The Most Shocking Outfits Kylie Jenner Has Ever Worn

Kylie Jenner is the human embodiment of glam. Among the things that stand out about the star — besides her impressive net worth – is the spectacular style evolution over the years. She was only 10 when she made her screen debut in 2007, starring in her family's reality show "Keeping Up with the Kardashians" (via Insider). She has since emerged to the fore as one of the most powerful members of the Kardashian-Jenner clan. 

The makeup mogul has her fingers dipped in many successful namesake businesses — from Kylie Cosmetics to Kylie Swim — that cater to the fashion industry. So, needless to say, all eyes are forever on her own wardrobe! And she always delivers, turning even the most mundane moments into literal show-stopping events. As her sister and fellow fashionista Kendall Jenner put it in an interview for Harper's Bazaar, the socialite "can wear a full-blown gown to lunch." As Jenner is so willing to experiment with trends and forge her own path in fashion, some of her ensembles have undoubtedly been shocking, to say the least.

Kylie Jenner has made an impression at the Met Gala Ever since she began attending what is regarded as fashion's biggest night (via People). 2018 marked a show-stopping appearance by the then-20-year-old, who attended only months after welcoming her first child with boyfriend Travis Scott. The new mom opted for a figure-hugging, black Alexander Wang gown that flaunted a midriff cutout and distinct zipper designs on the side, as noted by Harper's Bazaar.  

Turns out, that noticeable zip detail was apparently a last-minute add on! On social media two years later, Jenner made a surprising revelation about her 2018 dress. "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," she wrote (via E! News). "But it worked out, I love it."

In a breakdown of her gown, Vogue claimed that Jenner's outfit tapped into staple elements from her own wardrobe — velvet tracksuits, for instance — and even had a hint of sportswear, bringing attention to the zippers that you now know the story behind.

Kylie Jenner knows how to serve a look — and really garnish it too! The beauty queen arrived looking extravagant at the 2019 Met Gala red carpet, in keeping with the theme that year, Camp: Notes on Fashion. As explained by Vogue, the memo called for campy stuff that overdosed on the element of excess. Jenner, then 21, appeared to nail the summons in a lilac-colored Versace gown that drew inspiration from showgirl culture, completing the look with a similarly-shaded wig and dramatic feather sleeves. As striking as she looked, Jenner admitted she "couldn't breathe a little bit" in her dress! Her supermodel sister Kendall Jenner went for a similar look but in blazing orange. 

It was hard to miss their in-your-face feathery detail and it caught the eye of the nonprofit People for the Ethical Treatment of Animals (PETA). In a statement, PETA took a jab at the Met Gala attendees, saying, "Feathers are just as cruel as fur." Though the rebuke included others, like Naomi Campbell, who also sported feathery fits on the red carpet, it made sure to add a pointed mention of the sisters: "We're looking at you, Jenners." In a behind-the-scenes video for Vogue, it was later disclosed that Jenner's lilac sleeves were made of ostrich feathers.

If Christmas coincides with a Kardashian gala, you better believe the affair will have double the sparkle! The annual Christmas Eve party was hosted at former couple Kim Kardashian and Kanye West's Los Angeles home in 2018 and is reported to have cost a dazzling $1.3 million. There was only one thing about the celebrations that outshone the price point: Kylie Jenner's bejeweled silver gown, slit stylishly along the thigh. And perfectly complementing the blinding shimmer of Jenner's crystal dress was her baby, Stormi Weber, who twinned with her mommy in an adorable matching silver ensemble — with the added detail of mini Nikes (via Seventeen). Our vote for showstopper goes to the little one, hands-down!

According to Elle, the mother-daughter duo's coordinated set was the creation of Kuwaiti designer Yousef Aljasmi. While baby Stormi was all party-ready in her comfy sneakers and practical pants, her mom's wardrobe that night apparently wasn't as convenient. Taking to Instagram stories, Jenner shared a snap in which she cradled Stormi, and revealed alongside, "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." Well, there's no passion without pain, is there? 

