Pillbox Hats Are the Unexpected Accessory We're Using To Elevate Every Autumn Outfit

A hat trend coming into its own now that the weather has turned colder hardly feels revolutionary. Beanies and bobble hats come part and parcel with the change of seasons as we all brace ourselves against the impending cold weather. This year, however, it’s not practicality that’s driving our latest hat obsession. Instead, this is a trend that lives solely for sartorial joy. First spotted both on and off the catwalk at Copenhagen Fashion Week and Oslo Runway earlier this year, and now gaining momentum here in the UK too, the pillbox hat is officially winter 2025’s ultimate accessory.

I say first spotted earlier this year; however, of course, the pillbox hat’s history stretches back much further. Originally a military style, it went through a transformation in the 1930s, shedding its service roots and taking on the sleek, stylish interpretation we know today. It wasn’t until the 1960s, however, that the pillbox hat truly came into its own. Worn by US First Lady Jackie Kennedy, the cylindrical style became synonymous with femininity and elegance, and so, unsurprisingly, it’s still favoured by aristocracy and royals, including Kate Middleton, today.

This winter, however, the pillbox hat is going through another transformation. Yes, it’s still polished, offering an air of understated elegance; however, now the cool girls have adopted it as their accessory of choice. Worn alongside their favourite winter coats, sleek suiting and even their best autumn dresses, this year, the pillbox hat feels effortless, interesting and wholly unexpected all at the same time.

While among street stylers and influencers, its classic black and off white iterations that are proving most popular — mirroring the pillbox hat’s understated design and leaning into our longstanding love for minimalist styling — they aren’t the only ways to wear the trend. On the catwalk at AKS, faux fur pillbox hats were styled with coordinating faux fur coats while Pamela Anderson stepped out in a leopard print style, tapping into the animal print trend, earlier this year.

It’s clear, however you choose to put your spin on it, the pillbox hat is making moves this season, so what better time to get your hands (or your head) on one…

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