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Jackie Apostel takes royal style cues from Princess Diana and Princess Kate in trending pillbox hat


The vintage silhouette hats are trending, and Cruz Beckham's girlfriend is leading the charge


Jackie Apostel wears a fluffy coat for a selfie © @jackie.apostel
Orion Scott
Orion ScottStyle Editor
2 minutes ago
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Move over knitted hoods and triangle scarves, there’s a new trending accessory for the winter season, and it pays homage to the swinging 60s in all its glory. 

Enter the pillbox hat. 

Leading the It-girl charge and championing the accessory for the cosy season ahead is Brazilian-German musician and girlfriend of Cruz Beckham, Jackie Apostel

Jackie Apostel poses in a fur fringe coat and pillbox hat © @jackie.apostel
Jackie's elegant ensemble is a nod to 60s style in all its glory

Posting to her Instagram feed, Jackie shared a sleek, chic stylistic snap of herself with the caption ‘december ref’, the 29-year-old can be seen posing in a dreamy cheetah print fur trimmed coat from Charlotte Simone and a black pillbox hat, worn slightly tilted on top of a slick back bun. 

A screenshot of multiple pictures of Audrey Hepburn wearing pillbox hats © @jackie.apostel
Audrey Hepburn will forever be a style muse for the fashion obsessed

The next image in the carousel clearly proves Jackie’s inspiration behind the look, a screenshot of multiple Audrey Hepburn images from her prime in a variation of pillbox hats. 

What is a pillbox hat?

First popularised by Jackie Kennedy, the pillbox hat is a work of millinery art, named for its resemblance to old cylindrical pill containers. Consisting of a small, brimless hat with a flat top, usually in either a round or oval shape and featuring straight upright sides, the pillbox is a delicate occasionwear statement.

Diana, Princess of Wales, wearing a blue pillbox hat designed by milliner Gina Foster, smiles as she attends a reception at Swy-A-Lane Park on May 1, 1986 in Nanaimo, Canada© Getty Images
The Princess of Wales' iconic bright blue pillbox hat was designed by milliner Gina Foster

The stylish headwear option has been a constant go-to in royal wardrobes for decades, championed on repeat by Diana, Princess of Wales, throughout the late 80s and early 90s.

The Princess of Wales attends the annual Commonwealth Day Service of Celebration at Westminster Abbey on March 10, 2025 in London, England© Getty Images
The Princess of Wales isn't afraid of a pop of colour, just like her late mother-in-law

Fast forward to the 21st century, the Princess of Wales has been spotted taking style cues from her late mother-in-law on multiple occasions, styling a variety of pillbox colourways to match her on-duty outfits. 

Bella Emar wears black Meshki Blazer & pants© Getty Images
The statement style is flooding the street-style scene at the minute, worn by It-Girls around the globe

For AW25, the structured headwear statement is back in a big way, with cult favourite brands like Queens of Archive fuelling the trend with a new collaboration with fashion stylist, Rachel Bakewell. The new collection, which launched earlier this week online, features pillbox-style hats made in luxurious faux fur. Coined the ‘hot hat to have this season’ Rachel was inspired by: “The iconic shapes of the 1960s - pillbox, cloche, and toque - have long fascinated me, and I aimed to reinterpret these vintage silhouettes with a modern twist.”

If you’re in the market for an elegant answer to cosy dressing this festive season, a pillbox hat is set to be the next big thing in cold-weather dressing. 

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