There’s never been a fashion chameleon quite like Madonna. Born Madonna Louise Ciccone, the singer rose to prominence in the ’80s by rocking oversized denim, teased hair, and piles of mostly diamond accessories. From there, she’s experimented with pointy lingerie, full goth glam, Rat Pack-inspired menswear, and lots and lots of corsets—she all but invited the “Cone Bra” during her 1990 Blonde Ambition Tour. And, while her onstage ensembles might be the most dramatic examples of her ever-shifting style, her red carpet looks have also reflected her penchant for pushing the boundaries of fashion. Below, a look back at some of Madonna’s most memorable red carpet moments.
1985: American Music Awards
In full rocker glam at the 1985 American Music Awards.
1987: American Music Awards
A bold red lip, coiffed pixie hair, and a dazzling gown quickly became Madonna’s go-to red carpet look during the early stages of her career.
1991: Cannes Film Festival
Madonna in her iconic cone bra at the 1991 Cannes Film Festival where she debuted her film In Bed With Madonna.
1991: Academy Awards
Madonna channeled another famous “M,” Marilyn Monroe, at the 1991 Oscars. She entered the venue hand-in-hand with Michael Jackson.
1995: MTV Video Music Awards
The pop legend was early to the exposed bra trend.
1995: American Music Awards
With Kenny “Babyface” Edmonds at the American Music Awards in 1995.
1998: Golden Globe Awards
Channeling dark, romantic glamour on the Golden Globes red carpet.
1997: MTV Video Music Awards
With her long-time manager Guy Oseary at the 1997 MTV Video Music Awards.
1998: Academy Awards
For the 1998 Academy Awards, Madonna slipped into a plunging satin gown that featured a tulle skirt.
2005: MTV Europe Music Awards
During her Confessions on a Dance Floor era, Madonna was all about dance-inspired outfits like this leotard she wore to the 2005 MTV Europe Music Awards.
2006: Grammy Awards
Madonna rocked a bedazzled mini dress and higher-than-high boots to the 2006 Grammys.
2008: Rock and Roll Hall of Fame Induction Ceremony
The singer paired a sheer a-line dress with leather shoes for her 2008 induction into the Rock and Roll Hall of Fame.
2008: Cannes Film Festival
In full sequined fringe at the 2008 Cannes Film Festival.
2009: Met Gala
At the 2009 Met Gala, Madonna channeled the “Model as Muse” theme with this ruffled mini dress, matching headpiece, and black racer boots.
2011: Met Gala
The bottle blonde looked ravishing at the 2011 Met Gala.
2012: W.E. Premiere
Madonna attended the UK premiere of W.E. in a caped LBD that she styled with bright red gloves.
2012: Golden Globe Awards
Madonna won big at the 2012 Golden Globes in this tiered, sequined confection.
2013: Met Gala
The Met Gala’s 2013 dress code, PUNK: Chaos to Couture, was tailored made for Madonna.
2014: Grammy Awards
In matching looks with her son David, Madonna was the ultimate cool mom at the 2014 Grammys.
2015: Grammy Awards
Madonna blinged-out a lingerie corset dress for her 2015 Grammys outfit.
2015: Met Gala
For the 2015 Met Gala, the singer went for a graphic Moschino dress that featured a one-shoulder cape.
2016: Met Gala
Madonna took her love of red carpet lingerie to extremes at the 2016 Met Gala.
2016: Billboard Women in Music
Madonna, at the 2016 Billboard Music Awards, suited up in a bold two-piece look.
2017: Met Gala
The singer went all out for the 2017 Met Gala in this camouflage gown.
2018: Met Gala
With a name like Madonna, it’s no wonder the singer was among the best dressed during the 2018 “Heavenly Bodies: Fashion & The Catholic Imagination” Met Gala.
2023: Grammy Awards
For the 2023 Grammy Awards, the icon cinched her waist with a chic, double-breasted coat. She rounded out her look with a braided hairdo.
2024: Deadpool & Wolverine Premiere
Madonna brought her oh-so stylish daughters, Stella and Estere, to the Deadpool & Wolverine premiere in 2024.
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