the evolution of Madonna’s style has been a wild ride.

The Marilyn Monroe moment in Material Girl

Madonna had only been on the scene for a few years when she recreated Marilyn Monroe’s famous Diamonds Are A Girl’s Best Friend look for her 1985 film clip for Material Girl. Giving an early hint to her unrivalled transformational abilities, the fur stole, fuchsia pink satin gown and drippings of diamonds made for a major moment.

The shaggy pixie crop in Papa Don’t Preach 

It might have been 1986 but Madonna’s bleach blonde pixie crop and thick eyebrows are the stuff Pinterest boards are filled with in 2019. Paired with a Breton stripe, oversized leather jacket and a black belted bustier jumpsuit, the controversial clip (many were enraged as they thought it promoted teen pregnancy) proved that a good crop (and great eyebrows) work in any situation.

The curls, cross and slip dress in Like A Prayer

Although the slip dress has become a street style must-have and mainstay in many wardrobes, Madonna was an early adopter of the look, sporting a body-con version of the item in her 1989 film clip for Like A Prayer. Paired with her mop of black curls and a stained lip, it’s one of the singer’s most iconic looks of all time.

The Gaultier cone bra

Speaking of iconic looks, a round-up of the musician’s style evolution wouldn’t be complete without a look at the Jean Paul Gaultier cone bra of 1990. Madonna unveiled the look on the first stop of her Blonde Ambition tour in Japan and no-one has stopped talking about it since. Interestingly, Gaultier admitted earlier this year in that he actually first designed the bra for a teddy bear he had growing up.

Photograph by Eugene Adebari/Shutterstock

The new era in Ray Of Light

In a huge sartorial turn, Madonna appeared in the music video for her 1998 hit Ray Of Light in a double denim look, soft beach waves and (because it was still the ’90s after all) a sequin belt. The release of the single coincided with her conversion to Kabbalah following the birth of her daughter, Lourdes, in 1996, and is one of her most pared-down to date.

The witchy Frozen era

That look didn’t last long however with Madonna crooning in the desert with long black hair in a flowing maxi dress for her 1998 hit Frozen. Serving up a desert witch vibe, the singer continued the look (albeit with a higher fashion twist) for her VH1 Fashion Awards appearance in the same year when she wore a corseted yellow gown by Olivier Theyskens, essentially putting the Belgian designer on the map.

Photo by Shutterstock

The gangster-cowboy hybrid in Music

Madonna ushered in the new millennium with yet another style shift, this time for her Music film clip. In it she rocked an all-white ensemble finished with an oversized fur jacket, multiple chains and rings and a bejewelled cowboy hat.

The ’70s vibe in Hung Up

Madonna proved age is only a number in 2005 sporting a low-cut fuchsia wrap-front top over a red high-leg bodysuit in her film clip for Music. The ’70s looked was completed with a curled, side-parted bob, 3/4 flesh-coloured tights and a purple sequinned belt.   

The Met Gala moment

Never one to shy away from a theme (see eight previous examples), Madonna is always one-to-watch on the annual Met Gala red carpet. Her first official appearance at the event was in 1997 but 2009’s outfit was the talk of the town. Strictly adhering to the theme ‘The Model As Muse: Embodying Fashion’, the Grammy Award-winning artist rocked a Louis Vuitton mini dress (designed by Marc Jacobs), thigh high black leather boots and custom couture bunny ears for the night. It made worst-dressed lists over the world but it kicked off a yearly countdown to see what she’d wear next.

Photograph by Matt Baron/BEI/Shutterstock

The ultimate transformation to Madame X

As with many of the aforementioned looks, the transformations were tied to album releases and Madonna’s style follows suit. Referring to herself as Madame X (which is also the name of her 14th album released back in June), the 61-year-old is rocking a bejewelled eyepatch on the reg paired with an array of edgy fashion looks from Versace, Prada, Miu Miu, Burberry, Fausto Puglisi and more. There’s elements from some of her previous iterations subtly woven into the new persona, though we’re certain this isn’t her last.

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