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1Rihanna, 2015

Four years ago, Rihanna wore what would become one of the most talked-about Met Gala gowns of all time. For the exhibition "China: Through The Looking Glass," the singer stunned in an ornate fur-trimmed yellow gown by Chinese couturier Guo Pei. The dress took 20 months to make, weighed a total of 55 lbs, and made for the grandest of entrances on those iconic Met Gala steps.
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2Cher, 1974

Cher was one of the first to rock the naked dress, paving the way for future red carpet style at the 1974 "Romantic and Glamorous Hollywood Design" Met Gala. The singer's nude, bedazzled Bob Mackie gown featured a white feathered hemline and sleeves and went on to inspire countless nearly-nude looks in the decades to follow.
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3Amber Valetta, 2004
In 2004, the Costume Exhibit celebrated fashion from the 18th century. For the occasion, Amber Valetta took the theme quite literally, showing up as an early-2000s version of Marie Antoinette.
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4Madonna, 2016
Always one to push boundaries, Madonna called her sheer Givenchy look at the 2016 Met Gala a political statement meant to fight ageism. "When it comes to women's rights we are still in the dark ages. My dress at the Met Ball was a political statement as well as a fashion 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," the singer wrote on Instagram.
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53LW, 2001
Though attendees don't always adhere to the theme of the Costume Institute, perhaps the wildest interpretation was 3LW showing up to 2001's "Jacqueline Kennedy: The White House Years"-themed event in matching skin-tight yellow-and-blue ensembles. Maybe they missed the memo on the Jackie O. theme or maybe we missed the former First Lady once wearing a yellow belly shirt and body glitter, but either way, it was a head-turning choice.
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6Frances McDormand, 2018
Getty ImagesFor the "Heavenly Bodies: Fashion and the Catholic Imagination" theme, Frances McDormand transformed into a heavenly fashion angel in a Valentino Couture look and butterfly headdress.
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7Sarah Jessica Parker, 2013
Though the "Punk: Chaos To Couture" theme should have given us more outrageous red carpet looks, Sarah Jessica Parker was one of the few who stood out in a conversation-starting look. The actress wore an ornate gold-and-black mohawk headpiece that became one of her most memorable Met Gala getups.
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8Diana Ross, 2001
The legendary Diana Ross brought her own disco style to the 2001 event with an over-the-top black tulle headpiece that stole the show. Though the theme was Jackie Kennedy's White House, Miss Ross always adheres to her own rules—and looked fabulous while doing so.
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9Katy Perry, 2018
Getty ImagesTaking the "Heavenly Bodies" theme quite literally, Katy Perry showed up to the 2018 Met Gala dressed as a life-size angel, complete with giant feathered wings. The custom Versace look gave the Victoria's Secret Angels a run for their money.
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10Marc Jacobs, 2012
Proving naked dresses are also for the boys, Marc Jacobs showed up to the 2012 Met Gala in a see-through black lace shirtdress that showed off his white boxers. The designer's look marked one of the few times a man has dared to wear the naked dress look on the red carpet—and he completely slayed.
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11Julie Maclowe, 2017
Julie Maclowe went for a bold plaid ensemble at the Rei Kawakubo/Comme des Garçons-themed event. To this day, it remains a mystery as to where exactly her arms went in this look.
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12Iman, 1997
For an evening honoring Gianni Versace, Iman stunned in a floor-length gold lamé coat with feathered detailing, topping off the grand look with a diamond tiara. Real fashion royalty.
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13Beyoncé, 2015
No stranger to shutting things down on the red carpet, Beyoncé dropped jaws when she showed up to the 2015 Met Gala in a completely naked dress adorned with crystalized beading. She topped off the look with a fierce side ponytail that only Queen Bey could pull off.
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14Jaden Smith, 2017
In a move that confused literally all of us, Jaden Smith carried his cut-off dreadlocks as an accessory at the Rei Kawakubo-themed Met Gala in 2017. Known to push boundaries when it comes to fashion, the teenager once again surprised us all with his outrageous accessory choice.
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15Lady Gaga, 2016
In a look true to Gaga's signature style, the singer showed up to the "Manus x Machina: Fashion In An Age Of Technology"-themed ball sans pants. She topped off the futuristic blazer and bodysuit by wearing the highest platform boots to ever hit the red carpet.
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16Daphne Guinness, 2011
In 2011, the Costume Institute honored the late Alexander McQueen. For the occasion, the designer's close friend and muse, Daphne Guinness, wore one of his iconic feathered designs and sky-high platform heels—like a high-fashion bird of paradise.
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17Sarah Jessica Parker, 2015
It was the headpiece that sparked a million memes. SJP is a master of dressing for Met Gala themes and her look for 2015's "China Through The Looking Glass" ball didn't disappoint. Although her over-the-top headwear started endless "flames" jokes on Twitter and Instagram, SJP told BAZAAR she put a lot of hard work into her look. "I researched that for a really frickin' ass long time. I studied Chinese opera, ballet, theater, design, costume design. I studied tassels, poms-poms, silk...I think people forget there is a theme; it is a costume ball."
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18Kendall Jenner, 2017
Showing off some serious skin, Kendall Jenner dropped jaws at last year's Met Gala when she wore nothing but a black thong and sheer gown on the red carpet. The La Perla look left little to the imagination and marked one of the model's most daring dresses to date.
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19Rihanna, 2017
Always one to show up and slay the Met Gala theme, Rihanna once again won the night in this avant-garde Rei Kawakubo look. The dress, which the singer paired with over-the-knee lace-up gladiator heels, was actually featured on display in the Costume Exhibit that year, too.
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20Naomi Campbell, 2001
Getty ImagesThe theme was "Jacqueline Kennedy: The White House Years" and Naomi Campbell showed up in a bedazzled "Like a Virgin" t-shirt. Iconic.

Lauren Alexis Fisher is the Senior Editor at Cosmopolitan, overseeing digital content across fashion, lifestyle, beauty, sex, and culture. Previously, she was the Market Editor at Harper’s BAZAAR and has written for publications including WWD, Bustle, and W Magazine. When she’s not busy taste-testing her way through every dirty martini in New York, you can follow her on Instagram for bad jokes, good outfits, and annoying vacation pics.
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