Kylie Jenner's Most Embarrassing Makeup Fails As A Beauty Mogul

Kylie Jenner's makeup skills are, without a doubt, next-level — but it took a lot of practice (and a handful of slip-ups) for her to reach this point. "The Kardashians" star had just turned 18 when she started her own makeup brand, Kylie Cosmetics, in 2014 and added "beauty mogul" to her growing list of titles: reality star, fashion designer, model, and billionaire (you won't believe how much money Jenner makes in a day). "My earliest makeup memory would be in sixth grade," Jenner told WSJ Style of how she discovered her passion for makeup. "I would wear a purple cut crease to class, and no one else was wearing any makeup. That would probably be the moment I knew this was for me." She knew she had mastered the skill when even her famous siblings started to turn to her for help. "When they started asking me to do makeup, that's probably when I knew," she added.

From her "King Kylie" era of 2014 (think teal hair, overdrawn brows, and big, overlined lips), Jenner has adopted a no-fuss and casual approach to beauty. These days, she's no longer a massive fan of bushy brows and lash extensions. "There are just certain trends that I've grown out of," Jenner stressed in a 2024 Elle interview. She's also sworn off thick and heavy foundations, noting to British Vogue, "I love letting my skin and freckles show."

But even with her expertise, it's not always that the Kye founder has her makeup game down pat. Like many other celebrities, she, too, has suffered her fair share of makeup mistakes over the years, some more embarrassing than others. 

In 2015, Kylie Jenner attended the star-studded "Seriously Popular" boat party hosted by the Daily Mail in Cannes, France. She arrived in a stunning sheer number by Francesco Scognamiglio alongside her momager, Kris Jenner, and then-boyfriend Tyga, who sported a matching ensemble (they dated from 2015 to 2017). However, it's hard not to notice Kylie's makeup with an excess of powder and contour around her face, giving her a slightly muddy, unnatural finish. Thankfully, her eye makeup and lip color — a gorgeous shade of nude pink — helped to balance her overall look.

Although it's unclear who did Kylie's makeup, her go-to makeup artist, Ariel Tejada, previously shared tips on how to avoid over-contouring in a 2015 interview with Allure. According to him, one of the most common reasons contour can look harsh is using a shade that's way too dark for your skin tone. To avoid this mistake, Tejada suggests choosing a color that is only slightly darker than your complexion. He also stressed to Teen Vogue that applying contour to the right areas of your face is key to achieving a snatched look.

"I feel like people mistake contouring for a cookie cutter method, thinking that you have to go around the hairline and the cheekbone," Ariel explained. However, this isn't always the case. For a softer, more natural look, choosing a powder bronzer over a cream contour is the way to go, he said. "A little soft bronzer underneath the cheekbone will really just enhance your features and make your cheekbones look a little more plump and high," the celebrity MUA added.

Unfortunately, Kylie Jenner's love of a nude lip hasn't always worked in her favor. In 2015, she attended Cosmopolitan magazine's 50th anniversary celebration wearing a shade of nude lipstick that didn't particularly suit her complexion. The color, a lifeless brown, looked lackluster on her lips and left her appearing washed out and even ill (shown above). She paired it with arched, sculpted eyebrows that have become her signature look, a soft glowing base, and smokey eyes. She also wore a platinum blonde wig.

When finding the ideal nude shade for your lips, CTZN Cosmetics co-founder Aleena Khan advises not to stray too far away from your natural lip color. As she told British Vogue, "The most popular industry definition for a nude lip is one shade above your natural lip tone; this is how you avoid looking washed-out and choosing a shade that is too pale for you." However, it's also worth noting your undertone — whether you're cool, warm, olive, or neutral. For cool undertones, like Jenner's, you should opt for a nude lipstick with a hint of pink instead of brown. Those with warm or olive undertones should look for nude shades with brown or mauve tones, while people with dark skin tend to look best in chocolate or deep-berry nudes. Don't be afraid to play around with different hues! "To find your true match, it's going to take some experimenting," Lupita Nyong'o's MUA Nick Barose explained to Teen Vogue. "Anyone can wear nude lipstick, you just have to find the shade that flatters your complexion."

