Kim Kardashian’s Most Challenging Fashion Looks: From Daring To Wear

View gallery Image Credit: Stephen Lovekin/BEI/Matt Baron/Shutterstock

For Kim Kardashian, style is everything. The reality diva, 41, has always been willing to push the fashion limits, even if that means she’s a bit uncomfortable. Whether it’s skyscraper-high stilettos, a dress that’s too tight to walk in, or an outfit concept that completely covers her famous face, Kim’s never turned down an opportunity for a chic moment.

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Kim Kardashian attends the 2019 Met Gala in Thierry Mugler (Shutterstock)

The starlet admitted she’d do basically anything for a good look while visiting The Ellen DeGeneres Show in April 2022. There, the queen of Calabasas claimed she would “literally wear” whatever. “I don’t care how uncomfortable, I don’t care how long, if I have to wear a diaper and not go to the bathroom — I don’t care what I have to do,” she said. Now, that’s commitment.

Ready for all of Kim’s most outlandish looks? From her blacked-out Balenciaga look at the 2021 Met Gala to the impossibly tight Dolce & Gabbana dress she wore for their debut fashion collab in 2022, check out the star’s most impractical fashion moments here.

Milan Fashion Week In 2022

The diva could barely move in her silver Dolce & Gabbana dress during Milan Fashion Week 2022 (NGRE / BACKGRID)

Kim debuted her Dolce & Gabbana collaboration, titled “Ciao, Kim”, during Milan Fashion Week 2022, and absolutely lit up the night at the after party on Sept. 24 in a dazzling, body-hugging, silver sequin gown that featured a plunging, lace-up front. While the dress was absolutely stunning, there was one problem: Kim could barely walk in it! A TikTok posted by the SKIMS founder’s longtime friend Stephanie Shepard, 33, showed Kim hopping up the stairs because she could barely move her legs. Helping hands finally came to Kim’s rescue and assisted her as she slowly teetered up seemingly never-ending flights of stairs. Once she got to the black SUV waiting to drive her home, she had to be pulled into the car and could not sit properly because her dress was so tight. At least Kim and her fans got a laugh out of it!

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The Met Gala In 2022

She caused controversy channeling Marilyn Monroe at the 2022 Met Gala (Shutterstock)

Kim’s 2022 Met Gala dress was the subject of a lot of controversy. She donned Marilyn Monroe’s gorgeous, pearl-covered dress she wore to sing “Happy Birthday” to John F. Kennedy and the Democratic National Committee at NYC’s Madison Square Garden in 1962, and although it appeared to fit Kim like a glove, that was reportedly not the case. The dress, first of all, did not close all the way, hence why Kim wore the furry white shawl with it. Secondly, rumors that Kim actually damaged the dress because it was so tight circulated around the internet, and social media trolls made their anger known. However, both Kim, and Ripley’s Believe It or Not! in Orlando, Fla., which owns the multi-million dollar dress, shut down the rumors right away.

“We hear you! Kim Kardashian’s walk up the Metropolitan Museum’s stairs at this year’s Met Gala has caused quite the stir, but one thing it did not directly cause is the reported damage to Marilyn Monroe’s famed ‘Happy Birthday’ dress from 1962,” Ripley’s said in a statement following the harsh criticism. They added, “There is no disputing the fragility of the dress and there was a calculated risk associated with wearing it, but Ripley’s has been collecting notable pop-culture memorabilia … for over 100 years. … No matter which side of the debate you are on, the historical importance of the dress has not been negated, but rather highlighted.”

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Furthermore, Kim revealed to Vogue just before she walked up the Met Gala’s famous steps that she was very careful with the beloved dress because she understands how historically important it is. “I’m extremely respectful to the dress and what it means to American history. I would never want to sit in it or eat in it or have any risk of any damage to it and I won’t be wearing the kind of body makeup I usually do,” she said in the interview.

The mom of four also revealed she changed into a replica of the dress for the actual gala, something she further elaborated while on the TODAY show. “I showed up to the red carpet in a robe and slippers and I put the dress on at the bottom of the carpet, went up the stairs — I probably had it on for three minutes, four minutes,” she explained, per the New York Post. “And then I changed right at the top of the steps.”

Kim also upset fans when she revealed she lost 16 pounds so she could squeeze into the dress. “I had this idea to put it on and try it on and they came with armed guards and gloves. I tried it on and it didn’t fit me. I had to lose 16 pounds down today to be able to fit this,” she told La La Anthony on the red carpet. “It was such a challenge, it was like a role. I was determined to fit in it.”

