Kendall Jenner and Hailey Bieber Wear Winter Style Two Ways While on a Night Out in NYC

Kendall Jenner and Hailey Bieber stepped out together in New York City for a night out, and took two different approaches to dressing. The model and the Rhode beauty founder embraced winter style in their own ways while out to dinner at Café Zaffri at The Twenty Two.

Kendall and Hailey, who were joined by Justin Bieber, J Balvin and his girlfriend Valentina Ferrer, each embraced skirts with sheer black tights. While Hailey wore a pinstriped set — adding another entry to the skirt suit trend — Jenner embraced an avant-garde silhouette in a white fur peplum jacket with oversized shoulders and a wide lapel by Phoebe Philo.

Jenner’s coat hails from Philo’s “collection B,” which was revealed in October of 2024, and is part of the designer’s goal to create clothing and accessories “rooted in exceptional quality and design.” Dubbed “The Teddy Jacket,” the coat is sculpted out of cashmere shearling and lined with silk. Jenner paired it with a mini skirt and a pair of pumps with an angular geometric heel. She accessorized with a pair of gold huggie hoop earrings.

Meanwhile Hailey put her stamp on business attire in a tailored plunging skirt suit. She paired the ensemble with pointed-toe heels and oval sunglasses. The look was a continuation of the dark glamour approach she took to winter dressing last weekend, while out with Justin in New York City. For the occasion Hailey wore a monochromatic ensemble consisting of a black sweater with a center seam and a pair of wide-leg trousers elongated with pointed-toe black boots. She topped her look with a cropped fur jacket, pair of sunglasses, a slouchy leather bag, and her oval-cut diamond engagement ring.

Kendall, who recently walked in Schiaparelli’s spring 2025 haute couture fashion show in Paris, made her return to the NYFW runway on Friday at Calvin Klein’s fall 2025 show. The presentation, which marked the brand’s first NYFW show since 2018, saw Kendall wearing a pinstripe coat with square-toe slingback flats and a pair of gold aviator glasses.