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).


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!”


Madonna, 2016

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.”


Rihanna, 2017

4 out of 4 Annas.
4 out of 4 Annas.
Neilson Barnard/Getty Images

THEME: “Rei Kawakubo/Comme des Garçons: Art of the In-Between”
Rihanna has been fearless at the Met Gala over the past several years. In 2017, she donned a Comme des Garcons by Rei Kawakuba frock that looked like an art installation and was anything but body-conscious. For 2015’s “China: Through the Looking Glass”  theme, she shut down — or smothered? — the red carpet in a couture gown by designer Guo Pei that took two years to create and included a 16-foot train.

BC: “This 2017 petal look allows her to be outrageous, but she’s so beautiful, she still looks like a flower. Rihanna’s face never gets distracted from by a big look. You notice the person as much as this outrageous costume.”

MR: “How could Rihanna ever top that magnificent 2015 Chinese couture look?
No one will ever top it. Not even Rihanna. But my question is, how do you check that
coat? You simply can’t eat dinner in that. Unless you eat standing.”


Jared Leto, 2019

2 out of 4 Annas.
2 out of 4 Annas.
Getty Images; Wireimage

THEME: “Camp: Notes on Fashion”
Jaws dropped when Leto showed up carrying what appeared to be a clone of his own head — then proceeded to goofily mug with it on the red carpet. But fashion insiders thought it was old hat: Gucci’s Alessandro Michele had sent models toting their “heads” down the runway the previous year.

MR: “I understand the theme was camp, but this wasn’t camp. It was creepy.”

BC: “Jared Leto kickstarted outrageous dressing for male actors. Prior to him, the red carpet uniform was a black tux. Jared actually looks great in the dress. Gucci that season had these head clutches in that collection, which is to me why it doesn’t work —we’d seen it before. Anyone in fashion would know that look’s straight from the runway.”


Liv Tyler and Stella McCartney, 1999

3 out of 4 Annas.
3 out of 4 Annas.
Getty Images

THEME: “Rock Style”
Some people thought it was bratty when Tyler (the daughter of Aerosmith frontman Steven Tyler) and McCartney (one of Paul McCartney’s five kids) turned up in homemade-looking T-shirts that read “Rock Royalty.” But there was more to McCartney’s design concept.

BC: “This really works because they’re young. The moment you put a ballgown and
dowager jewelry on young women, it backfires. This punk look goes back to Vivienne Westwood [when the designer worked with bands like the Sex Pistols and Bow Wow Wow]. It punk and it cuts through the frivolity to make a statement. And it’s the moment the couture T-shirt craze was born.”

MR: “This was poking fun at the whole concept of Met Ball. But you have to be
them — real rock royalty — to get away with it. If I could still wear Doc Martens, I would. Now I’d look like a fashion victim.”


Kim Kardashian, 2013

1 out of 4 Annas.
1 out of 4 Annas.
Kevin Mazur/WireImage

THEME: “Punk: Chaos to Couture”
Kim Kardashian has turned into a Met Gala icon, known for her stunning looks. But the star’s first appearance at the party was controversial — both because some people thought she shouldn’t be there (she was the plus-one of then-boyfriend Kanye West) and because the pregnant Kardashian looked uncomfortable in this completely covered-up floral look by Givenchy’s Riccardo Tisci.

BC: “This was a moment when Kim Kardashian was just not fashion. Kanye was
dressing her up. I will give her points — it’s not easy to dress up when you’re that
pregnant.”

MR: “I felt awful to read that Kim cried on the way home when she read all the
comments on this dress. In retrospect, it wasn’t really that bad. At least it was
covered. People just wanted to pile it on her. There was no way she could win.”


Katy Perry, 2019

4 out of 4 Annas.
4 out of 4 Annas.
Anthony Behar/Sipa USA

THEME: “Camp: Notes on Fashion”
The look that launched a million “Katy Perry’s lit” jokes, this Moschino outfit was built around a “corset consisting of 18 steel bones and two hidden battery packs to illuminate the lights,” designer Jeremy Scott said.

BC: “Talk about costume. Katy’s game for anything. You can’t help but notice her. You know, stars in looks like this have to rent vans to turn up at the Met Gala. You can’t go in a regular car — you have to stand up in that outfit. It’s um … fun.”

MR: “If you’re gonna do costume, you can’t beat this. You have to love that Katy will allow herself to be this silly. She understands the fun of fashion. No one else could have pulled this off. She looks like [Lumiere] from ‘Beauty and the Beast.’”


Lil’ Kim, 1999

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

THEME:” Rock Style”
To make this Barbie-pink Versace number work, Lil’l Kim donned python boots straight from the runway in a model’s size 8 — even though her actual size is a “4 1/2 or 5.” According to the rapper, Bobby Brown said of her: “What’s up with her feet? I know she ain’t that little with big ass feet.”

BC: “That fur coat in pink! She would not be able to walk into the Met Gala today in
a fur coat. The reference is [the 1968 sci-fi movie] ‘Barbarella,’ done in a hip-hop way. There’s snakeskin, a bikini and her hair: a great textural contrast.”

MR: “The Met Gala was very different in 1999. Do I think wearing a bikini to any kind of a ball is good? Not so much. But there is something incredibly fabulous about a pink fur coat. Her abs are the showstopper.”