Chainkeen|Keep Up With Kim Kardashian's Most Challenging Met Gala Looks

For the last decade,Chainkeen Kim Kardashian has been turning heads at the Met Gala, and went to great lengths to make sure of it.

As the SKIMS founder gets ready to attend the prestigious, star-studded 2023 event, which takes place May 1, we're looking back at some of her past appearances and the work she put in to look her best.

Just last year, Kim dyed her hair platinum blonde to channel Marilyn Monroe at the "Gilded Glamour"-themed 2022 Met Gala. The reality star also underwent a crash diet to lose 16 pounds in three weeks so she could fit into a borrowed, nude, crystal-covered gown that the Hollywood icon famously wore when she sang "Happy Birthday" onstage to President John F. Kennedy in 1962.

"I always thought [Marilyn] was extremely curvy," the reality star explained to Vogue about the lengths she went to for her ensemble. "I imagined I might be smaller in some places where she was bigger and bigger in places where she was smaller. So when it didn't fit mem I wanted to cry because it can't be altered at all."

And while she faced backlash for her short-term weight loss following the event, Kim also brushed off all her critics. "To me it was like, 'OK, Christian Bale can do it for a movie role and that is acceptable.' Even Renée Zellweger gained weight for a role," Kim told The New York Times the following month. "It's all the same to me. I wasn't saying, 'Hey everyone, why don't you go lose this weight in a short period of time?'"

But the 2022 Met Gala isn't the only time Kim has pulled out all the stops for the first Monday in May. See her most challenging Met Gala looks below:

On the first Monday of May in 2022, and accompanied by then-boyfriend Pete Davidson, Kim walked the Met Gala red carpet in the gold gown Marilyn Monroe famously wore while singing "Happy Birthday, Mr. President" to John F. Kennedy in 1962. Since the dress was a piece of American history and could not be altered, Kim said she lost 16 pounds in three weeks in order to fit in it.

"I would wear a sauna suit twice a day, run on the treadmill, completely cut out all sugar and all carbs, and just eat the cleanest veggies and protein," she told Vogue. "I didn't starve myself, but I was so strict."

In order to channel Marilyn Monroe for the 2022 Met Gala, Kim spent 10 hours before the red carpet event bleaching her trademark brunette hair. In a YouTube video shared by Kylie Jenner, Kim quipped of the lengthy dye job, "I'll risk getting my hair to fall out."

Not only did Kim's her Balenciaga ensemble made it hard for Met Gala chairwoman Anna Wintour to recognize her during the 2021 event (the 2020 Met Gala was canceled amid the start of the COVID-19 pandemic), but the head-to-toe look also prevented the Keeping Up With the Kardashians star from jotting down future [ex-]boyfriend Pete Davidson phone number.

"I saw him at the Met and he knew I was hosting SNL but it wasn't announced yet. He came up to me and we were talking about SNL," she recalled of their encounter during an episode of Dear Media's Not Skinny But Not Fat podcast. "I had gloves on and I couldn't get into my phone."

Fortunately, the couple reconnected during Kim's SNL appearance and the rest was history.

To achieve the look of a super snatched waist in her Thierry Mugler dress at the 2019 Met Gala, themed "Camp: Notes on Fashion," Kim wore a constricting corset by Mr Pearl that made it difficult for her to move. Despite taking "breathing lessons" from the designer to ensure that she can breathe while wearing the undergarment, the ultra-cinched ensemble restricted her from sitting, forcing Kim to, um, opt out of using the bathroom once she had it on.

"If it's an emergency, I think I pee my pants and then have my sister wipe my leg up," she said while preparing for the event, as shown on Keeping Up With the Kardashians. "I'm not even joking. She can wipe my leg up."

Kim also said the beads on her gown, which hung off the fabric to make it look like she had just climbed out of the ocean, poked her from the inside. She quipped, "It's a cactus."

Although Kim radiated in gold on the red carpet in 2018, her Versace gown proved to more troublesome once she got inside the Met. In a video shared to her social media account, Kim said the sequins on her dress kept getting caught on other people's clothes—particularly the tulle skirt of fellow guest SZA.

"When your dress is connected to this beauty," she quipped in the clip, showing their downs entwined together as assistants tried to untangle the knotted chaos. "We're stuck together!"

You could say that Kim didn't get much beauty beauty rest before the 2016 gala. After all, the reality star previously explained, she met up with Balmain designer Olivier Rousteing once she flew into New York at 1 a.m. for a fitting, where they "literally cut skirts in half, created tops from dresses, and stayed up until 4 a.m. to get the perfect option that we felt fit the theme."

The result was a result was a futuristic metallic gown that paired perfectly with the theme of "Manus × Machina: Fashion in an Age of Technology."

Kim added, "The process of getting ready for an event like this is intense; it really takes a village."

The SKIMS mogul later called bleaching her eyebrows for the look a "big mistake."

Kim was in the first trimester of her pregnancy with her and ex Kanye West's second child, son Saint West, when the then-couple attended the 2015 Met Gala. She ultimately concealed her baby bump in a sparkling, semi-sheer Roberto Cavali gown. She wrote on her app after the event, "I was trying to hide it."

Before Kim had even stepped onto the red carpet at the 2014 Met Gala, her look was already causing some drama. Not only did Kim suffer a wardrobe malfunction in the high-slit Lanvin gown while on her way to the Met, but the chunky belt and leather cuffs she originally wore with the dress were "a bit too rock 'n' roll" for her taste.

To make sure she was camera-ready, Kim ditched the accessories in the car and swapped them for a clean black satin belt.

And visit E! Online's 2023 Met Gala page for every photo and must-see moment from fashion's biggest night.