From a young age, Kylie Jenner has lived her life in the public eye. Growing up in front of cameras, she gained widespread recognition through Keeping Up With The Kardashians, which debuted when she was just 10 years old.
While her family’s fame opened the doors for her opportunities, Jenner has established herself in the entertainment and business world. Her first foray into the fashion industry came in 2013, when she and her sister, Kendall, launched a line in collaboration with PacSun. She then branched into beauty with the launch of Kylie Cosmetics in 2015, starting with her lip kits and eventually expanding into skincare. In a few short years, her business acumen and global influence earned her the title of the world’s youngest self-made billionaire at only 21. Forbes subsequently alleged document manipulation, but Jenner retained a spot on their list of richest self-made women in 2020, with a $700 million net worth.
It wasn’t until recently that Jenner expanded her fashion portfolio and debuted her very own line, Khy. Within the first hour of the launch, the brand earned $1 million.
Jenner’s bold approach to her business ventures mirrors her fearless sartorial choices. She unapologetically experiments with daring choices and consistently showcases her dynamic style, refusing to be confined to a single category. While she has long favored colorful, vibrant styles in both her fashion and beauty aesthetic, this year has seen a notable shift as she embraces a more minimalist, quiet luxury approach.
Ahead, see how Jenner’s sartorial sense has developed from following youthful trends to a more sophisticated, eclectic and unique style that reflects her evolving tastes and influences.
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2004, World Premiere of Teacher’s Pet
With her family in the limelight, some of Jenner’s first red carpet appearances took place from an early age. She attended the world premiere of Teacher’s Pet with her sister, Kendall, and her father, Caitlyn, where the six-year-old wore a printed skirt and a pink zip-up jacket with knee-high boots.
2007, Keeping Up With The Kardashians Viewing Party
For the Keeping Up With The Kardashians season one viewing party, Jenner wore a pink tulle dress with silver embellishments and a pair of silver ballet flats.
2010, Food & Wine Presents the Taste of Beverly Hills
It’s no surprise that with many cameras on her at such a young age, Jenner quickly developed a keen sense of fashion. On the opening night of The Taste of Beverly Hills, she wore a grey belted mini dress and black platform heels.
2012, Annual Race to Erase MS Event
At a benefit, Jenner wore a black maxi dress with a sheer skirt, Christian Louboutin spike peep-toe pumps and drop earrings.
2013, MTV Movie Awards
Jenner arrived at the MTV Movie Awards in a white crop top and beige pencil skirt, paired with Gianvito Rossi nude pointed-toe pumps. She accessorized with a gold chain necklace and Cartier bracelets and rings. She also juxtaposed her otherwise light and summery outfit with smoky eyeshadow.
2013, After Earth New York Premiere
Jenner’s style changed dramatically around 2013, when she started going for a more mature aesthetic. She showcased her new look at the After Earth premiere, in a black crop top and a black Mugler asymmetrical skirt, with open-toe caged boots from Balmain.
2013, Justin Bieber’s Believe Premiere
Jenner paired a white crop top and a long, slitted black skirt with Aquazzura lace-up heels at the Justin Bieber’s Believe premiere. She accessorized with a hefty stack of Cartier love bracelets and rings, a jewelry signature for her at the time.
2014, MTV Video Music Awards
Jenner revealed a more elegant, sophisticated look at the VMAs, in an Alexandre Vauthier satin wrap dress with a daring slit and black Gucci T-strap pumps, with her shorter hair in a more mature, blown-out style.
2014, in New York City
While shopping in NYC, Jenner showed off her knack for street style in a model-off-duty aesthetic: an oversized Marques Almeida denim shirt dress, black thigh-high boots and edgy mesh gloves. She accessorized with a gold Rolex watch and Cartier Juste un Clou bracelet.
2014, American Music Awards
Even as a teenager, Jenner was not one to shy away from risky styles—including unexpected hair colors. In 2014, Jenner was all about blue ombré, and her hair took center stage when she arrived at the AMAs in a daring burgundy satin Alexandre Vauthier gown, paired with black mesh pumps and, of course, a Cartier stack.
2015, in Los Angeles
While running errands in L.A., Jenner showed off her newly-colored light blue hair while dressed in a brown suede crop top and matching trousers. She accessorized with gold Tamara Mellon heels, Dior sunglasses and her usual Cartier bracelet stack.
