From a yellow Teletubby to Pamela Anderson's leather-clad Barb Wire look, Kendall Jenner's costume history is basically a fashion time machine.
People published a retrospective on Oct. 31, 2026, rounding up Kendall Jenner's Halloween costumes through the years, pulling together 22 looks that stretch from 1998 all the way to 2024. The list shows how Jenner turned childhood dress-up into full-blown fashion moments, often alongside sister Kylie Jenner, best friend Hailey Bieber, and model Cara Delevingne.
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How Kendall Jenner's Halloween costumes evolved from childhood to high fashion
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The earliest entry dates back to 1998, when a very young Kendall dressed as Laa-Laa, the yellow Teletubby, while baby Kylie wore a Po costume. A year later, the sisters leaned into movie magic, recreating The Wizard of Oz. Kendall became the Wicked Witch of the West in a black dress, oversized witch hat and green face paint, while Kylie played Dorothy. Jenner actually revisited that exact look years later, posting a throwback clip of the witch costume on Instagram in 2019.
Another early costume shows Kendall and Kylie as pirates, standing next to their mom, Kris Jenner. Kendall wore a red-and-black striped shirt with a skull-and-crossbones design, paired with red pants and a matching scarf. These childhood photos set the tone for what would become a yearly tradition of dressing up as something recognizable, then making it entirely her own.
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Kendall Jenner Halloween costumes turn pop culture icons into runway moments
As Jenner's modeling career took off, her costumes started doing double duty as fashion statements. In 2014, she and Cara Delevingne showed up to Adam Lambert's Halloween party dressed as Mario and Luigi, complete with character hats and fake mustaches. By 2017, Jenner was Buttercup from The Powerpuff Girls in a custom Bryan Hearns outfit that included a green-and-black striped bra, a ripped denim miniskirt and thigh-high fishnet stockings. Hailey Bieber stood right beside her as Bubbles, proving these two have been Halloween partners for years.
2018 turned into a two-costume year. Jenner and her sisters Kourtney, Kim and Khloé all wore borrowed Victoria's Secret lingerie and oversized wings for one shoot. Then at the Casamigos Halloween party at Catch Las Vegas inside the ARIA Resort & Casino, Jenner showed up as an Austin Powers fembot, wearing a sheer pink slip dress, pink gloves and a huge blonde wig. It's one of the costumes fans still bring up whenever Kendall Jenner's Halloween costumes through the years get discussed online.
The Pamela Anderson, Jessie and Marilyn Monroe years define recent Halloweens
Jenner's 2020 costume might be the boldest on the list. While celebrating her 25th birthday with a Halloween-themed party, she channeled Pamela Anderson's character from the 1996 film Barb Wire, pulling on a blonde wig and a leather leotard to match the look exactly. Two years later, in 2022, she went in a completely different direction, dressing as Jessie from Pixar's Toy Story, but gave the cartoon cowgirl a grown-up makeover with a crop top, short shorts and cow-print chaps.
In 2023, Jenner channeled old Hollywood glamour as Marilyn Monroe, wearing an Intimissimi turtleneck with platinum-blonde curls styled to match the screen icon. Each costume kept the core idea of the character recognizable while adding Jenner's own high-fashion spin, which is exactly why these looks keep getting recirculated every October.
Kendall Jenner and Hailey Bieber's 2024 costume closes out the list
The most recent dated costume in the People feature comes from 2024, when Jenner and Bieber recreated the public image of Paris Hilton and Nicole Richie from The Simple Life. The pair leaned into denim-heavy, early-2000s styling to match the reality TV duo's signature look, tapping into the current wave of Y2K nostalgia that has been showing up across fashion and pop culture.
It wasn't the first time Jenner and Bieber teamed up for Halloween, either. Their 2017 Powerpuff Girls pairing already proved the two work well together when it comes to coordinated costumes, and the Simple Life recreation gave fans another matching moment seven years later.
Why this Halloween costume history keeps resurfacing every year
Part of what makes this retrospective so shareable is the mix of nostalgia and glamour. Jenner's costumes rarely rely on store-bought outfits or simple face paint. Instead, they're treated like editorial shoots, with wigs, custom pieces and professional photography turning a holiday costume into content people still talk about years later.
The People article doesn't name one single best costume, but the Pamela Anderson, Austin Powers, Jessie and Marilyn Monroe looks are the ones most often repeated across fashion coverage. With Jenner's track record of either reviving a solo character or teaming up with Kylie, Bieber or Delevingne, it's likely future Halloweens will add new entries to this growing list.
