Leopard Pillbox Hat Emerges as Unexpected Fashion Statement of the Season, Courtesy of Pamela Anderson
In the world of fashion, trends often come full circle, and the latest revival is the iconic 1960s pillbox hat. Popularised by figures such as Jackie Kennedy, the pillbox hat has made a notable comeback, thanks in part to Pamela Anderson's recent vintage-inspired leopard-print pillbox hat.
Anderson's appearance in London promoting her new film, The Naked Gun, showcased this revival, with the pillbox hat paired with a belted cape dress from Ferragamo’s fall 2025 collection. This fusion of vintage glamour and contemporary chic was a clear nod to the mid-century elegance that the pillbox hat embodies.
The pillbox hat, originally military headgear turned fashion staple, has also been spotted on the Spring/Summer 2025 runways of Chloé, Loro Piana, and Valentino. This resurgence signifies a broader revival in hat-wearing culture, with fashion influencers and consultants like Leila Kashanipour advocating for vintage headwear.
Kashanipour, who has 140k+ followers on social media, has been showcasing turbans and pillbox hats to her audience, fostering wider adoption of the style beyond celebrity circles. However, her advocacy does not include the large pink bubblegum-style hat or the large braided top-hat-esque creation.
The pillbox hat's appeal lies in its versatility and ability to channel Old Hollywood glamour while remaining fresh and playful. The leopard print adds an unexpected modern edge, playing into the cyclical nature of fashion where vintage styles are being reimagined with new patterns and styling.
This trend's influence is both cultural and stylistic. It underscores a renewed interest in headwear as a statement accessory, potentially encouraging more women to embrace hats as a daily fashion element, similar to past decades. The look channels Old Hollywood glamour while remaining fresh and playful due to animal print and contemporary tailoring, showing vintage pieces can be reinvented for today’s aesthetic without strict historical mimicry.
Fashion influencers and consultants are supporting the pillbox hat’s comeback, fostering wider adoption beyond celebrity circles. Designer Maria McManus has reimagined the 1920s cloche hat in sugar-white with cheek-grazing straps, further demonstrating the versatility of vintage headwear.
As Anderson continues to champion this vintage-inspired style, it seems the pillbox hat might become as ubiquitous as capri pants were in the past. Whether you're a fan of the original or prefer the modern twist, there's no denying that the pillbox hat is making a significant impact on the fashion scene.
The renewed interest in the pillbox hat, as showcased by Pamela Anderson, signifies a shift towards vintage headwear in the fashion industry. This style, originally popularized by Jackie Kennedy, is now being embraced by fashion influencers and consultants like Leila Kashanipour and designer Maria McManus. The versatility of the pillbox hat allows for modern reinventions, as seen in Anderson's leopard-print version, and McManus' reimagined 1920s cloche hat. This trend suggests a possible return of hat-wearing as a daily fashion element, similar to past decades, and underscores the cyclical nature of fashion where vintage styles are being reimagined for a contemporary aesthetic.
