Kylie Jenner's Most Controversial Fashion Moments

Kylie Jenner became the face of lip fillers when she fessed up to enhancing her pout on "Keeping Up With the Kardashians," and the change paid off. Her new canvas allowed her to show off more lip color than before, and she made a killing selling her Kylie Cosmetics lip kits. But Jenner is more than just a famous face; she's a seasoned pro at making headlines for what's going on below her neckline, dressing in top-tier designs from the likes of Balmain and Versace. Thanks to her robust Instagram following, she can also show off her style and start trends whenever she pleases.

When CR profiled the makeup mogul, the magazine styled her in a top that captures the essence of Jenner: a one-of-a-kind custom piece constructed out of containers of her lip gloss. With an estimated wealth of $750 million as of January 2023, per Celebrity Net Worth, Jenner can stuff her closet with pretty much any custom pieces she pleases, and she told CR that she's saving her entire wardrobe to pass down to her daughter, Stormi Webster. "Hopefully she wears one of my Met dresses to prom," said Jenner. Stormi already owns a mini replica of one of her mom's Met Gala looks, which Jenner dressed her in for Halloween in 2019. "How narcissistic can you be," read one tweet about the costume. Some of Jenner's other style decisions have similarly earned her critics' disapproval, keeping the lip kit queen's name on their lips.

Showing up to an event wearing the exact same outfit as someone else can be pretty awkward, but when it happened to Kylie Jenner, it caused a huge internet uproar. As Jenner sat in the front row at Schiaparelli's SS23 couture runway show during Paris Fashion Week, model Irina Shayk strolled right by her wearing an identical black gown with a huge fake lion's head affixed to the front. Social media users had a field day roasting Jenner over the surreal style moment. "2ND HAND EMBARRASSMENT: Kylie Jenner's 'Lion, Witch and the Wardrobe' look stolen mid-fashion show. Fashion moves so fast," quipped one Twitter user.

More Narnia jokes about Aslan meeting a cruel fate flooded Twitter, but some critics didn't view the ultra-realistic animal heads that Schiaparelli used on its looks as a laughing matter. Per British Vogue, other models wore fake foam wolf and snow leopard heads, additions that had animal rights supporters accusing Schiaparelli of promoting big game hunting and glamorizing the use of real animal products in fashion. "The craftsmanship to create faux taxidermy while honoring trophy killing in a time where every single one of these animals are endangered species is obscene," tweeted designer/activist Céline Semaan.

However, PETA president Ingrid Newkirk voiced her approval of the designs, which were a nod to Dante's "Inferno." She told TMZ, "These fabulously innovative three-dimensional animal heads show that where there's a will, there's a way."

One of the most divisive style decisions a celebrity can make is to wear apparel made from real fur instead of opting to go faux, and Kylie Jenner has chosen the former route on more than one occasion. In 2019, Jenner and her bestie, Stassie Karanikolaou, posed for an Instagram photo wearing coats in cartoonish shades of blue and orange. According to Cosmopolitan, the garments looked like Saks Potts designs, which would mean that they were trimmed with real fox fur. "Animal Abusers. Would you like being skinned alive? If the answer is no, then why do you do it to the innocent animals????!!!!" read one response to the photo. "This is not fashion; this is animal cruelty," another person commented. Others joked that the friends' color choices made them look like "Dumb & Dumber" characters Harry and Lloyd.

Jenner angered animal lovers again in 2020 when she claimed to care about her furry friends, sharing a post on her Instagram Story lamenting the deaths of millions of animals in wildfires ravaging Australia. Per Us Weekly, she modeled a pair of $1,480 Louis Vuitton slippers covered with mink fur mere hours later, prompting critics to accuse her of blatant hypocrisy. "Kylie posting her mink fur sandals right after her koalas dying post is peak fake woke behavior," one Twitter user wrote. Per People, Jenner responded to the controversy by making a $1 million donation to aid wildfire relief in Australia.

