Kylie Jenner's Inappropriate Outfits Have Left Us Speechless

There are child stars and then there's Kylie Jenner, whose name has been known the world over since she was a grade-schooler, thanks to her famous family allowing the cameras in for their series "Keeping Up with the Kardashians." In those early days, Kylie and her slightly older sister, Kendall Jenner, were the cute kiddies playing second fiddle to older siblings Kim, Khloé, and Kourtney Kardashian. Fast-forward a couple of decades, though, and Kylie has become a force of nature in her own right and a veritable fashion icon. Thanks to her Kylie Cosmetics line, Kylie reportedly became the world's youngest-ever self-made billionaire, according to Forbes, crossing the threshold at the tender age of 21 back in 2019. More recently, she launched her own clothing line in Khy.

All the while, the youngest member of the Kardashian-Jenner sisterhood has made headlines and won fans from every corner of the globe with her own, unique style. Be it through her ever-evolving array of red-carpet looks or the snaps posted on her ridiculously popular Instagram account, Kylie has cemented herself as a trendsetter in every sense of the word. Even as Kylie has positioned herself as the person to follow for those wondering what to wear, though, she has occasionally found herself making the wrong kind of waves with her occasionally controversial fashion moments. Some of them have even been branded inappropriate by observers. Here are some of the looks that left people speechless for being a bit too much.

Where celebrity weddings are concerned, the joining of Amazon founder Jeff Bezos and former journalist Lauren Sánchez in Venice was the ceremony of 2025; a gathering that drew the elite of the elite — people like Oprah Winfrey, Bill Gates, Tom Brady, Sydney Sweeney, Leonardo DiCaprio, et al. Naturally, it's a crowd that also included the Kardashian-Jenner crew. As one might expect, Kylie Jenner went all out to cultivate a look that would get people talking, sporting a dress that featured a corset bodice, spaghetti straps, black bows, and a plunging neckline. And while the frock may have drawn raves in another setting, Jenner caught a significant amount of criticism for wearing it due to its violation of an age-old wedding rule.

"While fashion icons flocked to Venice, one outfit stole the spotlight for all the wrong reasons," influencer Mario Nawfal commented, via the Daily Beast. "Ivanka Trump and Oprah Winfrey were among the A-listers turning heads at Jeff Bezos and Lauren Sánchez's star-studded ceremony. Then, Kylie Jenner showed up in a white, form-fitting dress ... breaking the number one rule of wedding guest etiquette." Commented one fan, via X, "Just tacky. You shouldn't wear anything white or close to white on someone else's day."

In many respects, Kylie Jenner's meteoric rise to the absolute upper echelon of celebrity is unprecedented. By the time she could officially order her first adult beverage, she was already one of the wealthiest people ever to walk the earth, as well as one of the 10 most-followed people on Instagram, having racked up more than 100 million followers by 2018, a number that has more than tripled since then. Given the number of eyeballs marking her every move, the clothes she wears have been subject to public dissection from a very young age. And, at times, those outfits haven't been age-appropriate in the eyes of some pundits. 

In March 2015, when Jenner was just 17, people were taken aback by her revealing looks at a London event and a photo shoot a few days later. Appearing at a soiree for the cosmetic brand NIP+FAB at Vue Westfield, Jenner spurned convention by wearing a sheer top that did little to conceal her skin and the black push-up bra beneath it, as reported by the Daily Mail. The same outlet published photos of her again within the same week, showing her in a cut-out swimsuit during a Los Angeles shoot. "Why must she grow up so fast? When I was 17, I was still in high school and just being a normal, well-grounded teenager. Really sad," commented one reader.

Whether you're talking about the events in New York City, London, Milan, or Paris, Fashion Week is like the Super Bowl or the Kentucky Derby in the world of celebrity style, and Kylie Jenner is often at the center of the pomp and circumstance. However, not all of her looks have landed with fans and critics. Such was the case in September 2016 when she was attending the Spring 2017 Jonathan Simkhai Fashion Week show in New York in a denim jacket and jeans with a white durag to cap off the look. It was an ensemble that invited criticism because of the durag in particular, with some opining that it represented an appropriation of Black culture, while others simply thought it was tacky.

"Kylie Jenner wearing a durag is my last straw. Cancelled and deleted. Next," one observer quipped, via X. "#NeverForget when Kylie Jenner wore the most unnecessary durag of all time," another X user commented. As reported by various outlets, this wasn't the first time Jenner had been accused of cultural appropriation; she had also been spotted rocking cornrows and a Yaki ponytail on previous occasions.

