Raise your hand if you’re a millennial who once had a well-rounded collection of newsboy caps. For this fashion writer, that assortment included embellished styles from Limited Too. Then, when I entered high school, my rotation got a bit more sophisticated (or sophisticated for a teenager, that is), with the majority of looks — faux leather, herringbone print, etc. — hailing from Free People or Urban Outfitters. But much like every trend, it eventually vanished from the fashion scene. Well, up until recently. It’s time to dig them back up, seeing as celebrities have deemed the notoriously grandpa-looking silhouette chic in 2025. Yes, ready or not, all signs point to a newsboy cap revival.
“With the return of the aughts and Y2K styling, it only makes sense that the newsboy cap is resurfacing,” explains Anthropologie’s head of styling, Kyla Flax. The expert points to Sarah Jessica Parker’s iconic character, Carrie Bradshaw, in Sex and the City, as one proponent of the hat. According to Flax, Carrie styled her pairs in “cheeky, mismatched ways.” And who could forget the tweed styles Andy Sachs, portrayed by Anne Hathaway, wore in The Devil Wears Prada?
Meanwhile, according to namesake designer Eugenia Kim, stars like Christina Aguilera, Britney Spears, and Gwen Stefani rocked her brand’s iterations, oftentimes pairing the hats with their 7 For All Mankind jeans. “Everyone is celebrating and referencing the early aughts but through a modern filter that is less literal,” the brand founder tells TZR.
Now, Hollywood’s newest generation of darlings is adopting the newsboy cap look, which was first worn by men in the late 19th and early 20th centuries. Last month, Kendall Jenner stepped out in New York City, wearing a black tweed iteration with a brown suede jacket and dark gray fringe scarf. Back in January, Keke Palmer donned a dark gray leather style from Wolford. The actor wore the hat with a plaid ensemble from Schiaparelli’s Fall/Winter 2024 collection and knee-high leather boots.
Powerhouse designers are bringing back the silhouette as well. Chanel’s Pre-Fall 2024 show line featured a variety of colorful tweed newsboy caps (Penélope Cruz took a pink one for a spin shortly after they hit the runway). Then, on Prada’s Fall/Winter 2024 catwalk, the hat was a key element of the collection, coming in styles that ran the gamut from feathered iterations to suede hats. Most recently, for its Fall/Winter 2025 show at NYFW last month, Khaite debuted a sleek black newsboy cap, showing the piece in 15 looks.
Ahead, learn how to work a newsboy cap into your wardrobe with five outfit ideas. This is just the beginning of the silhouette’s resurgence.
Try A Cohesive Palette
The hat may feel less intimating to wear if you sport it alongside pieces in a similar color palette. For instance, this fashion girl paired her brown style with a belted coat and fringe bag in near-identical shades.
Go For Glamour
If you’re someone who lives for a glamorous outfit moment, team your newsboy cap with a feather or sequin-adorned miniskirt. You’re sure to make quite the entrance on your next Friday out on the town.
Slip Into Slouchy Silhouettes
Because a newsboy cap is decidedly a statement-maker, consider keeping your outfit understated. This model off-duty-approved white tee and baggy jeans look is an excellent option for a casual weekend out and about.
Bring Your Accessories A-Game
Flax loves a newsboy cap styled with a hint of novelty. “Lean into scarves, belts, and bag charms to really finish the look,” she recommends. Take notes from this street style star and incorporate leather gloves into the outfit on these final cold winter days.
Lean Into Leather
Should you be concerned about your look veering into Y2K territory, try a full leather outfit — like this quilted jacket and shorts combo above. Suede knee-high boots will only elevate the ensemble.