Kylie Jenner’s 2014 Chanel Chelsea Boot Moment: A Blueprint for Edgy Street Style

Long before the era of minimalist “quiet luxury,” Kylie Jenner established her fashion identity through a moody, high-low aesthetic that remains a blueprint for urban street style.

On January 31, 2014, in Los Angeles, Jenner provided a masterclass in transitional dressing, balancing feminine silhouettes with rugged, designer hardware.

Kylie Jenner steps out in Los Angeles wearing black Chanel leather Chelsea boots, grounding her draped wrap skirt and quilted biker jacket with a polished, utilitarian finish

Stepping out in a Free People ruched asymmetrical skirt and a quilted Topshop biker jacket, the ensemble highlighted her ability to mix accessible fast-fashion with luxury staples like the Balenciaga bowling bag.

The chunky silhouette of Kylie Jenner’s Chanel Chelsea boots adds weight and balance to her otherwise fluid, asymmetrical street-style ensemble in Los Angeles, California, on January 31, 2014 (Credit: WENN)

However, the true focal point was her footwear: a pair of Chanel leather Chelsea boots. These boots, characterized by their pull-on design and masculine silhouette, anchored the airy texture of her wrap skirt, proving that a solid investment boot is the ultimate wardrobe stabilizer.

Whether you’re looking to replicate this timeless, edgy aesthetic or seeking a versatile designer alternative, this look remains a primary reference for “city chic” styling.

A closer look at Kylie Jenner’s Chanel pull-on Chelsea boots reveals their smooth leather upper, elastic side panels, and low stacked heel designed for all-day wear

Chelsea boots — whether classic Chanel or bold street-ready styles — have been a celebrity favorite across countless fashion moments on Your Next Shoes. From Rita Ora rocking Chanel boots after Paris Fashion Week to Kristen Stewart’s edgy Chanel combat-boot edit at Chanel shows, stars keep returning to sturdy yet chic ankle boots.

You’ll also find Chelsea boots in our broader Chelsea boot style guide, where we spotlight looks from icons like Kendall Jenner’s polished Chelsea moments, as well as styling tips that prove these boots are forever — from streetwear to elevated off-duty silhouettes.

Even though Kylie had a very distinct personal style, we couldn’t help but notice how much she was beginning to look like her older half-sister Khloe!

The rounded toe and sturdy sole of Kylie Jenner’s Chanel ankle boots emphasize their practical, menswear-inspired appeal

Not surprisingly, her Chanel boots come with an insane price tag of well over $1,200 at retail—though you can occasionally find them on the resale market for between $600 and $900, depending on their condition.

Chanel pull-on leather Chelsea ankle boots, featuring elastic gussets, a lugged sole, and a timeless black leather finish

From Street Style Staples to High-Glam Heels

This early Chanel Chelsea boot moment captures the foundation of Kylie Jenner’s evolving footwear identity — grounded, directional, and quietly influential.

From practical ankle boots that anchored her off-duty looks to sculptural heels and couture mules on the red carpet, her shoe choices have consistently shaped her fashion narrative. Explore more of Kylie Jenner’s defining shoe and fashion moments below.