2015, in Los Angeles
Jenner proved she isn’t a sweatpants-and-hoodie type of traveler when she arrived at LAX in a light grey long-sleeve dress from Minkpink and the Adidas superstar sneakers that were oh-so-trendy at the time. She accessorized with a tan Hermès Birkin bag.
2015, in New York City
Jenner sat front row at Vera Wang’s Spring 2016 show at NYFW. She donned one of the all-black outfits from the collection: a crop top and suit with shoulder cut-outs, paired with trousers. She finished off the ensemble with black stilettos from Gianvito Rossi and a brown lip.
2015, Balmain x H&M Collection Launch Party
To celebrate the Balmain x H&M launch, Jenner opted for some statement pieces from the collection. While many celebrities attended in simpler outfits, Jenner chose the gold-embroidered black mini dress along with suede thigh-high boots.
2015, American Music Awards
Only a week before the launch of Kylie Cosmetics—which was first named Kylie Lip Kits—Jenner attended the 2015 AMAs in yet another bold look. She wore a leather dress with chain embellishments from Bryan Hearns and black Tamara Mellon heels. She also matched the silver details from her dress with a white gold Cartier love bracelet.
2016, Met Gala
For her Met Gala debut, Jenner embodied the “Fashion in an Age of Technology” theme in a Balmain crystal-embellished gown designed by Olivier Rousteing. She kept her makeup simple with a bronzy eye and a nude lip.
2016, Harper’s Bazaar “Icons by Carine Roitfeld”
To kick off New York Fashion Week, Jenner arrived at the always star-studded Harper’s Bazaar event in a pink Balmain tassel mini dress with pearl embellishments and Yeezy heels.
2016, in New York City
For Alexander Wang’s Spring/Summer 2017 show, Jenner embraced the fringe comeback in an Alexander Wang mini dress and black kitten heels, along with a fresh blonde ‘do.
2017, in New York City
At the next NYFW, Jenner braved the winter cold in a tan fur coat and rose gold pumps. Later that evening, she attended the Jeremy Scott Spring 2017 show in a two-piece ensemble with rose gold chains.
2017, in New York City
On her way to Travis Scott’s birthday party, Jenner went for a casual, sporty look. She wore a black track jacket from Reebok’s collaboration with Vetements and paired it with black cropped leggings. She added a feminine touch to her outfit with Dsquared2 lace-up heels.
2017, Met Gala
For Jenner’s second Met Gala appearance, she donned a mesh gown adorned with sparkling embellishments and dramatic fringe. She also wore a platinum bob wig, paying homage to Rei Kawakubo’s signature hairstyle, which was rather fitting given that year’s “Comme des Garçons: Art of the In-Between” theme.
2018, Met Gala
Just three months after welcoming her first child, Jenner returned to the red carpet at the Met Gala. She wore a fitted black Alexander Wang gown and accessorized with bejeweled sunglasses from the brand’s collaboration with Gentle Monster, along with diamond stud earrings.
2018, in Los Angeles
Jenner channeled Barbie on her 21st birthday. Not only did she wear pink, but she committed to the theme by dyeing her hair golden blonde, which took two days to accomplish. Her first outfit of the night was a pink satin minidress by Peter Dundas and Olgana Paris heels. Later that evening, she changed into a custom crystal-embellished romper by Labourjoisie, which, according to Glamour, featured 70,000 Swarovski crystals that cost about $8,000. She styled her hair in a sleek, high ponytail, and completed the look with pink Christian Louboutin heels and a crystal orb clutch from Marzook.
2018, in New York City
On her way to join her then-partner, Travis Scott, on his Astroworld tour, Jenner showed off her platinum blonde hair while outfitted in a denim jumpsuit from Iro, paired with snakeskin boots and a Dior saddle bag.
2019, 61st Annual Grammys
Jenner made an appearance at the 2019 Grammys to support Travis Scott, who was nominated for three categories. For the occasion, Jenner wore a pink Balmain ensemble featured in the brand’s Paris show the previous month.
2019, in New York City
Jenner certainly knows how to make business attire chic. On her way to dinner in New York, she wore a pinstripe blazer and sparkling mesh trousers from Mach & Mach’s Fall/Winter 2019 collection, adding a subtle, glamorous touch to the look. Jenner completed the ensemble with a pair of Alexander Wang mesh slingback heels and silver hoop earrings.