Kylie Jenner glittered (as she always does) at the Oscars afterparty in 2020. Wearing a navy blue Ralph & Russo gown encrusted with crystals and embellished with an eye-catching appliqué, Jenner walked into the Vanity Fair-hosted event at Beverly Hills, exuding oomph. But looking as exquisite as Jenner did comes at a price! The socialite took to her Instagram back then to reveal the effort her fit took that night. As quoted by Elle, she revealed she "couldn't really sit in this but it was worth it." She apparently had to seat herself horizontally in the car on the way to the event, according to People. 

Jenner, perhaps anticipating the dysfunction of the dress, slipped into a different outfit later that night. Comfort above all! As noted by Harper's Bazaar, once she was off the red carpet, Jenner traded in her navy blue for a ravishing red piece by Vivienne Westwood that had a slit running up her thigh. According to E! News, the red fit was what Jenner wore to her second awards afterparty — the one hosted by star couple Beyoncé and Jay-Z. Jenner attended the glitzy bash with sisters Kim, Kourtney, and Khloé Kardashian.

Is it a dress? Is it a trench coat? An outfit is what Kylie Jenner says it is! Not long after becoming a mother, the stylish diva hit the MTV Video Music Awards red carpet in 2018 to cheer on beau Travis Scott, sporting a blazer that served as a dress. The simple yet chic outfit was a Tom Ford creation, according to Bustle, and gave the star a Barbie-esque look. A statement encrusted belt accentuated her waist and her golden locks were pulled back into a sleek bun — it's true what they say, less is more! That she ditched pants altogether, as Teen Vogue noted, could have given fodder to internet trolls but her minimalism worked in her favor and was unanimously upvoted. 

Nevertheless, Seventeen sniffed out a bit of repetition with Jenner's hit red carpet style. The outlet reported that her white ensemble looked vaguely similar to the fit Jenner went with on her 21st birthday earlier that month. Though the hot pink number was more a dress than a blazer, it was hard to miss minor similarities between the two ensembles — both flaunted structured shoulders and an accented waist detail. But hey, no one's complaining, because the makeup mogul rocked both styles with equal oomph! 

Go big or go home, right? Kylie Jenner's extravagant outfits forever radiate that energy, especially at red carpet events when the socialite dresses to impress. In keeping with that tradition, her 2019 Grammys fit made a loud and bold (and rather pink) style statement. For her debut outfit at the music awards night, the reality star opted for a Balmain ensemble that consisted of a full-length bubblegum pink jumpsuit, with a dramatic sleeve design that was impossible to miss (via Harper's Bazaar).  

Vogue noted that the style icon stayed loyal to the original design of the outfit, reportedly conceptualized by Balmain creative director Olivier Rousteing, as it debuted on the ramp in Paris. This meant pulling up even the matching gloves that came with the look. Gloved hands would probably have been a tad bit impractical for the active social media veteran, Vogue seemed to think. The outlet, recording the influx of memes post-Grammys, also made sure to include a netizen's likening of Jenner's outfit to a pink Easter Bunny costume. 

Jenner hasn't been shy about her love of pink though. In an interview with Architectural Digest, she revealed the color was even consciously worked into the design of her Hidden Hills home in Los Angeles, and that she "wanted a lot of it!" 

When Justin Bieber sang, "For all the times that you rain on my parade" in 2015, little did he know he was singing the lyric into existence on an important day of his life that would come four years later. The pop singer married Hailey Bieber in a star-studded ceremony in South Carolina in 2019, with friend Kylie Jenner as one of the guests in attendance (via Harper's Bazaar). A full-time showstopper who makes sure to dress the part — even if it is someone else's wedding — Jenner turned up in a gold foil dress with a chest and thigh cutout that made heads not turn but spin! Insider noted that the single-shoulder look Jenner wore was a J'Aton Couture design, and Jenner was kind enough to share several glimpses on Instagram.

For how distinct the golden number was, it was bound to make some noise on social media — but not all of it turned out to be the good kind. People reported that some netizens were concerned about the star upstaging the bride on her special day. Critics also said the gown was far too revealing for a wedding. However, support simultaneously abounded for the makeup guru as well, with some fans claiming the extravagance was classic Jenner. We dare say that's a valid point! 