The durag incident wasn't the first time Kylie Jenner was accused of wearing an outfit that some people considered to be racially insensitive. In October 2015, during the peak of the Halloween season, Jenner took to Instagram to share a video of herself in what she strangely dubbed her "Eskimo" costume. Of course, that term is an exonym ascribed by nonnative people to the native Inuit and Yupik people of Canada, Alaska, and parts of Russia, considered by many to be a racial slur. Her use of the word turned what otherwise might have been a crowd-pleasing outfit into a bona fide controversy. Jenner seemingly realized the error of her ways, too, referring to herself instead as the "Snow Princess" in a subsequent Instagram post.

By that point, though, the damage was done. "'Eskimo Look??' I'm from northern Canada and have spent a good portion of my life with First Nations and Inuit peoples, and I can assure you they do not dress like this. This is cultural appropriation of the worst kind because not only is it offensive, it also sexualizes women of this culture. Please, Kylie, I am sure your parents raised you better. Take the picture down and show some respect," a Facebook user later wrote of the outfit and its description.

The interconnectedness between celebrities and the perpetually changing avenues thereof is probably as discussed in fandoms and on social media as what they're snapped wearing out in public. The evolving dynamics between Kylie Jenner and Jordyn Woods, or Kendall Jenner and Hailey Bieber, are evidence of the phenomenon. Sometimes, though, coverage of these celebrity friendships and the fashion faux pas of those involved intersect in moments of tabloid glory. Such was the case in early 2024 when the Jenner sisters and Bieber ditched the winter doldrums to vacation in a tropical locale.

Amid the fun and the frolicking, Kylie saw fit to share a video of their adventures via TikTok. However, the see-through lace skirt she wore was particularly revealing, lending glimpses of the younger Jenner sister's unmentionables. Still, fans of the number can apparently pick up their very own — the Saint Midi Skirt from With Jéan was available online at the time of publication for just $142.

If anything can be said about Kylie Jenner amid her evolution from a "Keeping Up with the Kardashians" backup player to a fashion mogul global icon in her own right, it's that she's not afraid to take a risk, and that sentiment goes double for her trendsetting duds. However, she may have bitten off more than she could chew in January 2023 when she appeared at Schiaparelli's Spring-Summer 2023 show during Paris Fashion Week wearing a black gown from the fashion house that also featured a questionable piece of faux taxidermy. Specifically, Jenner's dress was capped off with an incredibly lifelike lion's head as its centerpiece; a look that was also featured in the runway show itself.

Although Schiaparelli insisted the bust — and others like it that were also featured during the show — was fake and offered an explanation for it, Jenner and the famous designer were nonetheless criticized for condoning and even promoting trophy hunting with their wild looks. "Although they stated it is faux, how could they possibly think this is fashion? This sends the wrong message & fuels not only the exotic fur trade, but #trophyhunting!" read a post from one animal-centric X account.

Sometimes, when criticism is levied at a celebrity for wearing a particular outfit or accessory, the outrage is sparked as much by the person as the look itself. People who are as visible and interwoven in the public discourse as Kylie Jenner are simply going to elicit large, emotional reactions from the masses, regardless of whether their actions actually warrant the attention. In this particular case, though, there were already big feelings about whether the accessory in question was appropriate attire for, well, any person or situation; never mind the Jenner of it all.

During a Paris Fashion Week event in 2023, Jenner was snapped wearing a controversial noose-like necklace from Givenchy. The necklace made its debut at Givenchy's Spring/Summer 2022 collection in October 2021, and it immediately drew criticism for its potentially nefarious connotations. "You'd think the industry would've learned not to put things that resemble nooses around a model's neck after the whole @Burberry noose hoodie debacle in 2019," commented a prominent, fashion-forward Instagram account at the time. Meanwhile, commenters on the platform were quick to criticize Jenner for bringing the look back into the public consciousness, with one writing, "First a lion head now a noose around your neck, with your platform, should you be even wearing these items?"

