Are We Dressing Like First Ladies Now? A Pillbox Hat Trend Explainer

Although the history of the pillbox hat goes back to Roman times when soldiers wore them as military headgear, this small, round hat gained its widespread popularity in the 1930s before it hit its peak in the 1950s and 1960s. With First Lady Jacqueline Kennedy wearing a cream pillbox hat to her husband’s inauguration at the White House and style icons of the time like Audrey Hepburn and Princess Diana of Wales embracing the look soon after, it was no surprise that this flat-topped hat became the ultimate symbol of understated elegance of that period. 

While Jacqueline Kennedy is the indisputable icon of the pillbox look, Wicked’s buzzy 2024 press tour placed Cynthia Erivo as a modern contender for the ambassador of this hat style. With mouth-dropping Thom Browne looks styled alongside her contemporary iterations of the pillbox hat, we all held space for the actor’s unexpected masterclass in headpieces and fascinators. 

Looking at the bigger picture, it's clear that pillbox hats have been begging for their comeback since the Spring/Summer 2025 runways—and even the Fall/Winter 2024 shows. Brands like Chloé and Valentino showcased a stylish display of flat-topped headpieces in multiple colorways and textures. Far from embodying the classic '60s elegance, these modern pillbox hats were paired with bold, maximalist looks, speaking to a new type of cool-girl. 

Pillbox Hats on the Runway

While pillbox hats stand out for their simplicity and elegance, this brimless accessory is more versatile than it seems. Depending on the shape and size of the hat, this circular style can be worn pinned to the hair or placed at different angles to achieve many distinct looks. Plus, these small hats have a slighly different character depending on their details, like if they're embellished with lace, veils, feathers, brooches, or any other desired adornments for a more striking look. Whether crafted in velvet, satin, wool, or silk, pillbox hats symbolized sophistication and timeless charm for decades.

Jacqueline Kennedy Onassis and Princess Diana Wearing Pillbox Hats

While houses like Loro Piana, Maria McManus, and Altuzarra offered a more minimalist take on the pillbox style, they also proved that this charming hat silhouette can be seamlessly incorporated into urban attire. Paired with pleated skirts and casual sandals, these modern iterations of the classic pillbox look have the potential to become one of the must-have accessories of 2025. 

From renowned headwear names like Gigi Burris and Esenshel to contemporary fashion labels like Toteme and Nana Jacqueline, keep scrolling to shop L’OFFICIEL's favorite pillbox hats (and some other headpieces that capture the same vibe).