Kylie Jenner and Kendall Jenner share a passion for fashion, so it seemed like a no-brainer for the sisters to create their own clothing line. In a 2015 interview with Teen Vogue, Kylie said of their apparel, "We're taking in a lot of different inspirations these days from the fashion world, but our California aesthetic will always be represented." However, some fans weren't feeling the "California Love" when the siblings decided to incorporate images of the late rapper Tupac Shakur into their Kendall + Kylie designs. In a move that outraged and confounded critics, they released a collection of T-shirts with their own likenesses printed over those of various musicians. One shirt's superimposed image inexplicably featured an Instagram snapshot of Kylie posing on the edge of a pool and a shirtless Tupac photo, per Harper's Bazaar. Kendall's face covered pictures of Tupac and The Notorious B.I.G. on another tee, prompting one Twitter critic to write, "Tupac and Biggie did not f***ing die to be printed on a shirt with Kendall and Kylie."

Kylie tweeted an apology that read in part, "We are huge fans of their music, and it was not our intention to disrespect these cultural icons," but this didn't save the Jenners from being sued by the photographer who took the pics of Pac. Per TMZ, the lawsuit was settled out of court, so if the mistake resulted in monetary compensation, the amount was never disclosed.

In 2019, Kylie Jenner scored an invite to Hailey Bieber and Justin Bieber's wedding. Hailey enlisted Off-White founder Virgil Abloh to design her romantic lace wedding gown, which featured a dramatic train, long sleeves, and an off-the-shoulder neckline. The model's Instagram followers were obsessed with the dress, with one admirer describing Hailey as "the most beautiful bride ever." However, some fashion fans felt that Jenner tried to upstage Hailey's dreamy bridal look by rocking a sexy one-shoulder gown in gold. It was a J'Aton Couture design that featured a revealing cutout on the bodice and a wide front slit that bared most of her thighs. Per Page Six, Jenner paired it with slinky gold Stuart Weitzman sandals and carried a bejeweled Judith Leiber Couture handbag shaped like a butterfly.

The fashion police came out in full force, not because they thought the gown looked bad but because Jenner was a stone-cold glamazon. "Show up to my wedding looking like Kylie Jenner at Hailey & Justin Bieber's wedding, and you will be escorted out lol," one Twitter user quipped. Others suggested ways for Hailey to get revenge on Kylie for stealing some of her shine on her big day. "Hailey has to give birth at Kylie's wedding because I wouldn't take that," another person wrote. But there were also those who weren't as impressed with the crinkly, shiny gown. "Kylie looked like a Ferrero Rocher," one critic opined.

When Kylie Jenner hit the red carpet at the 2022 Met Gala, she looked like she was ready to get hitched and hit the ballpark. That year, attendees were asked to dress in "gilded glamour and white tie," per InStyle. While it seemed like a more suitable occasion for the gold gown that she wore to Hailey Bieber's wedding, Jenner rocked a white wedding dress instead. It was a frilly confection with a ruffled skirt and a T-shirt-style mesh top fused with a more traditional sweetheart bodice. On her head, Jenner wore a backward baseball cap with a fishnet veil. The look perplexed many Twitter users. "Kylie Jenner's Met look is exactly what I imagine they would have the star of a Disney Channel Original Movie wear to a fictional Disney universe Met Gala," one person wrote. "No matter how hard I try, I can't erase Kylie Jenner's snapback & wedding dress combo from my mind. If there is a God, please release me from the shackles of this curse," tweeted another distressed critic.

On Instagram, Jenner explained that her outfit was a homage to Off-White CEO Virgil Abloh, who died in 2021, per People. "I'm humbled to wear this dress and honor my talented, beautiful friend," Jenner wrote. This crucial detail made some netizens warm to the look, but one savage tweet read, "Kylie honey ... Virgil would've told you to wear something else."

In February 2017, Kylie Jenner began offering black sweatsuits featuring flame graphics at one of her pop-up shops in NYC, and the apparel looked familiar to some fashion fans. As reported by Seventeen, an independent label, Cake Asia, was already selling similar sweats. Jenner even used the same musician model as Cake Asia did in her promotional campaign: Offset.

