The Most Inappropriate Outfits Kendall Jenner Has Ever Worn

Kendall Jenner has often been deemed one of the most beautiful women in the world, which is probably one of the reasons she is subsequently one of the highest-paid models of all time (via Harper's Bazaar). She is perhaps best known for her super-chic style (and nail art almost as intricate as her sister Kylie's) that gives off an incredibly effortless yet expensive street-wear vibe. It's a style that has evolved along with Jenner as she has grown up in the public eye (via Vogue).

But as beautiful as she looks in glamorous clothes, Jenner manages to look just as beautiful in a sort of "naked" fashion that she has adopted over the years. Naked fashion, according to InStyle, is a style of "barely-there designs and expertly-placed material" that make the model appear nude, despite the presence of clothing. This look is pretty prominent within the Kardashian/Jenner family, the sisters challenging fashion norms by donning clothing that gives the illusion of nudity in a chic and high-fashion way. But Kendall Jenner appears to have run with this look even further, making it something of a fashion staple than an exception within her wardrobe. Here are some of the most naked — and borderline inappropriate — outfits that Jenner has proudly and publicly sported.

Jenner arrived at the 2017 Met Gala and managed to drop jaws more than she normally already does. This particular year, the show attempted to challenge attendees to "rethink fashion as a site of constant creation, recreation, and hybridity," by making the theme, "Rei Kawakubo/Comme des Garçons." Kawakubo has been deemed one of the most important and influential fashion designers of the past 40 years, "defining the aesthetics of our time," per Vogue. Kawakubo's work thrived on contract, with themes that celebrated "in-betweenness."

As for Jenner's interpretation of the assignment, she went with a La Perla Haute Couture naked dress that left very little to the imagination (particularly when she turned around). Despite the revealing nature of the dress, however, the dramatic draping, beautiful fabric, and shiny crystal details made it quite feminine and perfectly suited for the event (via Glamour). As Harper's Bazaar noted, you might have been able to see Jenner's diamond underwear through the gown, but her dress did come with 85,000 hand-placed crystals to take our attention off of her behind. 

When Kendall Jenner models naked outfits, she often goes for a subtle kind of look, many times playing on optical illusion by wearing flesh-toned fabrics, for example. But in 2018, she decided on a naked look that was incredibly on the nose. In May, Jenner attended an event during the Cannes Film Festival for the luxury watch and jewelry company Chopard, and her Christian Louboutin heels were the item of clothing that covered the most skin that night (via Fashionista). Yes, Jenner did think to pair her look with Chopard accessories (via Harper's Bazaar), but we seriously doubt anyone was staring at her ears. 

To the event, Jenner wore a seaweed-green, skin-tight one-piece outfit made from a dramatic, very see-through mesh material from Alexandre Vauthier, according to Marie Claire. While she appeared to pair the number with some nude-colored underwear, she opted to go sans-bra in a sort of chic, "Free the Nipple" inspired outfit. Of course, Jenner — who modeled in her first Victoria's Secret Fashion Show in 2015 (via Metro) — is used to baring it all. She regularly stomps down the runway in lingerie for all to see. And really, why shouldn't she?  

In September of 2020, Jenner made a jaw-dropping appearance at a Longchamp Spring/Summer fashion show at New York Fashion Week. While she sat next to Kate Moss, all eyes were on Jenner for a few reasons (via Harper's Bazaar). Her impeccably painted fire-hydrant red lips were only part of Jenner's allure that night. 

Longchamp, a French company that specializes predominantly in luxury leather goods, decided to introduce the world to their first-ever evening gown by requesting Jenner (their brand ambassador) to wear it. Indeed, she also grabbed the public's attention due to the revealing nature of the dress. Despite the dress technically covering her from shoulders all the way down to high heels, it is arguably more skin than fabric. Case in point? The gown features a dramatically long, plunging neckline accompanied by an opaque fabric and a velvet print of jockeys on horseback, the Longchamp logo (via Vogue). While the model did pair the dress with high-waisted briefs, in what seems to be Jenner's signature look, she opted to let the dress expose her nipples.