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.
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.
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.
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.
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.
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.













