Madonna's career has spanned an impressive five decades and is still going strong. She has never been afraid to reinvent herself or take a risk. The Queen of Pop moved from Bay City, Michigan, to New York City in the 1970s to pursue dance.
All of Madonna's reinventions and bold choices mean sometimes she nailed her fashion choices and other times not so much. Here are 10 outfits that were not her finest moments. You win some, you lose some.
The 2016 Met Gala
The annual Met Gala is the place to be seen. In 2016, the theme was "Manus x Machina: Fashion in an Age of Technology." Madonna wore a risky Givenchy ensemble that left little to the imagination. Her breasts and butt checks were on display although covered in strategic lace. Many took issue with this outfit but Madonna explained it was a politic statement on society's constraints on women.
'Blonde Ambition Tour'
The Blond Ambition World Tour was Madonna's third time around the world. She even stopped in Sweden and Spain for the first time. She was promoting her fourth studio album Like a Prayer, which was released in 1989. One of the sets had an old Hollywood glamour vibe and featured music from the 1990 film Dick Tracy. One of Madonna's costumes attempted to give Marilyn Monroe Gentlemen Prefer Blondes but wound up looking tacky.
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'Confessions on a Dance Floor'
Madonna donned a lot of spandex to promote her 10th studio album Confessions on a Dance Floor. There's got to be a better way. Here she is getting hot and sweaty performing at a weekly gay night called G-A-Y. This went down in 2005 at The Astoria in London.
A Velvet Hat
In the 1998 movie You Got Mail, Meg Ryan's character muses that almost all hats turn out to be mistakes. Perhaps this was in reference to Madonna's 1988 velvet one. She was spotted wearing it when leaving a Broadway theater. Let's hope this one got lost in a move or something.
More 'Confessions Tour'
Another fashion mishap occurred on the Confessions Tour. This equestrian look doesn't make the mark. Madonna should save it for trail rides, not the stage.
Jimmy Fallon Appearance
In 2022 Madonna appeared on The Tonight Show Starring Jimmy Fallon in a perplexing outfit. She wore a black corset top paired with blue baggy athletic pants. There were also heavy layered chain necklaces and lace gloves. Was she trying to be comfy? Was she going for the effortless look? Either way, it just didn't work.
2015 Grammy Awards
In 2015, Madonna donned a Givenchy Couture ensemble for the Grammy Awards. The pink and black corset dress was created by Italian designer Riccardo Tisci. The outfit may have been couture, but it felt more like a costume than a red carpet look. It was also cheeky, displaying her bum.
Eurovision
Yo ho, yo ho, this outfit makes Madonna look like a pirate queen in the worst way possible. It's bulky and there's an eye patch and tiara involved. This fashion disaster took place in Tel Aviv, Israel. Madonna was performing at the 64th annual Eurovision Song Contest.
'Madame X'
In 2019 Madonna released Madame X, her fourteenth studio album. This concept album was inspired by her experiences living as an expat in Portugal. In 2021 she celebrated her musical accomplishment at the Paradise Club and Theater at The Edition Hotel Times Square in New York City. She wore a white mini-skirt and black corset, which wasn't her best look. The weird headpiece and sunglasses didn't help the situation.
The '80s and '90s
Some of Madonna's questionable fashion choices are simply a product of the times. She embraced the '80s and '90s trends, but these just didn't age well. The big hair bows, excessive blue eye shadow, dark lipstick, and tank tops have had their moment in the sun. It is fun to revisit, though.