Kim recalled in more detail what she went through to fit into the dress in her chat with Vogue. “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 noted. “I didn’t starve myself, but I was so strict.” Kim said she “wanted to cry tears of joy” when the dress finally slipped up her petite, but famously curvy frame.

Unsurprisingly, Kim got backlash for her dieting comments as well, but her trainer DON-A-MATRIX defended her weight loss and said he was there the entire time monitoring her progress and her health. “She works really hard. I was there during the process. It wasn’t like a ‘starving yourself’ thing,” he explained.

Paris Fashion Week In 2022

Kim put everyone on high alert with her yellow Balenciaga caution tape look at Paris Fashion Week in March 2022 (Best Image/BACKGRID)

Kim turned heads at Balenciaga’s fashion show at Paris Fashion Week in March 2022 when she wore a bodysuit completely composed of yellow caution tape. However, instead of reading “CAUTION”, the  tape had the Spanish fashion house’s name printed across it in black. The tape covered her entire body, from her neck to the points of her boots, just leaving her hands and face free. While she could walk in the outfit, unlike some of her previous looks, it was certainly a fragile piece!

After Hosting SNL In 2021

Kim Kardashian wore pink feather Balenciaga after her ‘SNL’ hosting debut in Oct. 2021 (Splashnews)

The Kardashians star hosted Saturday Night Live in Oct. 2021 and celebrated her successful gig at its wrap party looking pretty in pink. She stunned in a super tight, super pink catsuit she accessorized with a luxurious boa shawl. Her boots were one in the same with the leotard and it begs the question: How did she go to the bathroom? Perhaps this was one of those nights she opted for a diaper!

The Met Gala In 2021

Kim collaborated with Balenciaga creative director Demna Gvasalia on her black-out look for the 2021 Met Gala (Shutterstock)

Can you see where you’re going, Kim? The  SKKN creator arrived at the 2021 Met Gala donning an all-black Balenciaga outfit completed with a long-sleeved shirt, leggings, a high-low dress, gloves, boots, and a face mask that left absolutely none of her skin showing. The only part of Kim outside the black outfit was her black hair. The question of the night, of course, was whether or not she could see out of her dress, and according to her, she could — well, sort of.

“Kendall was calling my name and I couldn’t see who it was. But I saw the outline of her sparkly dress [and knew it was her],” she revealed on her Instagram Story following the big event, per Us Weekly.

The Met Gala In 2019

Kim’s stunning Met Gala dress in 2019 can be seen at the top of this list. The skin-tight dress was by Mugler and was decorated by beads meant to look like water droplets dripping off her curvy figure. Her waist was super cinched and tied off with a bow, leaving fans asking not if she could walk or see, but if she could breathe! It turns out it was a bit hard to.

According to a video with Vogue that showed Kim’s last dress fitting, she revealed it took three people to lace up her corset tight enough to get the super cinched effect they were looking for. She also joked to Vogue‘s editor-in-chief, Anna Wintour, that if she does not sit down for dinner, there is a clear reason why. “I’ll be walking around, mingling, talking, but I cannot hardly sit,” she said.

Later in the video, she also revealed that she will not be able to go to the bathroom in her dress. “Wish me luck, I won’t be able to pee for about four hours,” she noted while getting ready ahead of the special night. “We’re coming up with a plan for what we do in case of an emergency.” Pain is beauty, right?

After The 2019 Met Gala

She looked like a disco ball in blue vintage Mugler after the 2019 Met Gala (Shutterstock)

Kim wore another skin-tight dress to the Met after-party in 2019, but that time, it appears she was without a corset and would be able to head to the bathroom if needed. Kim’s sexy ensemble was a blue latex dress that featured a deep neckline that reached below her belly button. She wore matching boots and gloves to accessorize. The tinsel around the plunging neckline matched the tinsel wig she donned, which surely helped her light up the room.

The Hollywood Beauty Awards In 2019

Kim almost spilled out of her barely-there Mugler dress at the 2019 Hollywood Beaty Awards. (Shutterstock)

Kim’s Mugler dress she wore to the 2019 Hollywood Beauty Awards appeared to defy physics. She donned a gorgeous black gown with a super tiny upper half that looked like it could barely hold her chest in place. A high slit and bracelets that matched her dress completed the daring look. Luckily, no wardrobe malfunctions were reported at the event.

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