Kylie Jenner may be known for her glamorous red-carpet gowns and head-turning street style, but she often proves that nothing beats the effortless cool of a classic sneaker.
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In both late 2015 and early 2016, the youngest Jenner stepped out in Los Angeles wearing Converse—once in a luxe designer collab and again in the timeless Chuck Taylors.
These two casual outings demonstrate how Kylie seamlessly blends laid-back staples with high-fashion accessories, transforming everyday errands into moments worth noting for their style.
Off-Duty Edge: Kylie Jenner Revisits Classic Chuck Taylors in Los Angeles
In April 2016, the youngest Jenner, taking a cue from her older sister, Kendall Jenner, visited Restoration Hardware Modern in Los Angeles to shop for furniture with her friend, Hailey Baldwin.
Kylie Jenner kept her look casual-chic in a vintage-inspired Von Dutch jacket and oversized sunglasses for a visit to the Restoration Hardware Contemporary Art Gallery on April 13, 2016, in Los Angeles (Credit: WENN)
Kylie went full-out with her makeup, but she uncharacteristically chose to dress down for the day.
She balanced the boxy jacket with sleek leather J Brand skinnies and her go-to Converse high-tops
She wore a pair of skinny leather jeans by J Brand and a plain white tee hidden under a shapeless Von Dutch jacket.
A close-up of her well-worn Chuck Taylor All Stars proves their timeless appeal in off-duty dressing
The then-18-year-old styled her casual outfit with a pair of Chuck Taylor Converse “All-Star” high-top sneakers and added a touch of luxury to her look with an Hermès tote.
Kylie later shared a mirror selfie from inside Restoration Hardware, accessorizing her sneakers-and-jacket look with a luxe Hermès tote (Credit: Kylie Jenner’s Instagram)
Kylie ignored a paparazzo’s question about wedding plans with Tyga as she entered the building.
Kylie made her way down the gallery steps in her black Converse high-tops, pairing them with sleek leather skinnies for an effortlessly cool finish
You can order these no-fail iconic Chuck Taylor Converse “All-Star” shoes at Zappos and Nordstrom.
Created in 1917, the Chuck Taylor All Star sneaker was the original basketball shoe
Chuck Taylor Converse “All-Star” High Top Sneakers, $60 – $85
A few months earlier, Kylie had already proven her love for Converse during a December 2015 shopping trip in Los Angeles.
Streetwear Luxe: Kylie Jenner Rocks CDG × Converse on a Los Angeles Shopping Trip
Despite paparazzi questions and the usual media frenzy, she kept her calm—and her sneakers front and center—in another effortlessly casual look.
Kylie kept it sleek in an all-black Acne Studios biker jacket layered over a cropped turtleneck
Kylie was spotted having lunch at Le Pain Quotidien before hitting up a jewelry store and Barneys New York. The paparazzi followed her around, throwing out random, mean questions, presumably to rile up the young Jenner.
She paired faux leather joggers with high-top sneakers for a streetwear-meets-luxury vibe in Los Angeles on December 16, 2015
Kylie, on the other hand, remained composed in her all-black ensemble. The 18-year-old wore a cropped turtleneck top with loose black pants and a leather jacket from Acne Studios.
A close-up reveals the playful red heart motif from the Comme des Garçons x Converse collaboration
CDG × Converse: The Playful Heart Logo That Redefined a Classic
Kylie finished off her look with oversized Dior sunglasses and a pair of high-cut sneakers from the Comme des Garçons Play x Converse collaboration—one of the most enduring and recognizable partnerships in modern fashion.
Launched in 2009, the collab took the universally loved Converse silhouette and gave it a high-fashion twist with Comme des Garçons’ playful edge.
The sneakers are instantly recognizable thanks to the bright red heart-and-eyes logo, designed by New York artist Filip Pagowski, which peeks out from the canvas upper. Available in both high- and low-top versions, the shoes typically adhere to timeless black or white colorways, but the quirky logo detail elevates them far beyond the average Chuck Taylor.
The back view showed how the statement sneakers grounded her monochrome look with a subtle pop of detail
Explore More Comme des Garçons Sneaker Style
Kylie isn’t the only star turning to Comme des Garçons collaborations for standout looks. From streetwear guides to bold red-carpet moments, these YNS features highlight how CDG’s sneaker influence continues to shape fashion culture:
👟 YNS & CDG / Sneaker × Fashion Features
- 🧥 Streetwear’s Next Wave: The 14 Brands Shaping the Future of Fashion — a broader look at brands (including CDG) that define sneaker and street-style culture.
- 🎸 Miley Cyrus Channels Bangerz-Era Rebellion in Comme des Garçons Platform Sneakers — Miley merges retro punk and design sneakers in a bold statement outfit.
- 💑 Best Matching Shoes for Couples: Including Comme des Garçons × Converse — a style guide recommending CDG × Converse as a standout pick for sneaker coordination.
- ⬆️ Poppy’s Bold Platform Moment in Comme des Garçons × Nike Striped Sneakers — showing how CDG’s collaborative sneaker energy extends beyond Converse into bold, statement-making designs.
Unlike standard All Stars, the CDG editions are built on the Chuck 70, a premium version of the original that uses thicker canvas, vintage-inspired detailing, and enhanced cushioning for comfort.
Over the years, the line has introduced variations such as multi-heart prints, red-sole editions, and occasional reinterpretations of other Converse models, including the Jack Purcell and One Star.
Comme des Garçons x Converse Chuck Taylor PLAY – Hidden Heart High Top Sneaker in Black Canvas, $120 – $125
Comme des Garçons x Converse Chuck Taylor PLAY – Hidden Heart High Top Sneaker in White Canvas, $120 – $125
More Converse Celebrity Style Moments
From Kylie Jenner’s streetwear essentials to other A-listers’ off-duty staples, Converse sneakers remain a timeless go-to in celebrity fashion. Explore more style inspiration below:
👟 YourNextShoes & Converse / Sneaker Editorial Highlights:
- ✨ Jessica Alba Shows Off Casual Street Style in Ripped Jeans and Converse Sneakers — Jessica pairs metallic Converse low-tops with distressed denim for a relaxed off-duty look.
- 🎬 Fierce in Chuck Taylors: Jennifer Lopez Films Shades of Blue in Undercover Chic Look — J.Lo styles classic white Chuck Taylors with cuffed jeans and a blazer during filming.
- ❤️ From Denim to Dresses: Emma Roberts Proves Red Converse Go With Everything — Emma demonstrates the styling versatility of red Chucks with both denim and bold skirts.
- 💡 How Amber Rose Styles High-Top Converse With Leggings — A streetwear approach showing how to balance sporty high-tops with sleek leggings.