Pamela Anderson Revives Jackie Kennedy’s Pillbox Hat
Trust Pamela Anderson to reinvent a beloved vintage accessory with a modern flair. Anderson, out in London today promoting her new film, The Naked Gun, made the case for the pillbox hat—a 1950s staple loved by style icons like Jackie Kennedy and Audrey Hepburn—done in a decidedly unexpected pattern: leopard.
Anderson, sporting her signature blonde hair in tight, face-framing curls, wore the animal print topper while arriving at the Corinthia Hotel. The pillbox hat, known for its flat, upright sides and lack of a brim, was a staple of the ’50s and ’60s—but, like many historic pieces of fashion, is making a comeback on the runway and among celebrities. Paired with a belted cape dress from Ferragamo’s fall 2025 collection, the actor exuded old world elegance with a distinctly modern appeal. Her dress featured a nipped-in waist paired with a modest open-back detail at the reverse. Black slingback shoes, also from Ferragamo, completed the look.
The pillbox hat, which began as a form of military headgear, was a mainstay of Kennedy’s First Lady style. She infamously wore a pale blue topper to her husband’s inauguration in 1961, pairing it with a mod coat dress. In the decades to come, the accessory would become a go-to for political figures and Royals, with everyone from Princess Diana to Kate Middleton championing the silhouette. The accessory even inspired the Bob Dylan song “Leopard-Skin Pill-Box Hat” from his album Blonde on Blonde, which we suppose would be an apt place for Anderson to find inspiration.
Hepburn, too, was a fan of the headpiece, and even wore a leopard version in her film Charade.
Pillbox-inspired shapes were all over the spring 2025 runways of labels like Chloé and Valentino, with both offering different interpretations of the classic. For the previous spring season, the topper made its way into the collections of top brands like Alaïa, The Row, and Altuzarra.
Anderson’s style transformation over the past few years has seen her embrace refreshed twists on timeless silhouettes—this month alone, she’s made the case for monochrome summer dressing with a pair of ladylike looks. So, it shouldn’t come as a surprise to witness the actor complete her latest outfit with such a decided nod to vintage fashion with a refreshingly modern twist.
