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Kylie Jenner has literally grown up before our eyes. We were first introduced to her in 2007, when she debuted on “Keeping Up with the Kardashians” at 9-years-old , and she’s now pretty much unrecognizable from the little girl we saw running around the Kardashian-Jenner house in Calabasas, California. We’ve seen a few iterations of the Lip Kit queen since then, from the super glam, uber made-up King Kylie with blue hair, to the more demur and understated mom of two on the cover of British Vogue.
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This reality star has undergone a serious style evolution, and it’s all been intentional, according to her. “Constantly changing up my style makes me feel creative and it helps me with my confidence,” Jenner wrote in a 2015 post on her website (via People). “It makes me feel like a new person. I love feeling different and I love leaving the house knowing that nobody has ever seen me this way,” she added.
And it’s not just Jenner’s hair she likes to update to reflect how she feels. “I’m always changing my style or just expressing myself through fashion, so it’s all really fun and different,” she told WSJ Style in 2023. This style chameleon (who even has her on clothing line, Khy by Kylie Jenner) has had some truly iconic looks.
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Kylie Jenner wasted no time expressing herself through fashion
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Kylie Jenner showed us very early on that she was going to be a style icon. At the Dash Fall Fashion Show in March 2007, her bold outfit choice demonstrated a natural passion for fashion. The rising star rocked a black top, silver sequin cropped shrug, patterned leggings, silver shoes, a hot pink headband, and a hot pink tutu. And we have the tutu to thank for her impact on the fashion world. Jenner told WSJ Style she remembers becoming interested in fashion because of her mom, Kris Jenner, who sold tutus in her kids’ clothing boutique. “I had them in every color and pattern, and I just loved dressing up,” Jenner said.
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We saw the 10-year-old’s young, girly side come out again at KIIS-FM’s Wango Tango in May 2008. Jenner wore a pink tank top, flouncy black-and-white skirt with a tulle underlay, cropped black waistcoat, and black UGG boots. Not only was a young Jenner experimenting and expressing herself with her clothing, she was paying attention to trends, as waistcoats and UGGs were totally trendy.
Her style became more refined in 2009
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Kylie Jenner opted for young, cute clothing during her early forays on the red carpet, but we saw her adopt a slightly more refined style in 2009. She attended the Teen Choice Awards in a brown leather-look jacket over a flouncy white sundress with peep toe heels. This outfit illustrated Jenner’s penchant for girly looks with a little edge, and further proved she was all about the trends. The reality star layered several long necklaces around her neck (so cool for the time) and was starting to experiment with her hair, sporting choppy side-part bangs.
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The following month, she attended a Selena Gomez album release party in a strapless floral dress with a balloon skirt — which was also super on trend. The dress marked a style departure for Jenner, and gave us our first glimpse of the figure-hugging dress and heel combos we’d soon see a lot of. It was also one of her most grow-up choices to date, with the then 12-year-old growing up fast.
The Kardashian signature glam rubbed off on her in 2011
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We saw Kylie Jenner step out in some of her most Kardashian-esque pieces to date in 2011, suggesting her style was influenced by her uber glam sisters. That September, Jenner posed alongside big sis Kim Kardashian in a leopard print jumpsuit with black waist belt and black heeled pumps. The one-piece appeared to be the same one both Kim and Khloe Kardashian had worn, marking a stark move towards more grown up styles for the teen.
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In December, Kylie Jenner fit right in with her sisters again for the grand opening of Kardashian Khaos in Las Vegas. Jenner, who was only 14 at the time, wore the dress of the moment, a shiny silver bandage bodycon with sky-high platform nude heels.
Jenner admitted around that time that she relied a lot on her family’s wardrobes not only for inspo, but for pieces to borrow. “I raid my mom’s closet a lot, since we have the same size shoes. She has great bags,” she told Teen Vogue in 2013. Jenner also revealed that she would turn to her eldest sister Kourtney Kardashian for style advice, which explains why these outfits were better suited to someone in their 20s.
She began to carve out her own edgy style in 2013
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Kylie Jenner began leaning into her own style in 2013. In October, we saw a glimmer of her grungy side at the premiere of “Ender’s Game,” when she wore a dark graphic tee tucked into a terracotta skirt, accessorized with lace-up black boots and a black clutch. Jenner started experimenting more with her hair too, adding a lighter shade to the ends.
