Each of the five Kardashian-Jenner sisters has had their own fashion journey. Kim loves a sensual style with a sporty touch, Kourtney has moved from trendy to grungy, Khloe favors stylish activewear, and Kendall’s model-off-duty look is clean and chic. Kylie Jenner’s outfits, however, are often more surprising than her older sisters’.
From bold colors to body-hugging styles and simple French-girl looks, you never know what Kylie will wear next. We love that she keeps us guessing! While her sisters have clear styles, Jenner enjoys trying out different looks, and with so many designers available to her, it makes sense to mix things up.
Kylie Jenner’s outfits—whether on the red carpet or in everyday life—offer lots of fashion ideas for everyone. To help you keep track of the beauty mogul and mom of two’s best looks, we’ve picked out some of our favorites.
KYLIE JENNER IN L.A. IN AUGUST 2018
The Kardashian-Jenners are all about that Barbie vibe, and Kylie is definitely no exception. It’s hard to pick what we love most about this look—the stunning dress, the chic shoes, or the sleek platinum ponytail!
KYLIE JENNER AT THE MTV VMAS IN 2018
There’s no need to tell you that the business owner and founder is a boss; this sharp blazer dress outfit speaks for itself.
KYLIE JENNER IN N.Y.C. IN NOVEMBER 2018
Why go for denim-on-denim with separates when you can nail the Canadian Tuxedo look with a stylish jumpsuit? This all-denim outfit is definitely one we can support.
KYLIE JENNER AT THE GRAMMY AWARDS IN 2019
Balmain suits Jenner perfectly, as shown by this blush pink jumpsuit with dramatic sleeves she wore to the Grammys. We imagine this one-piece is as comfy as it is beautiful; it’s a nice change from her usual body-hugging dresses, and we love it!
KYLIE JENNER AT THE MET GALA IN 2019
At one point, Jenner had a purple phase. She brought back her signature color for the 2019 Met Gala and perfectly captured the “Camp: Notes on Fashion” theme.
SOPHISTICATED SEXY
For the premiere of Travis Scott: Look Mom I Can Fly, Jenner chose an outfit that exuded sophistication. The white bodycon dress highlighted her signature curves, while the sexy back cutouts added a fun twist. We also loved the addition of the bow choker!
KYLIE JENNER AT THE ‘VANITY FAIR’ OSCAR PARTY IN 2021
This mermaid-style gown from Ralph and Russo combines sparkly fun with Old Hollywood glamour. Jenner said the look was worth it, even though it made sitting down a bit tricky!
KYLIE JENNER IN L.A. IN MARCH 2021
Is it just a coincidence that Jenner wore a strikingly similar outfit to celebrate the Haqq sisters’ birthday in 2023, just like she did in 2021 at the same venue? The only difference is the color: red instead of black. It just goes to show that even celebrities repeat outfits—sort of!
KYLIE JENNER AT THE BALMAIN SHOW AT PARIS FASHION WEEK IN SEPTEMBER 2022
Having designer friends definitely pays off, especially when they create exclusive looks just for you. Jenner has been a muse for many designers, but this crochet minidress by Balmain’s Olivier Rousteing is one of our top five favorites.
KYLIE JENNER IN PARIS IN SEPTEMBER 2022
Jenner is a strong supporter of the underwear-as-outerwear trend. She paired white hipster briefs with a matching tank top, black tights that blend into her boots, and a grey overcoat on top—simple yet absolutely showstopping!
KYLIE JENNER AT THE THE BOF 500 GALA IN PARIS IN 2022
Jenner is no stranger to a mesh look, but this outfit from the Business of Fashion 500 gala in Paris last fall really caught our eye. Custom-made for her by Casey Cadwallader, the creative director of Mugler, it features a stunning design of asymmetrical lace.
KYLIE JENNER AT THE COPERNI SHOW AT PARIS FASHION WEEK IN SEPTEMBER 2022
Although Jenner has recently been seen in more neutral tones, she’s always been “a big fan of color,” as Lizzie McGuire’s Miranda Sanchez would say. She particularly shines in blue, making the floral minidress she wore front row at the Coperni Spring/Summer 2023 show a must-have on this list. Don’t miss the matching sunglasses and heels!
KYLIE JENNER IN N.Y.C. IN NOVEMBER 2022
Jenner has certainly influenced many street style trends, but we think she may have borrowed the no-pants look from her big sister Kendall. Regardless, she nails the leggy style with a neutral base, an oversized black trench coat, and pointed-toe heels.
KYLIE JENNER IN ARCHIVE MUGLER AT THE MUGLER COUTURISSIME OPENING IN N.Y.C. IN 2022
At the Mugler Couturissime exhibition opening, Jenner called herself the “Mugler king” on Instagram. Given that it’s been almost a year since the event and we’re still talking about her look, we definitely agree! The Morticia Addams-inspired corset dress is fabulous on its own, but her headpiece would have turned heads even without it.
KYLIE JENNER IN PARIS IN FEBRUARY 2023
Remember when Jenner experimented with bright pastel hair colors? Well, blue is still her go-to! For an afternoon stroll in Paris, the mom of two wore a long-sleeved, body-hugging midi dress in a striking blue shade, pairing it with glittering Barbie-pink boots.
KYLIE JENNER IN L.A. IN MARCH 2023
It’s no surprise that for Malika and Khadijah Haqq’s 40th birthday, the youngest Jenner celebrated in style. The Kylie Cosmetics founder dazzled in a sexy set featuring a satin miniskirt and a matching black satin peek-a-boo mesh top. She completed the look with a leather trench coat, sheer black tights, and pointed-toe heels.
KYLIE JENNER IN MAISON MARGIELA AT THE ‘VANITY FAIR’ OSCAR PARTY IN 2023
Maison Margiela custom-made Jenner’s stunning metallic gown for the 2023 Vanity Fair Oscar Party, and the design did not disappoint. The original piece featured a statement bow tied at the bust and a cape train flowing from her mid-back. The only way this look could have been better is if the beauty mogul arrived in the Batmobile, because it’s definitely giving “superhero, but make it fashion.”
KYLIE JENNER IN JEAN PAUL GAULTIER AT THE MET GALA IN 2023
If anyone knows how to make a statement on the red carpet, it’s Kylie. The Haider Ackermann for Jean Paul Gaultier gown she wore to the 2023 Met Gala turned heads with every step. With its asymmetrical neckline, cold shoulder, and high thigh slit, this fiery ensemble was undoubtedly one of her best looks.
KYLIE JENNER IN PARIS IN MAY 2023
Jenner made a splash in the quiet luxury trend while in Paris. The reality star wore a crisp white midi dress with a corset waist and matching heels, keeping her accessories simple with small silver hoops, black sunglasses, and a tiny white handbag.
CONCLUSION
Kylie Jenner’s impact on the fashion world is undeniable. Her bold, daring, and often trendsetting outfits have captivated audiences worldwide, cementing her status as a style icon. From her early days as a reality TV star to her current role as a successful businesswoman and influencer, Jenner’s fashion choices have continued to evolve and inspire.
The outfits featured in this list represent just a glimpse of Jenner’s extensive style repertoire. Her ability to seamlessly blend high fashion with streetwear, her willingness to experiment with bold trends, and her knack for creating iconic looks have solidified her place in fashion history. As Jenner’s career continues to flourish, it is clear that her influence on the fashion industry will only grow stronger.
