Kylie Jenner's Worst Social Media Pictures Posted Over the Years
Christopher Ramos
Updated on October 07, 2026
Kylie Jenner from The Kardashians gained her following through social media, but even the queen of Instagram has shared a few flop photos.
Kylie Jenner from The Kardashians gained her following through social media, but even the queen of Instagram has shared a few flop photos. Fans were first introduced to Kylie when she was nine-years-old on Keeping Up With The Kardashians. At the time, Kylie was just the little sister of Kim Kardashian, but she eventually became a force similar to her older sister.
Kylie was known for her popular Instagram posts, where she showed her fans everything from her makeup routine, favorite looks, and more. The now 24-year-olds obsession with social media became her career and helped her become the success she is today. Now Kylie is the founder of Kylie Cosmetics, which has since branched out into skincare, baby products, swimwear, and more.
Despite Kylie's success, she still makes mistakes on her social media. However, Kylie isn't the only one in the Kardashian-Jenner clan who has made a mistake or two online. Whether it's black-fishing or photoshop fails, Kylie has made a number of social media flops.
Kylie's Nightmare On Elm Street Collaboration
Back in October 2021, Kylie came out with a Nightmare on Elm Street collection for her makeup line. To announce the new collaboration, Kylie did a photoshoot of herself in a bedroom (similar to the one from the movie) with blood on her arm, Freddy Krueger's claw fingers, and his infamous green and red striped sweater. While Kylie looked amazing, fans were a bit freaked out by the Nightmare on Elm Street collaboration. Even though the collection was for Halloween, some fans didn't love the scary look.
Kylie Overly Filtered
One of the most talked about mishaps on the Kardashian-Jenner's social media is over-using filters. In a photo from January 2021, Kylie shared a series of snaps of herself with super face-tuned face and physique. While Kylie looks amazing, she looks different in every photo she takes.
Kylie's Photoshop Mishap
In a snap from July 2019, while on vacation in Turks and Caicos with her best friend Stassi, Kylie shared a photo of the pair that the fans couldn't help but make fun of. While the two friends look incredible, fans couldn't help but notice the photoshop mishap behind Kylie. The pillow she is leaning up against is clearly distorted as the stripes look more prominent on the right side compared to the left. While the Kardashian-Jenner sisters are known for their photoshop fails, this one was a surprise.
Even though The Kardashians star has had more than one social media photo flop, Kylie still manages to be one of the most followed on Instagram accounts. Kylie's worst photos even manage to get a least 1 million likes.
Next: Why Fans Think Kylie Jenner Hires Her Own Photographer
Source: Kylie Jenner/ Instagram