Make Sure Flaunting a Pillbox Hat on a Regular Basis Tops Your List of New Year’s Resolutions

Fashion has a history of repeating itself. Practically every decade has experienced some kind of recent resurgence, from the 80s to the 2010s. (Although the latter admittedly seems like only yesterday.) Now a blast from the past is taking a major sartorial foothold in 2025 and, most likely, beyond. Pillbox hats were spotted on the Fall 2025 runways and their popularity is only expected to expand.

Jackie Kennedy is synonymous with the style as the fashionable first lady was often seen topping off her outfits with the brimless, straight-sided and flat-top toppers. Now legendary designer Roy Halston Frowick made a name for himself with the version he designed for her to wear at her husband’s inauguration. According to CNN, the now coveted shape was not at all intended. Halston actually crafted the chapeau into a dome, but thanks to the high winds on that historic day, the soon-to-be first lady, in an effort to secure the hat, accidentally gave it a noticeable dent.

Obviously, Altuzarra and Alaïa fully intended to replicate the boxier silhouette. Altuzarra’s is thicker, while Alaïa’s is sleeker, almost otherworldly. Other big-name fashion brands are also championing the toppers. Chloe’s Toque hat more closely resembles Altuzarra’s stacked vibe. If you’re wondering if you can pull off the look in winter without freezing, Loro Piana’s Jasmine Rabbit Hair Felt Pillbox Hat will keep you nice and toasty.

Since the Fall 2025 shows were all the way back in February 2025, the trend has had plenty of time to trickle down to the masses. The mass retailers that is. One of our favorite takes is actually from über affordable retailer H&M. Its wool hat in a delectable dark brown hue looks way more expensive than its under $40 price tag indicates. The Frankie Shop’s versions boast a curved crown because in 2025 and 2026, it’s OK to slightly bend the rules in addition to the hats. COS’ Sculpted Wool Beret falls into this category, too. The creamy creation comes in at $99. Then there’s Lele Sadoughi’s offering that actually blends a beret with the traditional pillbox structure for $145. Add a bit more mystique by opting for numbers with attached veils, like the GTM x L’AGENCE Anstine Pillbox Hat.

Consider this your official sign to take pillbox hats out for a seasonal spin. Shop the best ones below.