Kendall Jenner Pulled A Newsboy Cap Straight Out Of Her 2016 Closet

Even though Kendall Jenner has only walked in one New York Fashion Week show so far this season, she’s still booked and busy. On Feb. 7, the model dominated Veronica Leoni's inaugural Calvin Klein presentation — the label’s first show since 2018. In the days since, she’s skipped the Fall/Winter 2025 catwalk, and instead upped her street style appearances. Most recently, in the West Village on Feb. 10, Jenner approved the divisive newsboy cap resurgence, alongside an equally retro-inspired ensemble. And now that the multi-hyphenate pulled it off, it’s only a matter of time before her fellow it girls follow suit.

After lunch at Saint Ambrose, an Italian hotspot in the heart of the West Village, Jenner was snapped by the paparazzi in nostalgic numbers galore. All eyes went to her black felted newsboy, complete with a short, stiff brim, and a broad, slouchy crown. The cap looked chic next to her corseted suede jacket. She buttoned the tan topper up completely, and layered a tasseled brown scarf overtop for extra warmth. From there, the 818 founder slipped on black straight-leg jeans. Then, Jenner paired her go-to loafers from The Row with stark white socks. She also sourced The Row for the celeb-approved Nuance Hobo Bag in brown leather. Instead of lots of jewelry, Jenner completed her cool co-ord with oval-shaped sunglasses and micro-mini hoop earrings.

Jenner doesn’t wear headpieces very often, so why the newsboy, you ask? Well, perhaps she was inspired by other fashion muses, including Keke Palmer, Salma Hayek, Kelly Rowland, and Anne Hathaway (to name a few), who have worn the conversation-starter recently. Or, maybe Jenner took cues from her own rotation. Nearly 10 years ago, the A-lister frequently donned the cap during laidback occasions. In July 2016, she was spotted at LAX in a black version, low-rise skinny jeans, and a cropped leather jacket. A year later, Jenner chose an off-white newsboy, decorated with a braided band around the crown. She styled it once again with skinny jeans, a white T-shirt, and an elongated cardigan.

All this to say? Jenner and newsboys go way back. So, don’t be surprised if her cap makes another appearance this fashion month.