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The wildest Met Gala looks ever, from Naked Cher to ‘disastrous’ Madonna


The wildest Met Gala looks ever, from Naked Cher to ‘disastrous’ Madonna 


The Oscars may be fashion’s most high-profile event for celebrities, but the Met Gala is its three-ring circus.

“It used to be the high-fashion event of the year,” said historian Bronwyn Cosgrave, who hosts the “A Different Tweed” podcast. “Now it’s an elaborately themed costume ball.”

Founded in 1948 by fashion publicist Eleanor Lambert as a fundraiser for the Metropolitan Museum’s Costume Institute, the ball was taken over by former Vogue editor Diana Vreeland in 1972. Under the direction of Anna Wintour since 1995, the party has become New York’s version of the Wild West: Anything goes, but the louder and crazier, the better.

On Monday, the gala returns for the first time since 2019. The theme, “In America: A Lexicon of Fashion,” is broad, so it’s hard to predict if celebs (among the reported attendees are Jennifer Lopez, Billie Eilish, Naomi Osaka and Rihanna) will be pandemic-subdued — or use lockdown fatigue as a reason to live it up.

Melissa Rivers, former co-host of “Fashion Police,” hopes for the latter: “The Met Gala reminds us that fashion should be fun! It’s become a spectacle in the best possible sense.” Here, Cosgrave and Rivers look back on some of the ball’s most outrageous looks of all time — and we rank celebs by the Anna Meter (named for Wintour, of course).

1 Anna: You’ll never make the cover of Vogue in that. 2 Annas: Worth lowering the sun-glasses for a second look. 3 Annas: So bonkers it’s on the verge of brilliant. 4 Annas: Absolutely iconic.

Cher, 1974

3 out of 4 Annas.
3 out of 4 Annas.
Ron Galella via Getty Images

THEME: “Romantic and Glamorous Hollywood Costume”
Wearing a sheer and feathered gown by her favorite designer, Bob Mackie, Cher pioneered the “naked dress” style that would later become a Met Gala staple — worn by everyone from Beyoncé to Jennifer Lopez to, repeatedly, Kim Kardashian.

BC: “With that Bob Mackie dress, Cher put the Met Gala on the
map. People were shocked, but they knew she was paying respect to what Mrs. Vreeland loved: costume. She looks almost like a creature from another planet.”

MR: “Bob Mackie really piloted “the naked look,” but everyone else gets credit for it. Kim Kardashian was really clear she knew it was a Cher type moment when she wore a similar dress in 2015. Cher was the most outrageous woman on the red carpet for years. She understood that fashion is part of entertainment — she got that before [anyone else] did!”


2 out of 4 Annas.
2 out of 4 Annas.
WireImage; AFP/Getty Images

THEME: Manus x Machina: Fashion in an Age of Technology
Bare Madonna was nothing new, but it still felt shocking on the Met red carpet. But the singer claimed her Givenchy by Riccardo Tisci look was a political statement: “The fact that people actually believe a woman is not allowed to express her sexuality and be adventurous past a certain age is proof that we still live in an age-ist and sexist society,” she once said.

BC: “This is a disaster, I’m sorry — and I love Madonna. This was her pushing it just too far. It’s just not doing anything for her. The jewelry doesn’t work either. There’s a jewel at her chest, on her forehead. She could have lost a few. The black nails and red lipstick don’t work either.”

MR: “I have a love/hate relationship with Madonna’s fashion sense. This feels like she’s dying for attention, in all the wrong ways. I love the fact that her body’s still insane, and she works her ass off on it. But this would have made more of a statement if the boobs and butt were covered.”

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