Kylie Jenner's Biggest Wardrobe Malfunctions

Even fashion icons like Kylie Jenner aren't immune to wardrobe emergencies. We may not often see it, but behind the veneer of picture-perfect pouts and Insta-glam lies someone with regular girl problems involving everything from broken zippers to clumsily spilled drinks. It just goes to show that wardrobe malfunctions are great levelers, putting Forbes' "youngest self-made billionaire ever" on par with the rest of the world. In all her years of being a pop culture phenomenon, the youngest Kardashian-Jenner sister has faced her fair share of fashion mishaps — in front of a global audience, no less. It's the price she pays for belonging to a family famous for being famous. But it seems like the seasoned socialite has grown to revel in her public existence by taking it ever so lightly. 

Alongside press headlines that catalog her wardrobe malfunctions, Jenner has documented many an accident for social media herself, giving her massive following a peek into the imperfections behind her perfect image. This was especially true during her teenage fame as King Kylie, a mostly online era she has described as being "less about what I was wearing, and more about how I felt" (via Vogue). "I just felt confident, free, and I didn't care what anyone said." Such candor has been characteristic of her social media chronicles where even the most embarrassing wardrobe backfires have made it into the public eye. Here are Kylie Jenner's biggest wardrobe malfunctions and how she dealt with them like a pro. 

Kylie Jenner's 2018 Met Gala dress ripped at the last moment

Kylie Jenner has an abundance of iconic looks to her name. Her 2018 Met Gala dress stands out among them as one of the most memorable. Just three months after giving birth to her firstborn Stormi Webster, the beauty mogul made a grand entrance on fashion's biggest night with her legendary curves on display in a figure-hugging gown. The velvet number from Alexander Wang, which featured a long train, was all-black save for a silver zipper detail on the side. While it accentuated the gown rather seamlessly, the zipper was a last-minute addition to the monochromatic piece — a revelation made by Jenner years later, during a recap of her past Met Gala looks on social media. 

"Fun fact: this dress wasn't supposed to have a zipper but it ripped as I was squeezing into it so we added it on the way out the door," the billionaire shared on her Instagram stories in 2020 (via E! News). Luckily, the quick fix worked out in her favor, completing a look that is counted among Jenner's best red carpet moments. It was also impossible for the anomalous zipper detail to draw attention from the fact that the 2018 event marked the first time that Jenner and her partner Travis Scott officially walked a major red carpet as a couple. As Vogue observed, all eyes were on the fashionable pair once notorious for keeping their relationship out of the spotlight. 

New moms will relate to her stained t-shirt moment

Kylie Jenner would not have expected to begin lactating while filming a TikTok video. But it happened — and the socialite handled it like a boss. Just months after giving birth to her second child Aire Webster in 2022, Jenner took to social media to clap back at trolls who took aim at one of her previous makeup tutorial videos, accusing her of trying too hard to seem relatable. "I think some people thought that it was, like, fake or that I really don't drive myself, which is just silly," the beauty guru told followers in a subsequent video, before proposing the idea of a series called "Kylie in the Kar" (via The Independent). 

Jenner was promoting a new lipstick collection, but it was hardly the highlight of the video. The entrepreneur ended up impressing fans with how calmly she handled the appearance of a stain on her t-shirt in the middle of her recording, pausing only to react with a nonchalant "Oh, looks like I'm lactating." She went back to filming the rest of her TikTok right after, ending her video by coolly announcing, "I'm going to go, maybe change my shirt now." Jenner, who had her first child at 20, has been more than candid online about her motherhood journey. Describing her postpartum experience after having Aire, she told her Instafam: "It's not easy mentally, physically, spiritually ... it's just crazy" (per Life & Style). 

This Oscars dress severely restricted her movement

If it's not uncomfortable, is it really high fashion? Kylie Jenner bore the cost of bedecking a super glamorous gown for the 2020 Oscars after-party by compromising the free use of her torso. The young entrepreneur was a sight to behold in the figure-hugging, jewel-encrusted Ralph and Russo piece that she walked the red carpet in. Unfortunately, that was the only movement she could elegantly manage in the gown, which was evidently tailor-made for upright activity. 