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The following month, she appeared on the American Music Awards red carpet in another outfit that demonstrated her evolving style. She ditched the super girly dresses and skirts. Instead, she rocked modern black bottoms and a cute and youthful white crop-top, which felt more authentic than her looks from raiding her family’s closets. She wore sheer black boots and was sporting flattering bangs for an extra modern, shaggy edge that was uber cool.
That year, Kendall Jenner spoke to Teen Vogue about her sister’s evolving style. “Kylie wears more black and I wear more color,” the future supermodel explained. “She likes edgier things that I wouldn’t necessarily wear.” These red carpet appearances confirmed that.
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She turned to more grunge looks in 2014 (when the blue hair first came to play)!
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Kylie Jenner’s aesthetic leaned toward sweet and girly until 2014, which is when we saw her edgy-yet-glam side poke through even more. This year is also when that notorious blue hair came out to play. For the Billboard Music Awards in May, Jenner wowed with dip-dye blue-black hair, pairing the new look with a figure-hugging spaghetti strap dress. She added criss-cross strap pointed toe heels to the all-white ensemble, letting her vibrant new ‘do shine. The look proved she was growing up fast (she was mere months away from her 17th birthday) and already knew how to dress.
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The white number showed Jenner’s glam side, but she also leaned more into the grunge aesthetic. At a book signing the following month, she looked more rocker than refined in a baggy T-shirt with a skull, which she paired with skin-tight shiny black pants. Jenner was clearly still working on her signature style — totally understandable for someone so young — but she later admitted to WSJ Style that this is the fashion era (which she dubbed “King Kylie”) she stands by the most.
2015 was all about the dialed up glam and lip filler
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Still experimenting, Kylie Jenner ditched the blue hair by 2015. She started wearing more the glamorous, sexy styles she’s become synonymous with, attending the GQ and Giorgio Armani Grammys After Party that February in a sheer, embellished silver dress with cutouts at the waist. This was also the year Jenner developed her signature beauty style, getting her first round of lip fillers.
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The beauty opened up about her lips on an episode of “Keeping Up with the Kardashians” in 2015, sharing (via ABC News), “I have temporary lip fillers, it’s just an insecurity of mine and it’s what I wanted to do.” Lip fillers quickly became just one of the many trends Jenner made popular.
The following month, Jenner amped up her sexy style and bold lips a little more. She appeared at a London event in chic all-black ensemble, complete with sheer top, peekaboo bra, and statement-making cape. The cape was a fun addition to Jenner’s otherwise dark aesthetic, while her see-through top and siren red lips gave a nod to the reality star’s sultry side. Jenner was becoming a successful young woman, and her sophisticated blunt bob and monochromatic look further reflected that.
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2017 focused on big hair changes and delicate outfits
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Don’t think Kylie Jenner’s 2016 bob meant she was over having fun with her hair. In 2017, Jenner, who’s been open about her love of wigs, made a lot of changes to her locks, also focusing more on delicate, beaded outfits instead of the bolder dresses we’d seen before. In April, she made a statement with yellow-green hair with black roots. She paired the look with a figure-hugging sparkly champagne dress, but made it edgier by adding unexpected chunky black boots. The neutral garment could have easily washed the star out, but her choice of wig added a pop of color that kept things balanced.
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The following month, Jenner attended her second Met Gala in one of her most glamorous looks ever. Jenner showed off yet another new ‘do, wearing a platinum blond bob with an ornate, sheer, beaded Versace dress. The light pink shade was gorgeous with her super light tresses and tan skin, and Jenner proved she’d clearly learned a lot about fashion and how she wanted to express herself.
In a clip from “Keeping Up with the Kardashians” spin-off “Life of Kylie,” Jenner made it very clear she knew what suited her and wanted the gown to be super form-fitting. “This is really loose,” she said, gesturing to her waist during a fitting. “It needs to be like this, where my body looks crazy. I need to kind of suffocate,” she added, cinching the dress in.
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Out-there fashion and big silhouettes were more her style in 2019
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Just when we thought Kylie Jenner didn’t have much more fashion experimentation in her, she brought out some of her boldest fashion moments ever. The star left the spotlight for a time while she was pregnant with her first child, but returned to the red carpet in 2019 in a big way. She walked the Grammy Awards’ red carpet in February in a very fashion-forward light pink custom pantsuit by Balmain, with huge sleeves and attached gloves. The over-the-top silhouette was incredibly daring, but Jenner stayed true to her signature style by belting it at the waist to show off her figure.
