You don’t have to be a street style star—or a first lady—to wear the hell out of a pillbox hat.
XNY/Star Max
All products featured on Glamour are independently selected by our editors. However, we may receive compensation from retailers and/or from purchases of products through these links.
Jennifer Lawrence makes the biggest fashion risks look like a walk in the park…or perhaps we should say a walk in Manhattan.
Sure, we all know monochrome brown ensembles are taking over the New York City streets where the all-black uniform once reigned supreme, but the true star of fall 2025 has to be unique accessories, from animal-print booties to oversized scarves to tiny statement hats. The best thing about these micro trends is that they don’t spark an annual outfit overhaul, instead allowing you to hunt for one or two delightful pieces that will work with the basics you’ve already got.
Take Jennifer Lawrence’s latest look, for example. The foundation couldn’t be more simple and comfortable for a mom on the go, from her chunky black clogs and soft black pants—which may or may not be sweats—to her white T-shirt and oversized olive wool coat. However, she instantly turned the coffee-run ’fit into a street style moment with a vibrant double-sided striped scarf and the true star of the look: a tiny felt leopard-print hat.

Backgrid
In many ways the pillbox hat is the perfect winter successor to the crochet skullcaps that were all over Copenhagen Fashion Week this August. While those head coverings reference the ’70s in a fresh and playful way, Lawrence is putting a modern spin on a glamorous piece from the ’50s and ’60s, instantly evoking the elegance of first lady Jacqueline Kennedy with none of the usual pomp and circumstance—and she’s not the only one.
In Berlin on October 31
Jeremy Moeller/Getty Images
During Paris Fashion Week on October 2, 2025
Moritz Scholz/Getty Images
During Paris Fashion Week on October 3, 2025
Jeremy Moeller/Getty Images
During Paris Fashion Week on October 01, 2025
Raimonda Kulikauskiene/Getty Images
Pillbox hats, newsboy caps, berets, and small felt hats are cropping up all over ad campaigns, runways, and in the street style photos of the most fashionable women on social media. Any of these vintage-inspired caps add an element of whimsy to even the most demure look, so imagine the fun that can be had when you turn up the volume with color and print, à la J.Law.
And if you pair it with your most favored basics, as Jennifer Lawrence did, you don’t have to expel much energy at all to be the chicest woman in the grocery store.
Lawliet Pillbox Hat
By Anthropologie Faux-Fur Animal-Print Cloche Hat
Emily Tannenbaum is a contributing editor for Glamour, covering Hollywood, television, movies, and culture. She’s been featured as an expert on BBC World News, while her profiles, reviews, and recaps have been published by Glamour, Elle, Cosmopolitan, Vanity Fair, Variety, and IGN. You can find her on Instagram at @ectannenbaum. … Read More