Kylie Jenner rung in Halloween in 2020 by invoking the power of the Red Ranger — literally! The makeup mogul and her gang of pals, dressed as the full set of superheroes, kindled a whole lot of '90s nostalgia as the Power Rangers. As pointed out by Elle, Jenner's look was a sexy rendition of the original red-hot Ranger costume, flaunting cutouts on her midriff, paired with a belt, futuristic glasses, and matching wig. She was joined by friends Victoria Villarroel, Anastasia Karanikolaou, Sofia Villarroel, and Carter Gregory for the festivities. 

The young entrepreneur, known for her elaborate Halloween dress-ups each year, took to TikTok to give fans a peek into her themed celebrations that year. But we all know, on social media, there's just no escaping trolls. A comment by one netizen read, "SOMEONE SAID PLASTIC RANGERS PLEASEEEE" (via E! News). Jenner, who is not against offering the odd rebuttal to standout comments, clapped back saying "And we love recycling."

That was also true, in a way at least, for a second ensemble Jenner had planned for the celebrations. The mom of two and her sister Kendall Jenner reached far into their closets to pull out an iconic childhood look — in which the two sported tiny glam fits and dazzling wigs — and recreated it for Halloween, Entertainment Tonight reported. Of course, the 2020 version of their fits was reimagined in quintessential Jenner style, complete with crop tops and thigh slits. 

With the over 300 million followers she boasts on Instagram, it's safe to say that Kylie Jenner's influence is powerful. So when the beauty mogul supposedly failed to tag a Black-owned brand whose dress she gloriously posed in while holidaying in Utah in 2020, it came as a shock to fans who promptly called her out for it. According to Teen Vogue, the ochre and brown design with fishnet detailing was a design from Loudbrand Studios, which belongs to Jedidiah Duyile. 

Apparently, sleuthing fans followed the trail and figured out where Jenner's dress was from themselves. As noted by BuzzFeed, some critics even accused Jenner of "refusing" to tag the brand. Before long, Jenner jumped into the hot oil and tweeted, "ok this is just a reach. why would i ever REFUSE to tag a brand and block comments. this is completely false. i think this brand is amazing and i wanted to show support and will continue to do so," tagging Loudbrand Studios. 

Talking to Teen Vogue, Duyile, then 25, narrated how her piece ended up in Jenner's closet. "We reached out to Kylie's stylist, Jill Jacobs and she fell in love with Loundbrand Studios. We sent over pieces from the new collection unsure if Kylie would wear it but she did!" she said. Thanks to the controversy, Loudbrand Studios' online stock sold out overnight! 

Being a fan of the show "The Handmaid's Tale" is one thing. Replicating it for recreation is a whole other level of dystopia. Kylie Jenner probably didn't expect the massive backlash she got when, in 2019, she threw a party where attendees turned up dressed as the women of Gilead, the fictional country that forms the setting of the Hulu show. Based on an acclaimed novel of the same name by Margaret Atwood, the series shows a future where women — dressed uniformly in red robes and white bonnets — are oppressed in the face of a fertility crisis. 

As per the BBC, Jenner organized the party for her friend Anastasia Karanikolaou. Snaps shared on her social media showed that Jenner, dressed to the theme, even welcomed guests in full Handmaid style, invoking phrases from the series "Praise be." CNN reported that the beauty mogul even designed a menu around the theme, serving up drinks like "Praise Be Vodka." 

However, Jenner didn't garner much praise. Outrage began pouring in quickly, with followers calling her party out for being "tone-deaf" and "disturbing," as reported by Harper's Bazaar. The somber context of the plot was perhaps not the best one to plan a party around! HuffPost claims Jenner did a little cleanup of her social media after to remove evidence of her ever having thrown the controversial party.

Kylie Jenner apparently knows how to laugh at herself! The forever immaculate star, who has not a hair out of place in photos that make it to social media, was caught in a seemingly unflattering moment some years ago. It resulted in a close-up photo of her, complete with her eyes closed and other facial features startlingly close to the camera. The photo went viral on the internet in 2015 (via Us Weekly). 

