Among the 1960s-inspired silhouettes and accessories this ready-to-wear season was a reprisal of a retro relic: the pillbox hat. Learn more about the history of Jacqueline Kennedy’s favorite chapeau — and how I styled an all-black look with nods to the early 60s.

The ‘60s Pillbox Hat: How to Style This Year’s Biggest Accessory Trend

Among the 1960s-inspired silhouettes and accessories this ready-to-wear season was a reprisal of a retro relic: the pillbox hat. Learn more about the history of Jacqueline Kennedy’s favorite chapeau — and how I styled an all-black look with nods to the early 60s.
April 12, 2025
article by Mari Alexander/

photography by Lika Khomeriki

There seems to be a consensus that when it comes to statement accessories this year, nothing really tops the pillbox hat.

It was the style du jour everywhere — on the runways and the streets, and at fashion week events and parties. Now, I’ll preface this by saying that headwear isn’t particularly uncommon to spot during the fall-winter season. From bonnets to balaclavas, the fashion crowd always finds cool ways to keep their heads warm. But the pillbox hat is what looked newest (or oldest, however you want to look at it) and seemed to reinforce the palpable aura of the early 1960s that suffused many of the shows I attended. That’s why I had to take a closer look.

First things first: What exactly is a pillbox hat? Small and rounded, a pillbox hat is a brimless, typically flat-topped hat that sits snugly at an angle on the head. It became especially famous in the 1960s — largely thanks to Jacqueline Kennedy, who wore the hat at her husband’s inauguration in 1961. In fact, she was such a fan of pillbox hats, she practically became synonymous with the style. (The design worked for the first lady, in part, because it preserves her perfectly styled hair.) Behind the hat was none other than the great American designer Halston.

AboveLace was another oft-seen fabric on the runway — an emblem of femininity, grace, and romance.

It just so happened that I recently started reading Simply Halston: The Untold Story by Steven Gaines — an in-depth biography about the iconic fashion designer’s life and work. (Netflix’s five-episode mini-series, Halston, is based on this book.) Halston was, by all accounts and measures, one of the most prolific designers who brought American fashion to its apogee. His accomplishments were many. Halston was one of the first to embrace high-end, ready-to-wear collections, making luxury fashion more accessible. He popularized Ultrasuede fabric and created a successful line of fragrances, eyewear, and home goods. And yes, he designed Jacqueline Kennedy’s pillbox hats — but he didn’t invent them. 

“Like almost everything in fashion, it was an idea borrowed, some say from Balenciaga, others from Christian Dior, who had shown dozens of pillbox-shaped hats in collections that hundreds of designers had witnessed over the years,” writes the biographer. It’s happened again, which is no surprise, as fashion’s been rummaging through the decades for inspiration with more vigor than ever. The past few years have been rife with midriff-baring millennium kitsch, and while I’ll admit that was a boatload of fun, seeing this elegant relic from a bygone era is somewhat of a nice change — in my humble opinion

Maybe it’s because the ‘60s is a decade I didn’t get to experience, so there’s still a lot to mine and discover. Whatever the reason, I loved seeing this style revival on runways across the world. For example, Emilia Wickstead sent sleek, round chapeaus that finished off several prim, early ‘60s-inspired looks. As did New York-based Vaquera, which embellished the style with oversized bows. At Danish brand Herskind’s Copenhagen Fashion Week showing, a host of models stepped out with tall, oversized pillbox hats, and at Cmmn Swdn, the accessory was given height and volume with fur. 

The list goes on. 

It looked très chic on the runways, and I couldn’t wait to put my own spin on the trend. Anchoring the look was a classic, black pillbox hat by Gigi Burris. The New York-based milliner is a former CFDA/Vogue Fashion Fund finalist — and for good reason. She brings exquisite craftsmanship to her products, all of which are made by hand. The pillbox hat’s textured finish gives it a substantial feel, and I wanted to balance that with something a little more delicate.

On the leftA wool-lace-wool formula informed this look, tempering heavy textures with lace.

This see-through top, with its padded shoulders and above-the-elbow sleeves, felt like the right vintage-inspired move. Then, I pulled a trusty favorite — a pair of  The Frankie Shop wool pants — from the closet and wore it high on the waist. Again, for that ‘60s feel. To complete the look: a pair of chunky black boots, another go-to, from Camper. And that was it! Looking to recreate this fit? Here’s where to shop every item (minus some sold-out or unavailable items, which I’ve replaced with worthy alternatives).