Sophia Michaels
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Kylie Jenner’s makeup artistry is impressive, but it took significant practice, along with a few mishaps, to get to where she is today. She launched her makeup line, Kylie Cosmetics, at just 18, adding to her impressive resume that includes reality star, fashion designer, model, and billionaire—a fact that will surprise many regarding her daily earnings. Reflecting on her journey, Kylie recalled, “My earliest makeup memory was in sixth grade” while wearing a bold purple cut crease at school when most of her peers didn’t use makeup. It was a defining moment in realizing her passion. She knew she had grown skilled when her sisters began seeking her for makeup advice.
Since her “King Kylie” phase in 2014, characterized by bold teal hair and dramatic makeup, Kylie has shifted to a more casual beauty style. She now prefers natural brows and skin that showcases her freckles rather than heavy products. In a 2024 Elle interview, she mentioned, “There are just certain trends that I’ve grown out of.” Despite her expertise, she has experienced makeup fails that serve as reminders of the learning curve in beauty.
Disastrous Contouring in Cannes
At the “Seriously Popular” boat party in Cannes in 2015, Kylie made a fashion statement but faced criticism for her makeup. Accompanied by her mother and then-boyfriend Tyga, she wore a sheer gown by Francesco Scognamiglio. However, her contouring appeared excessive, leading to an unnatural appearance. Fortunately, she balanced this with beautiful eye makeup and a lovely nude pink lip.
While it’s unclear who applied her makeup, her primary artist, Ariel Tejada, provided contouring tips in a previous Allure interview. He pointed out that often, contouring mistakes happen when the shade is too dark for one’s skin tone. Tejada advises using a slightly darker shade and applying it strategically.
Ariel emphasized, “People often think contouring is a one-size-fits-all method.” For a more natural finish, he recommends powder bronzer instead of creamy products, stating, “A light bronzer under the cheekbone can help accentuate your features.” This technique enhances the cheeks without looking overdone.
Dull Lip Color Misstep
In 2015, at Cosmopolitan’s 50th anniversary event, Jenner’s choice of a nude lip color didn’t complement her skin tone. She opted for a dull brown that left her looking washed out and unwell. This look was matched with her trademark sculpted brows, a radiant base, and smoky eyes, along with a striking platinum blonde wig.
To choose the right nude lip color, Aleena Khan, co-founder of CTZN Cosmetics, suggests picking a shade close to your natural lip tint. She shared with British Vogue, “A universally flattering nude lip is usually a shade or two darker than your natural lips to avoid a washed-out look.” It’s also essential to consider your undertone—warm, cool, olive, or neutral—when selecting lip colors.
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Kylie Jenner’s Makeup Missteps Over the Years
Choosing the Right Nude Lipstick
If you have cool undertones, similar to Jenner’s, aim for a nude lipstick that carries a touch of pink instead of brown. Conversely, those with warm or olive undertones should lean towards shades that have brown or mauve hues. People with darker skin often find that chocolate or deep-berry nudes are the most flattering. Remember, discovering your perfect shade may require some experimentation. As Nick Barose, an expert makeup artist for Lupita Nyong’o, mentioned, “Anyone can wear nude lipstick; it’s about finding the tone that complements your skin.”
Makeup Mishap at the Diamond Ball
During the 2015 Diamond Ball, Kylie Jenner faced a makeup mishap characterized by excessive foundation that appeared cakey. A zoomed-in shot of her face revealed creases and dry patches, especially around her lips. Eliano Bou Assi from Bobbi Brown noted that this can happen if too much face powder is applied. He advised on using powder sparingly and only in oily areas of the face to avoid a cakey finish.
Over time, Jenner has shifted towards a more natural makeup style. In a 2023 episode of Vogue’s “Beauty Secrets,” she shared her transformed routine, saying her foundation now feels more natural and blends seamlessly into her skin. Reflecting on her past makeup habits, she noted a significant reduction in the amount she uses while still achieving her desired look. However, her passion for beauty products remains. “I enjoy scouting new makeup online,” she confessed.
Heavy Eye Makeup Through the Years
Kylie Jenner was once known for her dramatic eye makeup, characterized by heavy eyeliner and thick mascara. At Avril Lavigne’s Spring 2013 show, she sported bold lashes and dark lines around her eyes, complemented with subtle blush and glossy lipstick. However, her makeup style has evolved towards a more understated look. In her 2023 Vogue episode, she mentioned her preference for a delicate winged eyeliner to accentuate her eyes, crediting her natural lashes, which she inherited from her mother.
While mascara remains a staple in her routine, she now applies it more gently, focusing on the outer corners to create an almond shape. This led to the launch of her product, the Kylash Volume Mascara, which she meticulously developed for optimal performance.
Lip Liner Blunders
A staple in Jenner’s beauty routine is lip liner, which she uses to create the illusion of fuller lips. However, at a 2022 launch event for her makeup line, she encountered an issue with a mismatched lip liner that clashed with her lipstick—a mistake that resulted in a harsh line that detracted from her overall look. Alongside this, she also appeared to have overdone her contouring.
Her lips have long been a topic of discussion. In 2015, she confessed to receiving temporary lip fillers, addressing speculation about her cosmetic enhancements. Looking back, she expressed her insecurities regarding her natural lips and her initial efforts to enhance them with makeup before opting for fillers.
