Kendall Jenner Adds Flirty Twist to Toy Story Halloween Look

Kendall Jenner turned heads this Halloween with a bold reinterpretation of Jessie from “Toy Story.” The supermodel’s costume featured signature cowboy elements with a modern, cheeky twist. Jenner wore a cropped white-and-yellow shirt and black-and-white pants with denim accents — both modified with front and back cutouts. The look was completed with a braided wig and red cowboy hat. Her outfit quickly went viral, sparking fan reactions across social media.

Kendall Jenner debuted her 2025 Halloween costume on October 31 at a private celebrity event in Los Angeles. She dressed as Jessie from Pixar’s “Toy Story,” but added a flirty spin with strategic cutouts and a cropped top. The outfit was designed to blend nostalgia with high fashion, drawing attention for its bold styling. Jenner’s costume was shared widely online, with fans praising her creativity and confidence.

Costume Breakdown and Styling

Jenner’s ensemble included:

• Cropped white-and-yellow cowboy shirt
• Black-and-white cow-print pants with denim trim and cutouts
• Brown belt, braided auburn wig, and red cowboy hat

The outfit paid homage to Jessie’s animated look while incorporating runway-ready modifications. The cutouts added a daring edge, aligning with Jenner’s reputation for fashion-forward Halloween choices.

Fan Buzz and Industry Commentary

Fashion insiders noted Jenner’s ability to balance character accuracy with personal flair. “She knows how to elevate a costume into a statement,” one stylist told RealityTea. Fans flooded Instagram with comments like “iconic,” “best costume of the year,” and “Jessie never looked so fierce.” TheFashionSpot called the look “a cheeky remix of a childhood favorite.”

Cultural and Style Influence

Jenner’s costume has already influenced Halloween trends, with similar Jessie-inspired outfits appearing across TikTok and Pinterest. Analysts say her look reinforces the growing popularity of nostalgic characters reimagined through a high-fashion lens. The post also boosted engagement across Jenner’s social platforms, with millions of likes and shares.

What’s Next: Upcoming Appearances and Fashion Drops

Jenner is expected to attend the Vogue Fashion Gala later this month, where she may debut another themed look. Her Halloween outfit could inspire future capsule collections or collaborations, especially with brands targeting Gen Z nostalgia. No official announcements have been made yet.