The dress didn't allow for much motion, according to Jenner, who could barely sit in it. An Instagram snap showed her reclining on a seat in the stiff dress, smiling through the discomfort. She summed up the experience in a single statement: "Couldn't really sit in this but it was worth it" (via Harper's Bazaar). Luckily for Jenner, that wasn't her only look for the party hosted by Vanity Fair. The beauty mogul switched out her blue gown for a more flexible-looking, red-hot number from Vivienne Westwood for the night. 

The Kardashian-Jenner clan isn't unfamiliar with restrictive dressing. Back in 2019, Jenner's sister Kim Kardashian donned a waist-cinching Thierry Mugler gown that attracted massive controversy for the kind of rigid beauty standards it promoted. Forget sitting: It was a dress that Kardashian admittedly couldn't properly breathe in. For the sake of the dress — which took seven months to make — Kardashian had to take corset breathing lessons (via Instagram). 

Getting out of her Christmas dress was not a sexy affair

Christmas 2018 was an adorable affair for Kylie Jenner and baby Stormi Webster, whose coordinated sparkly outfits were just too good to be true. That is until it was time for Mama Jenner to tuck her daughter into bed. Designer Yousef Aljasmi would never have imagined that the functional value of his dazzling creation would extend to domestic duties. But Jenner, ever the committed mommy, managed it like a pro. All through her nightly routine of bathing Stormi, the beauty mogul stayed firmly put in her gown (thigh slit, trail, et al). It was doubtless an impressive feat but one that she achieved more out of compulsion than choice. 

As it turns out, Jenner was unable to slip out of her dress as easily as she had slipped into it and even required some assistance to get it off. Extravagance is a trademark of Kardashian-Jenner Christmas parties, so this over-the-top moment from Jenner was hardly surprising. And the malfunction barely killed her mood. "This is me leaving the party early to go give my baby a bath (while wearing this dress because i couldn't get it off by myself) and put her to sleep and it was the best xmas eve yet," Jenner wrote on Instagram, alongside a picture of herself and Stormi twinning (via Elle). Well, guess we know the Christmas miracle she wished for that year! 

Jenner's dress slipped dangerously low during a TikTok video

When an outfit is low-cut, a wardrobe malfunction is never too far away. Kylie Jenner nearly suffered one while making a TikTok video in 2022, when her top slipped down a little too much on camera. Jenner was bare-skinned, save for the black material that covered her chest, according to Life & Style. But hand it to the social media sensation to handle the situation like a pro! Unfazed, Jenner continued recording even as she held her outfit together to prevent it from revealing too much. It's not the first time — far from it, in fact — that shutterbugs have anticipated a malfunction when it comes to Jenner.

With the kind of risqué wardrobe the beauty queen owns, dressing up in her stylish best can often be a gamble. Jenner was supposedly on the verge of a fashion misstep in her show-stopping blue gown at Paris Fashion Week 2022, The Sun noted. The stunning velvet number by Schiaparelli, widely described as a daring choice, showed off a plunging neckline that went all the way down to Jenner's waist. Unsurprisingly, Jenner carried off the look effortlessly. This wasn't the case with another low-neckline outfit she wore to the opening of the Sugar Factory. "There's a lot of duct tape under this dress holding these suckers up," she revealed about the sheer dress in a now-deleted post on Instagram (via ET Online). 

She spilled a drink in the most awkward place ever

Kylie Jenner has never been more relatable than when she was the victim of a wardrobe malfunction that we've all probably faced at some point in our lives. In an episode that occurred during her King Kylie era in 2016 — widely remembered by pop culture nuts for showcasing the billionaire's life at its candid best — Jenner suffered an unfortunate spill on her jeans mid-outing with her friends (via E! News). The influencer's stars were seemingly unaligned that fateful day, considering how the spilled drink aligned on her crotch, basically making it look like she had wet herself. "Why does this always happen to me?!" she exclaimed on Snapchat, where the entire incident was recorded for posterity. "I always spill my drink," she wrote.

