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Ever since her teen years on Keeping Up With The Kardashiansthe world has watched Kylie Jenner‘s style change and evolve with the times. No matter which fashion era she’s in at the moment, however, Jenner always serves looks.
Whether she’s wearing skin-tight bodycon dresses, two-piece matching sets or sparkling ball gowns, Jenner is known for her trendy and slightly edgy style. The youngest Kardashian-Jenner has always been willing to step out of the box when it comes to her outfits, and there’s no denying the influence she has over the fashion world.
Here’s a look at some of Kylie Jenner‘s best outfits of all time, from her days experimenting with bright hair and a punk-rock-chic look to the bold and glamorous dresses she wears today.
Kylie Jenner at the MTV Video Music Awards in 2014
Jenner looked put-together and glamorous at the 2014 VMAs in a silky black gown with a thigh-high slit. The reality star accessorized with some stacked bracelets and a long necklace. She kept her beauty look simple to keep the focus on the gown, wearing understated makeup and a carefree blowout.
Kylie Jenner at the American Music Awards in 2014
Jenner attended the 2014 AMAs with her sisters Kendall Jenner and Khloé Kardashian by her side. She managed to pull off an elegant yet spunky look in a red silk Alexandre Vauthier gown with a thigh-high slit and plunging neckline.
Kylie Jenner at an event in New York City in 2014
While attending a DuJour Magazine event that celebrated her Bruce Weber photoshoot at Lavo Restaurant in New York City, Jenner opted for a ’90s grunge-inspired look. She wore a black crop top with low-rise black trousers, black heels and a black leather jacket draped over her shoulders.
Kylie Jenner at a Grammys afterparty in 2015
Jenner arrived at the GQ and Giorgio Armani Grammys afterparty in full glam. She wore a long-sleeve sheer sparkling gown that featured side cutouts and a short train.
Kylie Jenner at the ESPYS in 2015
The beauty mogul walked the red carpet at the 2015 ESPYS with her sister Kendall, and her dress out-sparkled almost everyone else there. The teen wore a gown by Lebanese designer Shady Zeineldine, which featured allover gold sequins and a turtleneck style.
Kylie Jenner running errands in Los Angeles in 2015
Jenner was spotted out and about in Los Angeles in July 2015 wearing a matching two-piece brown suede set. Her light blue hair color is what really made the look stand out, and she paired the set with gold heels and simple gold jewelry.
Kylie Jenner at the opening of Sugar Factory in New York City in 2015
When Jenner attended the grand opening of the Sugar Factory in New York City in 2015, she kept her look simple but glamorous in a white crop top and matching high-slit skirt by Zachary the Label. That night, Jenner also debuted long green hair for the first time.
Kylie Jenner at Coachella in 2015
The Kylie Cosmetics founder kept the long green hair going when she attended Coachella in 2015, where she hung out with her sister Kendall and friend Hailey Bieber. Jenner wore a cream-colored crop top and matching high-waisted shorts with an ankle-length white vest, chunky sneakers and a gray hat.
Kylie Jenner at the Kanye West Yeezy Season 3 fashion show in 2016
Kanye West and Balmain creative director Olivier Rousteing designed the clothes Jenner and the rest of her family wore to the launch of Yeezy Season 3. The youngest Kardashian-Jenner wore a sparkling tank with tons of detail along with a ripped cream-colored miniskirt. For accessories, she wore slouchy white calf-length boots and held a white fur shawl. The black beanie completed the took and really tapped into Jenner’s personal style.
Kylie Jenner at the Met Gala in 2016
In 2016, Jenner made her Met Gala debut in a sparkling gown. The theme was “Manus x Machina: Fashion In An Age of Technology,” and Jenner opted for a structured Balmain gown complete with beading and fringe. The teen kept her beauty look simple with nude lips and a black bob.
Kylie Jenner at a Prabal Gurung fashion show in 2016
In 2016, Jenner attended the Prabal Gurung presentation in a blue-and-white patterned suit and a sheer black crop top. The matching set had a little bit of an edge to it, and Jenner played that up with a sultry smokey eye and a nude lip. She kept her blonde hair in loose waves and wore sandals.
Kylie Jenner at the Met Gala in 2017
For her second Met Gala, Jenner wore a custom sheer nude Versace gown, embellished with more than 7,000 crystals and sparkling fringe. Her hair was styled in a short platinum blonde bob, and she actually appeared on the red carpet with Donatella Versace.
Kylie Jenner at the Met Gala in 2018
While Jenner’s first two Met Gala outfits were full of sparkle, her third, for the “Heavenly Bodies: Fashion and the Catholic Imagination” theme, was a little more subdued. For her red carpet debut just three months after giving birth to her daughter StormiJenner wore a black Alexander Wang gown with a cutout on her stomach.
She accessorized with small mirrored sunglasses and Chopard diamond earrings that featured two 5-carat diamonds. Jenner later said she had to add a zipper to the gown before the event after a wardrobe malfunction.
Kylie Jenner celebrating her 21st birthday in 2018
It was no surprise that Jenner went full-on glam for her 21st birthday celebration in August 2018. The reality star wore a bright pink Peter Dundas dress with matching Olgana Paris heels for a family dinner at Craig’s in Los Angeles. Later in the night, Jenner changed into a sparkling LaBourjoisie jumpsuit made with over 70,000 Swarovski crystals and pink suede Christian Louboutin heels.
