Pamela Anderson’s Leopard Pillbox Hat Is the Unexpected Accessory of the Season

“Pamela Anderson leopard hat” was not a phrase I expected to type (with vigour) into my Google search bar this morning, but, when you think about it, it makes sense. Here’s a woman with a storied history when it comes to hats. There was, of course, the gargantuan, fluffy bubblegum-pink style (very Emma Brewin, actually), which Anderson iconically parodied with Jacquemus. Then, there was—yet another ginormous—wide-brimmed, braided top-hat-esque creation. There has been a whole host of cowboy and baseball caps, now added to her sartorial canon is a leopard-print pillbox hat, reminiscent of Jackie Kennedy — another woman with a penchant (and the face) for a hat.

The mid-century staple might seem an unlikely choice for Anderson, whose affection for wide-brims is well-documented, but her recent styling has leaned into a distinct vintage vibe. She’s been spotted carrying Strathberry’s sculpted Mosaic bag, paired with Grace Kelly curls and a jewel-toned twinset. Other vintage nods: cat-eye sunglasses (an array), a pussy-bow blouse, and a flowing lemon maxi skirt with a matching Ralph Lauren cable-knit sweater—very Connecticut, very Kennedy.

The hat, however, was the crowning (literally) touch. Styled with a black wool faille cape dress that cinches at the waist with a leather ‘Hug’ belt, and matte black leather ‘F-buckle’ pumps—both from Ferragamo—the look was completed with face-framing curls and elegant gold huggie earrings.

Anderson isn’t mounting a one-woman attempt to relaunch the once-staple hat, either. Pillbox hats made a notable appearance on the Spring/Summer 2025 runways of Chloé, Loro Piana, and Valentino, while Maria McManus went a few decades earlier, reimagining the 1920s cloche hat in sugar-white with cheek-grazing straps.

Fashion consultant and content creator Leila Kashanipour has also been championing vintage headwear, showcasing a dizzying array of turbans and pillbox hats to her 140k+ following. Perhaps the pillbox will go the way of the capri pants before it — there once was a time a woman wouldn’t dare dream of leaving the house without a hat (or so my nan used to tell me), maybe we’re headed that way again. Fashion is nothing if not cyclical.

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