Kylie Jenner's 19 Most Talked-About Outfits Ever

Kylie Jenner in Paris in May 2023

Kylie Jenner outfits — MEGA/GC Images/Getty Images

Jenner made a splash when she dabbled in the quiet luxury trend while in Paris. The reality star stepped out in a crisp white midi dress with a corset waist and matching heels and accessorized simply with a small pair of silver hoops, black sunglasses, and a miniature white handbag.

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Kylie Jenner in Jean Paul Gaultier at the Met Gala in 2023

Kylie Jenner outfts — Taylor Hill/Getty Images

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 each step she took. From its asymmetrical neckline, cold shoulder, and high thigh slit, the fiery ensemble was no doubt one of her best.

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Kylie Jenner in Maison Margiela at the ‘Vanity Fair’ Oscar Party in 2023

Maison Margiela custom-made Jenner’s ultra-metallic 2023 Vanity Fair Oscar Party gown and the designer’s vision did not disappoint. The original piece included a statement bow tied at the bust and a cape train falling from Jenner’s mid-back. The only way this look could have been better is if the beauty mogul pulled up to the event in the Batmobile, because it’s giving “superhero, but make it fashion.”

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Kylie Jenner in L.A. in March 2023

It should come as no surprise that for Malika and Khadijah Haqq’s 40th birthday, the youngest Jenner would celebrate in style. The Kylie Cosmetics founder came dressed to the nines in a sexy set that consisted of a satin miniskirt and matching black satin peek-a-boo mesh top. She finished off the look with a leather trench, sheer black tights, and pointed-toe heels.

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Kylie Jenner in Paris in February 2023

Remember when Jenner went through a phase of coloring her hair bright pastel hues? Well, blue is still her color. For an afternoon sauntering around Paris, the mama of two stepped out in a long-sleeved, body-hugging midi dress in a striking blue shade, and paired the one-and-done item with glittering Barbie-pink boots.

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Kylie Jenner in Archive Mugler at the Mugler Couturissime Opening in N.Y.C. in 2022

For the Mugler Couturissime exhibition opening, Jenner dubbed herself the “Mugler king” on Instagram. Given that it’s been almost a year since the grand event and we’re still discussing her look, clearly, we concur. As if this Morticia Addams-esque corset dress weren’t fabulous enough, we don’t doubt that Jenner’s headpiece would have turned heads on its own.

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Kylie Jenner in N.Y.C. in November 2022

Jenner has helped shepherd many street style trends, but we're pretty sure she borrowed the no-pants technique from big sister Kendall. Either way, the businesswoman nails the leggy look with a neutral base, an oversized black trench coat, and pointed-toe heels.

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Kylie Jenner at the Coperni Show at Paris Fashion Week in September 2022

Though Jenner’s been spotted in more neutral color palettes as of late, she’s always been, as Lizzie McGuire’s Miranda Sanchez once said, “a big fan of color.” Jenner especially shines in blue, so the floral minidress she wore front row at the Coperni Spring/Summer 2023 show deserved a spot on this list. Note the matching sunglasses and heels.

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Kylie Jenner at the the BoF 500 Gala in Paris in 2022

Jenner is no stranger to a mesh moment, but there’s something about this particular look from the Business of Fashion 500 gala she attended in Paris last fall that captured our attention almost instantly. It was custom-made for Jenner by Casey Cadwallader, the creative director of Mugler himself, and is a vision of asymmetrical lace.

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Kylie Jenner in Paris in September 2022

Jenner is a big proponent of the underwear-as-outerwear trend. With a pair of white hipster briefs, a matching tank top, black tights disappearing into black boots, and a grey overcoat as her top layer, it’s simple yet showstopping.

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Kylie Jenner at the Balmain Show at Paris Fashion Week in September 2022

It pays to have friends in high places — in this case, designer friends who can create looks for you and only you. Jenner’s been a muse to designers plenty of times, but this crochet minidress constructed by Balmain’s Olivier Rusteing makes our top five.

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Kylie Jenner in L.A. in March 2021

Is it a coincidence that Jenner stepped out in an eerily similar outfit to the one she wore to celebrate the Haqq sisters’ birthday in 2023 back in 2021, to the same venue? The only difference is her color palette: Red instead of black. Proof even celebrities are outfit repeaters (kind of).

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Kylie Jenner at the ‘Vanity Fair’ Oscar Party in 2021

This mermaid-style gown from Ralph and Russo marries the fun of sparkles with Old Hollywood glamour. Jenner said the look was worth it, even if she had trouble sitting down whilst wearing the ensemble.

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Sophisticated Sexy

For the premiere of Travis Scott: Look Mom I Can Fly, Jenner opted for an outfit that was pure sophistication. The white bodycon dress nodded to her signature curve-enhancing aesthetic, but the dress also boasts some sexy back cutouts — and we loved the addition of the bow choker accessory.

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Kylie Jenner at the Met Gala in 2019

Once upon a time, Jenner also went through a purple stage. She brought her once-signature hue back for the 2019 Met Gala, and perfectly nailed the “Camp: Notes on Fashion” theme.

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Kylie Jenner at the Grammy Awards in 2019

Balmain suits Jenner well. Case in point: this blush pink jumpsuit with dramatic sleeves, worn to the Grammys. We imagine the one-and-done item is as comfy as it is pretty; it’s different from the celeb’s usual body-hugging dresses, but we’re here for it.

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Kylie Jenner in N.Y.C. in November 2018

Why wear denim-on-denim via separates when you can achieve the Canadian Tuxedo look with one sleek jumpsuit? This all-jeans-everything number is one we can get behind.

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Kylie Jenner at the MTV VMAs in 2018

We don’t need to tell you the business owner and founder is a boss; we’ll let this sharp blazer dress ensemble tell you instead.

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Kylie Jenner in L.A. in August 2018

The Kardashian-Jenners love a Barbie moment, and Kylie is, clearly, no exception. We don’t know what we love most about this fit — the dress, the shoes, or the platinum ponytail.

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