Seventeen did pour some water on the flame controversy by sharing images of comparable designs from other brands, making it difficult to discern who, if anyone, was getting ripped off. However, Jenner found herself under fire again a few months later.

This time, she added some merch to her online store that possibly looked familiar to Destiny's Child fans: colorful camouflage crop tops, bikinis, and pants. According to Complex, the indie apparel company PluggedNYC released a similar collection first. Two brands using a popular pattern like camo could easily be viewed as a coincidence, but the designer who created PluggedNYC's pieces, Tizita Balemlay, had receipts: email evidence proving that Jenner had purchased garments from PluggedNYC before dropping the similar looks. On Instagram, Balemlay alerted customers about the potential theft and released a statement to Complex that said in part, "Money is power, and the Kardashians have both ... At the end of the day, this will be all blown over tomorrow, her sales will continue." However, some social media users did call Jenner out, with one person tweeting, "She is a culture vulture."

In 2017, Kylie Jenner was ruthlessly mocked after modeling an unusual top on Instagram. It was a Harley-Davidson sweatshirt, but most of the branding was gone; it was cropped at the armpits, and the jagged hem made it look as though it got caught in the wheel of a Harley and yanked back out. Lest you call Jenner a poser for paying homage to a brand beloved by biker gangs, she has actually sat astride a motorcycle before. In 2017, she rocked pink lingerie while posing on a color-coordinated bike, and she even rode a motorcycle on "Life of Kylie" that same year, per E!.

While Jenner was clearly going through a phase of fascination with the fast machines, fans just didn't get her hacked-off Harley sweat top. "Someone ate her shirt," a Twitter user wrote. "When you don't know if its gonna be hot or cold," quipped one of Jenner's Instagram followers. "Wth is she wearing?! Is that a loin cloth around her neck or a scarf?" another person asked. Jenner paired the shirt with a tank and distressed jeans that also looked like they'd been through the wringer; the huge holes on the thighs exposed the lining of her pockets.

According to Teen Vogue, the top was designed by Sami Miró Vintage, a brand that upcycles old pieces to create eco-friendly looks, per Models.com. So Jenner was just doing her part to help the environment by wearing a sweatshirt as a necklace.

When Kylie Jenner was profiled by Interview magazine in 2015, the then-18-year-old promoted her anti-bullying campaign. She also spoke about the darker side of fame, saying that she's so fearful of being viewed in a bad light that the first thing she does upon awakening is to check the internet for any negative headlines that mention her name. After Interview published its piece, she lived her worst nightmare; she got lambasted for agreeing to pose in a gold wheelchair for her cover photo.

People who actually use wheelchairs for mobility, not as accessories, were outraged. A critic with cerebral palsy, Erin Tatum, recreated the photo on Tumblr and shared her thoughts about Jenner's Interview cover in her own interview with Self. "It's absurd that real-life disabled people get hardly any attention or recognition, but celebrities feel entitled to appropriate disability as some kind of artistic statement," she said. "You almost never see disabled models." Twitter users also scolded Jenner for being ableist, tone-deaf, and insensitive. "If Kylie Jenner thinks a wheelchair is a fashion accessory, she can have mine, and the crippled up painful body that comes with it," one person wrote.

In response to the backlash, Interview didn't apologize, but issued a statement to E! that said in part, "Our intention was to create a powerful set of pictures that get people thinking about image and creative expression." The publication certainly succeeded in getting people to think about Jenner's image.

Rihanna and Kylie Jenner have a lot in common. They've both launched successful makeup brands — Fenty Beauty and Kylie Cosmetics — and they both have massive Instagram followings. (However, Jenner is beating Bad Girl RiRi in that arena by over 200 million followers at the time of this writing.) If E! is to be believed, they've also both dated rapper Travis Scott. But for some Rihanna fans, the style similarities between the singer and Jenner are a little suspect. In 2019, Page Six tweeted a photo of the women wearing the same leopard-print LaQuan Smith catsuit. RiRi wore it first during an Interview magazine photoshoot, and Jenner followed suit a month later, showing hers off in a shadowy mirror selfie. In response to Page Six's tweet, one fan shared other examples of Jenner purportedly stealing RiRi's style. Another person wrote, "The tweet headline is inaccurate lemme help y'all out ... 'Kylie Jenner's obsession with copying EVERYTHING Rihanna does continues.'"

