Celebrity Style

Kendall Jenner Is The New Face Of This Y2K It Bag

I’m sat.

by Alyssa Lapid
Kendall Jenner seen in Financial District on September 13, 2025 in New York City.
Aeon/GC Images/Getty Images
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One of the biggest icons of the early aughts is officially back — and I’m not talking about a Y2K it girl. I’m actually referring to an it bag, particularly the Chloé Paddington. Once a mainstay on the arms of Kate Moss, Jennifer Lopez, and Sienna Miller, the carryall became inextricably linked with the free-spirited DNA of the French label.

While interest in the earthy and dreamy aesthetic dipped, it’s poised to return as one of the biggest style movements in the coming years, thanks, in no small part, to Chloé’s new creative director, Chemena Kamali, who debuted her first collection for the brand in March 2024 to rousing success. Later, during the brand’s Fall/Winter 2025 Paris Fashion Week show, she made even more waves when she reintroduced the Paddington.

For months, the fashion cognoscenti correctly guessed that the bag’s official relaunch would be accompanied by a star-studded campaign. No one, however, could’ve imagined which celebrity the label would tap: Kendall Jenner.

Kendall’s Chloé Campaign

On Wednesday, Sept. 24, the supermodel was announced as one of the faces of the new Paddington, alongside White Lotus’ Aimee Lou Wood and Meovv K-pop singer Anna. In the campaign, photographed by David Sims, Jenner posed in a white ruffled top with lace trim details on its sleeves, around the empire waist, the hem, and the plunging neckline.

Despite her typically minimalist nature, Jenner’s look was uncharacteristically flouncy, which was a welcome change. (Her younger sis, Kylie, has also been spotted trading her bodycon go-tos for Chloé’s romantic options.)

Courtesy of Chloé

For a casual look, she paired the top with high-waist jeans.

Courtesy of Chloé

Shop The Bag

The pièce de résistance of the outfit, of course, was her carryall: a black east-west style bag characterized by its large padlock, aka the signature Paddington emblem. Originally designed by Phoebe Philo in 2005, Kamali’s version features lighter hardware, a single-zip opening, and adjusted shoulder straps. Oh, ICYWW, the padlock is functional.

If, like me, you’ve had this bag on your wishlist for a while, it’s officially available to shop at Chloé stores and on site for $2,750, and is available in hues such as black, cream, moss, navy, and brown.

I’m all for this fashion déjà vu.

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