Another makeup faux pas Kylie Jenner has suffered was having cakey foundation at the second Annual Diamond Ball in 2015. A close-up shot of her face showed her makeup to be more textured than it appeared in other photos, with creases under her eyes, dry patches, and cracks forming at the center of her lips. Eliano Bou Assi, Bobbi Brown's Director of Education and Artistry EMEA, said one common reason makeup tends to look cakey is using more face powder than is necessary. In an interview with Grazia, he said to only put powder on parts of your face that tend to oil up easily, adding, "Avoid powder on the dry parts of your face; otherwise your foundation will start to look cakey."

Over the years, Jenner has learned to ease up on her makeup and embrace a more natural approach to beauty. On Vogue's "Beauty Secrets" series in 2023, the Kylie Cosmetics founder demonstrated her updated makeup routine, saying, "My foundation just looks different. I feel way more natural. I like how it blends into my skin a lot better." Reflecting on her earlier Vogue episode, she admitted that she was shocked at the amount of makeup she used to put on her skin. These days, Jenner explained, "I wear a lot less [makeup], but I've accomplished the same snatched look." However, one thing that hasn't changed is her shopping habits when it comes to all things beauty. "I like to still buy tons of makeup online," Jenner confessed. "I just will always be makeup obsessed and I like seeing what's out there." 

There's no such thing as too much eyeliner and mascara — just ask 16-year-old Kylie Jenner. Seen here attending Avril Lavigne's Abbey Dawn Spring 2013 runway show, the future beauty mogul channeled her inner rockstar by wearing thick lashes and solid black liner around her eyes. She completed the look with thin eyebrows, muted pink blush, and glossy mauve lipstick to add softness to her face. Over time, Jenner's eye makeup style has changed from dramatic to much more subtle. "I'm really loving a tiny, baby wing [liner] just to bring out my eyes. ... I used to wear lash extensions for years, and then I stopped doing that," she shared in her 2023 Vogue "Beauty Secrets" episode. "I just wanted to really embrace my natural lash because I do have really good lashes," she noted, crediting her mother, Kris Jenner, for that.

Although mascara is still a part of her routine, Kylie no longer applies it heavily across her lashes. Instead, she focuses on just the outer corners to create an illusion of an almond shape, as she has naturally rounder eyes. In 2023, she even released her own mascara called the Kylash Volume Mascara, which she uses every day, along with her Kylie Cosmetics matte liquid eye shadow. As a makeup enthusiast, she knows how important eyelashes are to every look. "Eyelashes are everything — and I worked on Kylash for almost two years, making sure it performed and offered everything I look for in a mascara," Kylie told British Vogue. 

One of Kylie Jenner's tricks for making her lips seem bigger and fuller is over-lining them with a lip liner. And most of the time, it works — sometimes, it falls flat. At the launch party for Kylie Cosmetics' collab with Ulta Beauty in 2022, Jenner suffered yet another embarrassing makeup blunder by choosing a lip liner that didn't match her lip color. Sure, we get that it's part of her look, but the unblended line seemed harsh against her lipstick and, unfortunately, aged her a few years. More than just her lips, though, Jenner, seen here posing for a selfie with influencer Colt Paulsen, also went a bit too heavy on her contour and bronzer. At the very least, she could have toned down her base to keep the focus on just her cheeks and lips. 

Jenner's lips have always been a topic of conversation. In 2015, she finally admitted to getting temporary lip fillers in an episode of "Keeping Up With the Kardashians" after much speculation regarding her plastic surgery habits. She opened up about her decision to get her lips done on her E! series "Life of Kylie" years later, admitting it was rooted in her insecurities about her natural puckers. "I just didn't feel desirable or pretty," she admitted (via W Magazine). "I really wanted bigger lips. I would overline my lips with lip liner just to create the illusion of bigger lips. And then finally I was like, this lip liner isn't doing it."