Kylie Jenner at the MTV Video Music Awards in 2018
Jenner showed up at the 2018 VMAs to support her boyfriend, Travis Scottwearing an ivory double-breasted mini dress by Tom Ford with a pair of white heels. She slicked her blonde hair back into a bun with a deep side part.
Kylie Jenner walking in New York City in 2018
While in Manhattan alongside Scott for his Astroworld tour, Jenner stepped out one night wearing a denim jumpsuit with a belted detail and a zipper down the front. She paired the jumpsuit with snakeskin ankle boots and left her long gray hair down.
Kylie Jenner walking in Los Angeles in 2018
While out in L.A., Jenner ditched the party dress for something a bit more understated. She was photographed wearing high-waisted Alexander Wang pants with a white crop top and clear heels. She kept her makeup minimal and wore her long dark hair in a low ponytail.
Kylie Jenner at the Met Gala in 2019
Jenner went all out for the 2019 Met Gala in a head-to-toe lilac Versace gown with a mermaid silhouette, fur arms and skirt, and a plunging neckline. She even added a matching bright purple wig. She matched with her sister, Kendall, who wore a similar orange gown. The two walked the red carpet together.
Kylie Jenner at a pre-Grammys event in 2019
After hosting her daughter Stormi’s 1st birthday party, Jenner headed to Clive Davis and The Recording Academy’s Annual Pre-Grammy Gala alongside Scott. The star channeled Old Hollywood glamour in a silky red gown with a thigh-high slit and oversized bow detail.
Kylie Jenner at the premiere of Travis Scott: Look Mom I Can Fly in 2019
Jenner showed support for her then-boyfriend Scott when she attended the L.A. premiere of his Netflix documentary, Look Mom I Can Fly. The reality star wore a strappy white dress with a long choker detail and matching white heels. She put her hair in a high, bouncy ponytail and added some jewels. Even cuter? Jenner and Scott brought along their daughter Stormi for some adorable family photos snapped on the red carpet.
Kylie Jenner walking in New York City in 2019
While spending some time in New York City, Jenner stepped out in a unique ensemble. She wore an oversized pinstripe blazer as a mini dress and paired it with glittering fishnet pants. She styled her hair in a slick bun and added some hoop earrings.
Kylie Jenner at the Vanity Fair Oscars afterparty in 2020
Jenner stunned at the 2020 Vanity Fair Oscars afterparty in a form-fitting blue strapless gown by Ralph & Russo. With plenty of sparkles and an hourglass silhouette, the gown was a showstopper.
Kylie Jenner at a Tom Ford show in 2020
Jenner made an appearance at a Tom Ford fashion show in Hollywood. The star wore a dazzling silver mini dress made of black netting and tons of sequins. She paired the dress with thin-strapped heels and a Tom Ford clutch, adding some large rings for extra glitz.
Kylie Jenner at the 72nd Annual Parsons Benefit in 2021
Although Jenner and Scott were broken up at the time, the two looked like family at the 72nd Annual Parsons Benefit in New York City. The duo walked the red carpet with their daughter, Stormi, and Jenner opted for a unique dress and Old Hollywood waves for some added glamour. Her figure-fitting gown came in various shades of green, and she added long matching sheer gloves and a pair of clear heels.
Kylie Jenner in New York City in 2021
Jenner showed off her baby bump while spending some time in Manhattan in September 2021. The star wore a tight black lace bodysuit with a long black velvet coat and a pair of black heels.
Kylie Jenner in New York City in 2021
In all-black one night and all-white another night, Jenner served up several looks while in Manhattan in September 2021. On this night, she wore a white mini dress that clearly put her baby bump in view, along with an ankle-length white leather coat and clear heels. She added a tiny white bag and was all smiles as she strolled down the street.
Kylie Jenner in New York City in 2021
Jenner put her bare baby bump on full display in a knotted crop top and wide-legged black jeans while in New York City. She added some color with a long, bright orange coat and matching pointy-toe heels.
Kylie Jenner at the Billboard Music Awards in 2022
Jenner made an appearance at the 2022 Billboard Music Awards alongside Scott and daughter Stormi. She wore a silver fitted column gown with gold arm cuffs and nude sandals.
Kylie Jenner at the CFDA Fashion Awards in 2022
The mom-of-two wore a one-shoulder, high-slit black Mugler gown to the CFDA Fashion Awards in 2022. She coordinated with her mother, Kris Jennerwho donned a black Schiaparelli dress.
Kylie Jenner at the opening of the Thierry Mugler: Couturissime exhibit at the Brooklyn Museum in 2022
The Kardashians star attended the opening of Brooklyn Museum’s Mugler exhibit wearing a design by the late fashion genius himself. Her look, which consisted of a black, corset-style gown with feather details, matching gloves and an elaborate headpiece was straight out of the Mugler archives.
Kylie Jenner at the Schiaparelli Haute Couture Show in 2023
The beauty mogul stepped out during Paris Fashion Week wearing a dramatic lion’s head gown. The look, which was designed by Schiaparelli, featured a faux life-sized lion’s head affixed onto a form-fitting black velvet dress.
“BEAUTY AND THE BEAST. thank you @danielroseberry and @schiaparelli for such a special morning,” Jenner wrote on Instagram. “wow i loved wearing this faux art creation constructed by hand using manmade materials. beautiful beautiful.”
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