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Kendall Jenner Is the Most Convincing Life-Size Jessie From ‘Toy Story’ We’ve Ever Seen

The model embraced her cowgirl side and rocked her fan-favorite red hair this Halloween.

Ananya Panchal

Kendall Jenner is seen arriving at Ristorante Puny in Portofino, Italy. 

Kendall Jenner is a horse girl at heart. She also rocks red hair. The stars aligned this Halloween and the supermodel dressed up as the red-haired cowgirl Jessie from Toy Story. And the perfectly-executed look, professionally photographed by Adrian Martin, will go down in history as one of the most memorable celeb Halloween costumes. 

“Well aren’t you just the sweetest space toy,” she captioned the carousel post in which she poses in front of the classic blue sky and perfect clouds that are the background of every Toy Story film cover.

Jenner wore a cropped version of Jessie’s white and yellow collared button-down shirt and cheeky denim high-waisted bikini-style bottoms above cow-printed chaps that reached mid-thigh. She obviously topped it off with Jessie’s big red cowboy hat and let her hair hang in two braids.

The look was created by stylist Dani Michelle and Jenner’s hair was done by Jen Atkin.

Several of Jenner’s A-list celeb friends piped up in the comments saying how much they loved the look.

“So good!” wrote Gigi Hadid, while Lily Aldridge said “Cutieeeee.” Big sis Khloe Kardashian chimed in with “Awwwwwwwwww my baby.”

Others were not as pleased with the costume. Several trolls accused Jenner of “sexualizing” an animated character and “ruining” a children’s movie.

The 26-year-old reality TV star opted for a more comfortable look at the Halloween party she attended. Her makeup artist, Mary Phillips, posted a photo of Jenner’s transformed look, which featured a bandeau style top and Jenners natural dark brown hair, still in braids. Her glam was kept natural with a heavy rosy blush.

“Cutest cowgirl there ever was @kendalljenner,” Phillips captioned her up close and personal post of the makeup look. “She won Halloween.”

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Ananya Panchal

ANANYA PANCHAL

Ananya Panchal is a NYC-based Lifestyle & Trending News writer at SI Swimsuit. Before joining the Swim team, the Boston University Alum worked for culture & entertainment beats at Bustle, The San Francisco Chronicle and the TODAY Show. When Ananya is not writing or doom-scrolling on social media, she can be found playing sudoku, rewatching One Tree Hill or trying new restaurants. She's also a coffee and chocolate (separately) enthusiast.