At the time, the photo became meme fodder but, as goes social media's goldfish memory, its popularity gradually faded over the years. That is, until Jenner herself reminded people in 2016 that it existed. She immortalized the iconic shot for posterity by getting a graphic print of it on a t-shirt, even posing in the fit for a mirror selfie. She posted the picture to Instagram without comment but those who knew, knew.

MTV noted that demands for the t-shirt collectible actually grew after Jenner debuted it. Though the piece didn't figure on any Jenner-Kardashian fashion lines, it's safe to say the young entrepreneur did throw some wisdom out into the world with it — a sense of humor can turn even the most awkward situation on its head! 

Between managing a massive beauty empire and being a full-time social media star, even a style icon like Kylie Jenner probably needs to draw fashion inspo from fellow beauty queens at some point. Or so netizens seemed to think when, in 2019, Jenner sported a leopard-print catsuit that looked vividly familiar. The sheer outfit by LaQuan Smith was reportedly the same one that Barbadian singer Rihanna wore just a month prior, per Page Six. 

As reported, Jenner opted for the $695 fit to promote a new summer range of her Kylie Cosmetics, while the Fenty Beauty founder posed in it for Interview magazine. Many on social media were quick to allege that Jenner's was a copycat piece and that her emulation of the Grammy-winning singer was "creepy" (via Cosmopolitan). In fact, this was not the first time the two women were pitted against each other, wardrobe-wise. (Side note: Both Jenner and Rihanna have dated Travis Scott.)

In 2017, while on vacation, Jenner posed in a fringed silver jumpsuit designed by The Dolls House that closely resembled a similar number in green by L'Impasse Boutique that Rihanna sported at the MTV Video Music Awards a year prior. According to Seventeen, it kicked off a controversy with The Dolls House claiming they had designed both jumpsuits, while L'Impasse threatened to sue for duplication. 

There's nothing like a fashionable yet comfy sweatshirt. But in 2017, style icon Kylie Jenner challenged the very foundation of a sweatshirt by wearing a cropped version of it — like really cropped. It was all sleeve, no body. Hardly anything remained of the original Harley Davidson logo on the front (via Teen Vogue). Fans were left super confused after Jenner shared an Instagram selfie sporting what was essentially a shrug paired with a ribbed tank top. Someone aptly called it a "sweatshirt necklace." 

Not long after the outfit debuted on social media, Cosmopolitan reported that Jenner stepped out of her house in that same barely-there sweatshirt. As rightly pointed out by HelloGiggles, it could inspire DIY projects for recycling old sweatshirts into Jenner fits. A snip here, a snip there — and you're all done.

Vogue reported that Jenner is somewhat of a trendsetter when it comes to the cropped sweatshirt. Everyone, from her supermodel sister Kendall Jenner and their supermodel friends Gigi and Bella Hadid have since been spotted wearing their own renditions of the fit.

When you're as prominent a personality as Kylie Jenner, there's really no escaping the eagle-eyed public that observes every step — and misstep — you take. In 2016, allegations surfaced that her Coachella Festiva outfit was a copycat. The young socialite had opted for a sequinned two-piece swimsuit from the brand Discount Universe and completed the look with pink and green braided hair (via Hello!). However, someone had apparently already pulled off a similar chic appearance, and just days before Jenner debuted her look. 

Teen Vogue reported that Australia-based social media influencer and designer Brit Day revealed the look two weeks before Jenner attended Coachella. Day marked her presence at the Rabbit Eats Lettuce festival in New South Wales donning the same eye-detail bikini that Jenner later wore. What's more, Day's hair was also dyed pink with her outfit — just like Jenner's.

Taking a good-humored approach toward the supposed twinning incident, Day shared a side-by-side image of both her own and Jenner's looks on Instagram, writing, "When the babe'n @kyliejenner steals your look!!" Speaking to outlet ZM, Day later said she was "flattered" about what happened. "There was no negativity intended in my post. I'm stoked that my girl crush supposedly has a crush on me!"