Image: Kylie Jenner at Wall Street Journal event 2023.
Kylie Jenner. AFP via Getty Images

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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Image: Kylie Jenner with Caitlyn (then known as Bruce) Jenner and Kendall Jenner in the premiere of Teacher
Kylie Jenner with her father, Caitlyn Jenner, and her sister, Kendall Jenner. WireImage for Hollywood Reporter

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.

Image: Kylie Jenner at the season 1 viewing party for KUWTK in 2007 with Kim Kardashian and Kendall Jenner.
Kylie Jenner with Kim Kardashian and Kendall Jenner. WireImage

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.

Image: Kylie Jenner at Food & Wine Presents the Taste of Beverly Hills2010.
Kylie Jenner. FilmMagic

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.

Image: Kylie Jenner at 2012 Erase MS Benefit.
Kylie Jenner. WireImage

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.

Image: Kylie Jenner at MTV Movie Awards 2013
Kylie Jenner. WireImage

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.

Image: Kylie Jenner at After Earth premiere 2013.
Kylie Jenner. WireImage

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.

Image: Kylie Jenner at Justin Bieber
Kylie Jenner. FilmMagic

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.

Image: Kylie Jenner at 2014 MTV VMAs.
Kylie Jenner. WireImage

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.

Image: Kylie Jenner in NYC 2014.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner at 2014 AMAs.
Kylie Jenner. FilmMagic

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.

Image: Kylie Jenner in Los Angeles 2015.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner in Los Angeles 2015.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner at Vera Wang NYFW Spring 2015 show.
Kylie Jenner. Getty Images

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.

Image: Kylie Jenner at Balmain x H&M launch in 2015
Kylie Jenner. Getty Images for H&M

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.

Image: Kylie Jenner at 2015 AMAs.
Kylie Jenner. FilmMagic

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.

Image: Kylie Jenner at the Met Gala 2016.
Kylie Jenner. Getty Images

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.

Image: Kylie Jenner at a Harper
Kylie Jenner. Getty Images

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.

Image: Kylie Jenner in NYC 2016.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner in NYC 2017.
Kylie Jenner. GC Images
Image: Kylie Jenner in NYC 2017.
Kylie Jenner. Nicholas Hunt

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.

Image: Kylie Jenner in NYC 2017.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner at the 2017 Met Gala.
Kylie Jenner. WireImage

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.

Image: Kylie Jenner at the 2018 Met Gala.
Kylie Jenner. Karwai Tang/Getty Images

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.

Image: Kylie Jenner in Los Angeles 2018.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner in NYC 2018.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner at the 2019 Grammys.
Kylie Jenner. FilmMagic

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.

Image: Kylie Jenner. in NYC 2019.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner at the Met Gala 2019.
Kylie Jenner. FilmMagic

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.

Image: Kylie Jenner at the 2020 Vanity Fair Oscar Party.
Kylie Jenner. Getty Images

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.

Image: Kylie Jenner in Los Angeles 2021.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner in NYC 2021.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner at the 2021 Parsons benefit with Travis Scott and Stormi Webster.
Kylie Jenner with Travis Scott and their daughter, Stormi Webster. Getty Images for The New School

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.

Image: Kylie Jenner at PFW 2022.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner at a Business of Fashion Event in 2022.
Kylie Jenner. WireImage

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.

Image: Kylie Jenner at a Mugler event in 2022.
Kylie Jenner. WireImage

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.

Image: Kylie Jenner in LA 2022.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner at PFW 2023.
Kylie Jenner. Getty Images

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.

Image: Kylie Jenner in LA 2023.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner at PFW 2023.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner in LA 2023.
Kylie Jenner. GC Images

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.

Image: Kylie Jenner at Wall Street Journal event 2023.
Kylie Jenner. Getty Images for WSJ. Magazine I

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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Kay Adams