2019, Met Gala
Jenner’s take on “Camp: Notes on Fashion” was perhaps her most striking Met Gala look to date. She donned a mesh crystal-embellished feathered gown with matching sleeves, courtesy of Versace. To enhance the monochromatic allure of her outfit, she wore a matching wig, adding a playful spirit to the camp theme.
2020, Vanity Fair Oscar Party
In one of her last public appearances before the COVID-19 pandemic, Jenner turned heads in a dazzling dark blue couture gown from Ralph & Russo’s Spring 2020 collection, paired with Lorraine Schwartz diamond rings.
2021, in Los Angeles
To celebrate Justin Bieber’s sixth studio album release, Jenner wore a red cutout velvet bodysuit and matching asymmetrical mini skirt from LaQuan Smith, paired with Givenchy stilettos. She layered up with a red leather coat from Art School London’s Autumn/Winter 2021 collection and accessorized with a Louis Vuitton monogram bag.
2021, in New York City
Just two days after announcing her second pregnancy, Jenner showed off her baby bump on her way to the LaQuan Smith NYFW show. She donned a see-through lace jumpsuit from the brand’s Spring 2021 collection, plus black mules from Studio Bakovic and a black coat.
2021, Parsons Event 72nd Annual Parsons Benefit
Jenner attended the 72nd Annual Parsons Benefit with Travis Scott and their daughter, Stormi. For the occasion, Jenner wore a vintage couture dress from Jean Paul Gaultier’s Spring 1987 collection and styled her hair in 1920s-inspired finger waves. Later that evening, Scott was among the creatives honored for his design contributions to the sneaker and streetwear world.
2022, in Paris
Jenner went for a casual street style vibe at the Loewe Spring/Summer 2023 show at Paris Fashion Week. She attended in an all-Loewe ensemble: a white tank top and white men’s briefs paired with a long grey coat and black sunglasses. Jenner also wore the black inflated heels later seen in the show.
2022, Business of Fashion Event
Jenner attended the Business of Fashion gala celebrating the 2022 BoF 500 in an asymmetrical cutout lace dress designed by Casey Cadwallader, paired with black pumps and accessorized with silver studs. To complement the romantic look, she wore her hair in a loose, wavy updo.
2022, Thierry Mugler Event
To celebrate the Thierry Mugler Couturissime exhibition opening at the Brooklyn Museum, Jenner exuded futuristic glamour in an archived black silk and satin gown adorned with ostrich feathers from the fashion house’s Fall 1995 collection. She completed the look with a tiara from the Fall/Winter 1999 collection.
2022, in Los Angeles
Jenner stepped into Giorgio Baldi, a celebrity-favorite Italian restaurant in Santa Monica, in an all-black leather ensemble. She embodied an effortlessly cool vibe with a David Koma biker jacket with matching pants and pointy-toed boots. Jenner also added a pop of color with blue sunglasses.
2023, in Paris
For Schiaparelli’s Haute Couture Spring/Summer 2023 show, Jenner wore one of the looks presented on the runway: a faux fur lion head attached to a velvet dress. She completed her ensemble with Schiaparelli’s gold toe pumps and eye stud earrings.
2023, in Los Angeles
To celebrate a friend’s 40th birthday party in L.A., Jenner wore an all-black outfit: a draped top and sheer satin mini skirt from Acne Studios, Calzedonia tights, a leather trench coat and kitten high heels.
2023, in Paris
During Paris Fashion Week, Jenner dazzled in a custom Schiaparelli haute couture silver dress designed by creative director Daniel Roseberry, as she supported her sister, Kendall, who closed the show.
2023, in Santa Monica
At the Khy launch party, Jenner showcased her fashion flair in an all-faux-leather ensemble from her new clothing brand. Her friends and family appeared at the event in different pieces from the collection, while Jenner donned a black open-back top, black pants, and a pair of sunglasses from her new line.
2023, Wall Street Journal Magazine Innovator Awards
In 2023, Jenner was honored with the Brand Innovator of the Year award for her newly launched clothing brand. For the occasion, she donned a Ferragamo dress featuring a latex bustier and a long skirt, showcased in the brand’s Spring 2024 collection. She accessorized with simple gold earrings and styled her hair in a wavy, blown-out look.
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