Per Refinery29, two different designers who crafted strikingly similar fringe jumpsuits worn by RiRi then Jenner even got embroiled in a legal battle in 2017. Five years later, Vogue suggested that the sartorial nodding was still going on, sharing photos of Rihanna and Jenner rocking black leather coats over gossamer lace dresses. But who can blame Jenner for wanting to be like Rihanna? Per Forbes, the performer's beauty brand began outselling Kylie Cosmetics in 2018, helping her achieve billionaire status.

During Paris Fashion Week in 2023, Kylie Jenner styled a figure-hugging, electric blue Givenchy dress in a manner that caused controversy for more than one reason. According to Bustle, her glittery pink Shark Lock boots were also a Givenchy design. Some critics weren't fans of the footwear, which resembled the bottom of a pair of flared pants over pointy-toed shoes. "I feel like those are shoes Hannah Montana would wear," one of her Instagram followers wrote. Others, however, blamed one of her accessories for spoiling her look: a silver Givenchy necklace designed to look like a noose. "It's the fact that her necklace is a noose, come on! I know someone on her team had to have noticed that! #NotCool," read one comment. "You have biracial kids and wearing a noose around your neck?? Smh how embarrassing," another person wrote.

By the time Jenner wore the problematic cuff necklace, it had already generated a great deal of outrage. After the accessory made its runway debut at Paris Fashion Week in 2021, critics pointed out that the noose isn't just a symbol of hate due to its use in the lynchings of Black Americans; it can also be triggering for those whose lives have been impacted by suicide. When The Guardian reached out to Givenchy for comment, the label would not explain or defend the noose design, saying instead, "The house do not have an official response on this."

In 2019, Kylie Jenner threw a birthday bash for her close friend Stassie Karanikolaou and chose a theme that caused outrage. Jenner and her guests dressed in blood-red robes and white bonnets like those worn on the Hulu series "The Handmaid's Tale," which is based on Margaret Atwood's dystopian novel of the same name. The characters who wear the red habits are handmaids, women who are enslaved, raped, and forced to give birth. On her Instagram Story (via Hollywood Life), Jenner explained her theme choice by saying, "'The Handmaid's Tale' is my favorite show ever."

The handmaid costumes have become associated with resistance to laws that oppress women, thanks to the protesters who wear them as a stark warning about what can happen when women's rights are stripped away. But an actor who appears on the show, Bradley Whitford, didn't believe that Jenner was trying to make a meaningful statement. "It seems a little tacky ... A cocktail party seems to sort of dash all that significance," he said on "The Talk" (via ET). Twitter users also had thoughts about Jenner's little get-together in Gilead. "Nothing says 'fun' like dressing up as women who are habitually raped and denied basic human rights," one critic wrote. "She could be giving to organizations that prevent oppression, help the 1 in 3 women globally experiencing domestic abuse, but nahh let's have a party and make a theme out of their pain," another tweeted.

In October 2022, Kylie Jenner attended Acne Studio's SS23 fashion show in Paris, wearing a dress designed by the label that hadn't hit the runway yet. Per W magazine, she took her front-row seat and watched a model glide down the runway, rocking the same dramatic white gown. Jenner helped demonstrate the dress' versatility by styling hers with a pair of spiked earrings for a punk-rock vibe, whereas the model went for an earthier, goddess-like aesthetic by wearing a pair of cowrie shell earrings that trailed all the way down to her thighs.