The Schiaparelli incident wasn't the first time that Kylie Jenner has landed herself in hot water with animal rights activists and fans alike; her penchant for including fur — real or fake — in her ensembles has similarly drawn the ire of those who are sensitive to the problematic nature of overtly animal-based fashion. In December 2019, Jenner fanned the flames with an Instagram post showing her and gal pal Stassie Karanikolaou wearing coats that are known to be made with real fox fur. Jenner and Karanikolaou have worn tandem costumes before, but their matching fur coats may have been their most infamous effort to date. Elle reported that the duo appeared to be wearing "Foxy Gloss Coats" by Saks Potts, which have collars and cuffs made from real fox fur.

The backlash to the coats was swift and less than positive in many instances. "Poor Animals, so sad," wrote one Instagram commenter, who further referred to Jenner as a "killer." Meanwhile, another Instagram comment to Jenner's post read, "Omg I just want to throw up. How can you use fox skin??? Do you know how they take it? The fox is still alive while they are cutting his skin off." Despite the tepid response, Jenner has continued to incorporate fur into her fits. In 2025, she released a series of faux fur coats through her Khy clothing line.

Given the celebrity world she was born into, the incredible attention that was afforded her as a teen, and her jet-setting lifestyle, it can be difficult to think of Jenner as a mother actively raising children. That's exactly what she is, though, having welcomed both a daughter, Stormi Webster, and a son, Aire Webster, into the world via her relationship with rapper Travis Scott. As such, Jenner must work her various headline-grabbing exploits around her primary role as a mom of two. That includes making sure her brood gets home safely from school and, apparently, Jenner has no qualms about rolling up in the proverbial minivan in an outfit that may be better suited for the dance floor.

During a March 2025 video posted to her socials, including Instagram, to promote her clothing line, Khy, Jenner quipped that she would pick up her kids in the form-fitting latex frock she was wearing in the clip. In addition to accentuating her sinuous figure, the shiny red dress she wore featured a plunging neckline sure to make even the most stalwart clubgoers blush. Jenner also claimed she would wear the number to a business meeting. Wrote one commenter in response to the fit, via Instagram, "Really? Kids school? Are you okay?"

While Kylie Jenner is a veritable force where getting attention and generating press are concerned, the reality star's comings and goings alongside her Oscar- and Golden Globe-nominated beau, Timothée Chalamet, are a beat unto themselves. To that end, the couple gave its audience something to talk about in a major way when Jenner accompanied Chalamet to the 2025 Oscars in a black dress that trended for all the wrong reasons. As is her wont, Jenner was wearing a custom Miu Miu bustier dress with a particularly noticeable cut-out detailing; an ensemble that stood in stark contrast to Chalamet's yellow suit from Tom Ford, and one that ended up being the talk of the Tinseltown fashionistas.

Joked one observer about the pair, via X, "They're there promoting their next film: 'Elvira, Mistress of the Dark, Hooks Up with Banana Dracula.'" "I've seen porn stars dress more modestly," wrote another commenter on the same platform. There may be an outfit for every situation, but this wasn't it in the eyes of many.

Kylie Jenner causing a ruckus with her award show fashion isn't a phenomenon confined solely to the Academy Awards. The low-cut, vintage Atelier Versace gown she wore to the 2025 Golden Globes also managed to raise eyebrows due to the way it revealed and even emphasized her cleavage. Apparently, the dress was so revealing that even Jenner, whose socials are flush with snaps depicting her half-clothed or less, was unsure about whether she should have worn it to the event. However, she was reassured about the decision after the fact by her mother, Kris Jenner, as chronicled in "The Kardashians."

On the Season 6 finale of the Hulu show, a phone call between the two was captured by the camera, during which Kylie contended with her call to leave so little to the imagination. Said Kris, in response to her youngest daughter's concerns, via Entertainment Tonight: "Yes. You have to wear your best dress to every function you go to. No matter what."

In a world where the necklines on her dresses are almost always nonexistent (or close to it), the plunging, corseted number Kylie Jenner wore to the Jean Paul Gaultier fashion show during Paris Couture Week in January 2025 still managed to make waves. Jenner shared several pictures of herself in the bronze-colored gown via Instagram, inviting commentary both positive and negative from the peanut gallery. "Respect your body and yourself," pleaded one commenter on the platform. "Why can't you girls dress classy??? This is terrible," opined a second Instagram user, while a third wrote, "Ur going to be so sorry down the line sweetheart u really are get help now."

Jenner's dress was created by one of the Kardashian-Jenner crew's go-to designers, Ludovic de Saint Sernin. And Jenner has rarely been the one to dress conservatively at these kinds of events. So, chances are we'll be seeing more of moving forward.