Over multiple videos, Jenner's Snapchat followers were treated to the star's shenanigans in her wet denim. At one point, the social media mogul even gave fans a full view of her posterior, asking her friends if her jeans looked okay from behind. And like any supportive pals would, Jenner's companions assured her (with giggles galore) that it was all A-okay, even as a huge stain stared back at them. Thankfully, the nature of the mishap meant that the problem would hopefully have resolved itself soon after. In any case, it made for quality content that was more memorable than it was embarrassing. 

Her gorgeous silver Met Gala gown physically injured her

Whoever said beauty is pain wasn't kidding around — and Kylie Jenner is a living, breathing testament to that. The beauty mogul's life usually comes across as a luxurious fever dream that many aspire toward. Off-camera, things aren't always so easygoing. Giving fans a peek into the price she pays for being one of the most sought-after fashion figures in the world, Jenner shared behind-the-scenes glimpses of her first Met Gala appearance in 2016. The glittering Balmain gown she wore was a total stunner and won unanimous praise across Best Dressed lists. What the public didn't see, however, was the physical distress it caused the 18-year-old. 

Taking to Snapchat after the elite event, Jenner shared a snap of her bruised legs, writing: "When ur dress made you bleed and ur feet are purple" (via Teen Vogue). Not one to take the demands of being a diva lightly, Jenner braced through the repercussions of wearing a gorgeous but surprisingly vicious gown with her best game face on. And, according to her post-Met review, her injuries were supposedly worth the trouble she went to. (The things we do for fashion!) Nevertheless, Jenner's Met debut clearly made an impact, opening the doors for her to earn a regular invite to the coveted charity show in consecutive years. 

She dealt with a broken zipper in the most tactful way

Kylie Jenner seems to have a love-hate relationship with zippers. While they saved her torn outfit at the Met Gala in 2018, the apparatus betrayed her dramatically a few years before that in 2016. The makeup mogul had donned a skintight jumpsuit for a night of Hollywood partying with her A-list girl gang, which included the likes of Gigi Hadid and Hailey Baldwin (per E! News). A hot number from the fashion brand House of CB, the outfit had a much-talked-about upper body cutout. Before long, though, the jumpsuit revealed more than originally intended when the zipper on its back snapped. 

The world would never have come to know about Jenner's ordeal had she not documented it for the public to see on Snapchat. Her post showed someone attempting to salvage the ripped dress, but it appeared that they weren't entirely successful, given that Jenner exited the restaurant with a denim jacket draped over her back. The minor malfunction, however, did not distract from the classic Jenner razzmatazz she exuded most noticeably through the glaring cutout detail on her jumpsuit. In fact, the jumpsuit look marked one of the first few instances of the social media star impressing fans with skin-baring outfits that put her now-famous underboob-highlighting style on display. 

Her leggings turned out to be a bit too sheer

Kylie Jenner is no stranger to sheer fashion. In fact, the famous socialite is universally acknowledged for always acing the precarious trend like no one else can. Well, almost always. Back in 2015 — when she ventured into entrepreneurial fame with her internet-breaking Kylie Lip Kits — the young businesswoman seemingly suffered a faux pas, thanks to a pair of pants that revealed more than they covered. Post what must have been a grueling workout session — given her rock-hard abs — Jenner was papped leaving the gym looking as suave as ever in black-and-white workout clothes, complemented by her once-iconic green tresses. Flashing camera lights, however, captured more than Jenner may have intended them to, rendering her leggings nearly transparent. 

An unruffled Jenner confidently continued toward her car, making shrewd use of her phone and purse to cover her anterior and posterior, according to Cosmopolitan. The accessories stayed in place right till the moment Jenner stepped into the waiting vehicle. It was one of several hits-and-misses Jenner has had with sheer leggings; another headline-making malfunction came to pass just a year later when Jenner visited her brother-in-law Lamar Odom at a Nevada hospital in what OK! Magazine! noted was a pair of see-through pants. Nevertheless, these wardrobe oversights did little to dent Jenner's status as an experimental fashion queen with many a skin-baring sheer outfit to her name.