The floor-length garment hugged Jenner's curves, and when she posed with her arms down, it almost appeared as though a long cape was draped over her back. However, she gave her Instagram followers a better look at exactly how the dress was designed by sticking her arms out to the sides and placing her hands on the walls of a hallway. This revealed that the loose folds of fabric were attached to the gown's sides and long sleeves, making her resemble a sugar glider in flight. To many of her Instagram followers, the look was giving bedsheet. "Me putting on my fitted sheet," quipped one commenter. "Feel like I could make this look with my bedding today," read another message. Others joked that Jenner was engaging in a little culinary cosplay, with one saucy comedian suggesting that she looked "Like a lil ravioli."

For her 2015 Halloween costume, Kylie Jenner wore a white crop top with a fur-trimmed hood, a matching miniskirt, and a pair of furry boots. On Instagram, she revealed that the outfit was her attempt at dressing like an "Eskimo," a word that is considered a slur by many people living in the Arctic. NPR has published an in-depth explainer on why the word is problematic, and the gist of the issue is that it was commonly used by racist colonizers who viewed the native inhabitants of Arctic areas as dangerous heathens.

According to HuffPost, Jenner changed the caption of one Instagram post to describe her costume as a "Snow Princess" instead, so she evidently noticed that she was getting called out over her ill-thought-out Halloween look. However, she did not remove the word "Eskimo" from a video showing off her glittery eye makeup, and she used the offensive exonym again in a 2016 Facebook post, revealing that the Halloween costume had been added to the "Kendall and Kylie" mobile game. In the comments, one of her followers replied, "I'm Inuit, 'Eskimo' is a derogatory term to us (not all), but we do not dress like that unless we want to be found dead in a snow bank. Please don't dress like us as a f***ing Halloween costume." Another person wrote, "This is cultural appropriation of the worse kind because not only is it offensive, it also sexualizes women of this culture."

In 2022, Kylie Jenner took to Instagram to show off an outfit that probably had more than a few of her followers doing a doubletake. At first glance, it was just a bubblegum-pink, long-sleeved top paired with a black miniskirt. But upon closer inspection, it appeared that two pairs of hands were grabbing her torso and hips.

According to E!, the garments with attached gloves were vintage 2007 Comme des Garçons pieces. When creative director Rei Kawakubo sent the looks down the runway, she told Vogue, "I'm tired of mundane, everyday fashion. I'm curious. I want something that takes us to another world." But Jenner wasn't journeying through the looking glass to Wonderland when she rocked the surreal outfit; she was visiting London with her daughter, Stormi Webster.

Some of Jenner's Instagram followers were a bit freaked out by her handsy ensemble. "Does anyone think the dress is creepy? It's soooo creepy imo," one person opined. "Like everything about you, Kylie, but this dress made me nervous," another message read. Then there were those who didn't seem interested in getting their hands on the outfit because it wasn't fashionable enough for their tastes. "This looks cheap and tacky for a woman of her wealth," sniffed a third commenter. If Jenner ever wants to block the haters out by covering her eyes and ears, those extra hands will surely come in handy.

In December 2022, Kylie Jenner shared an early Christmas gift with her fans: an Instagram photo that was just too easy for them to roast (like chestnuts on open fire). According to Page Six, Jenner was rocking a sparkly, multicolored outfit designed by Y/Project. It included a slinky, long-sleeved maxi dress and coordinating balaclava. Jenner modeled her unusual ensemble by striking a pose on a bed. "Waiting for Santa like ..." her caption read. But some wise-cracking fashion critics thought that she looked better prepared for Halloween.

"What in the sleep paralysis demon," quipped one Redditor. "I guess I'm too poor to understand ... fashion." Another person wrote, "It's giving ghostly apparition on paranormal investigation thermal camera." There was also a suggestion that Jenner was taking a page from Halloween queen Heidi Klum by rocking her own more colorful take on a worm — or perhaps the influencer was just getting desperate for cash. "When you have a bank robbery at three and a Balenciaga shoot at five," another comment read. 

While speaking to Marie Claire about her status as a trendsetter, Jenner once boasted, "I just do whatever I want to do, and people will follow." But does she wield enough power to get any significant number of her fans to start dressing like the Predator's doomed prey or a temperature map ninja?