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Still, Jenner’s Grammy appearance was tame compared to her Met Gala dress that year. The custom Versace number continued Jenner’s pattern of wearing form-fitting dresses, showcasing her gorgeous hourglass curves. The all-purple mermaid-style dress looked great against her tan skin with giant balls of feathers on her arms and around the hem, plus a sparkly netting over the plunging nude slip. She kept her passion for unconventional hair going too, wearing a super sleek long purple wig.
“One of the most iconic memories and looks is my purple Versace,” she told WSJ Style. “I see a lot of my fans always love to repost that look and I think it’s just an iconic dress. I don’t normally wear purple so I think it’s like the one big purple moment I had,” she added. Jenner chose the perfect event to do something daring and she had just the right amount of confidence to pull it off.
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In 2022, Kylie Jenner kept it daring with sophisticated and seductive looks
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Kylie Jenner became a mom for the second time in 2022 and her style started to reflect life as grown woman. She attended the #BoF500 gala during Paris Fashion Week in one of her most grown-up and sophisticated one-pieces ever, a seductive all-lace black jumpsuit. The beauty had jaws dropping in the figure-hugging sheer ensemble, which felt like a sexier and more grown-up version of her 2019 Grammy outfit.
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It also had built-in gloves, but the black lace and multiple cut outs made it feel more mature. The look proved Jenner wasn’t afraid to set a trend, too. Sheer clothing became huge the following summer, and we can’t help but feel like Jenner may have had something to do with that. The star stuck with her signature deep brunette locks in a classy updo, which allowed her risqué jumpsuit to have its moment.
The following month, Jenner opted for black again at the CFDA Fashion Awards in a one-shoulder dress with a high-slit skirt. The Mugler gown was elegant and classic with a modern twist. It showed she hadn’t strayed too far from her signature body-hugging looks — and the thigh-high slit kept things super sexy. But the sheer sleeve, dark tone, and velvet skirt confirmed her style had changed. She explained to The New York Times in 2024 that a lot of her fashion transformation around this time was inspired by giving birth. “It takes me a while after I have a baby to feel like myself again. Then you get your body back, and you’re like, ‘Wait, the trends have changed,'” she shared.
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Kylie Jenner made serious fashion statements in 2023
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Kylie Jenner continued to show the world she hadn’t lost her fashion edge in 2023 as she seemingly became more confident with her post-baby body. In January, she took a big fashion risk at the Schiaparelli Haute Couture Spring Summer 2023 fashion show, wearing a black dress with a giant 3D faux lion head.
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The dress was oh-so Leo of her (embodying her luxury-loving lion zodiac so well), and it certainly got people talking. Though Jenner caught some heat for the divisive piece, the founder of the animal activist group PETA, Ingrid Newkirk, supported her decision. “Kylie’s look celebrates lions’ beauty and may be a statement against trophy hunting, in which lion families are torn apart to satisfy human egotism,” they told Sky News.
In March, Jenner showed us another side of her evolving style at the Vanity Fair Oscar party in something more dialed down. She wowed in one of her most classy and elegant dresses ever, a custom Maison Margiela piece featuring a large bow on the chest and a train. The dress made it clear that Jenner was choosing darker colors and less over-the-top silhouettes, suggesting her taste had matured as she got older.
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Vogue (and demure looks) called Kylie Jenner’s name in 2024
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In January 2024, Kylie Jenner got people talking for her strikingly different style at Paris Fashion Week. Her makeup was natural and she wore a light and airy beige strapless dress with a sweetheart neckline. Though the bodice was fitted, the tulle overlay wasn’t, marking a big departure in silhouette choice. And fans noticed. “I am absolutely loving this all natural Kylie look!!!!! you are glowing and stunning,” one fan commented after Jenner shared snaps to Instagram. But there was still a nod to her signature style, as she wore sky-high Perspex heels with a hefty platform.
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Jenner later wore a strapless cream satin gown to the Met Gala in May. It paid homage to ’50s style and was much more understated than her past outfits for the fashion event, cementing her more demure, stripped back style. Even her manicures became more understated around this time, as we spotted her rocking chic, garden-inspired nails.
Jenner touched on her new style in an interview with The New York Times in March, sharing, “I don’t have this thick mane down to my butt, I don’t have lash extensions, I don’t have these long claws.” She added, “(I’m) stripping down a little bit.” Clearly whatever she did was working. By this point, her style had become such a touchstone for the fashion community that she landed the September 2024 cover of British Vogue. And it was only fitting for this superstar who knows the importance of letting her fashion choices evolve as she does.
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