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Pillbox Hat – The Must-Have Accessory of the Fall/Winter Season 

November 17, 2025
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The fall–winter season brings together comfort, elegance, and a special kind of creativity that comes alive only at this time of year. It’s the season fashion lovers adore – a time when playing with textures, building layered looks, and choosing the right accessories creates a refined and distinctive style.



And let’s be honest: beyond its practical purpose, this season is the perfect moment for hats. Trends shift every year – a few seasons ago the wide-brimmed “shlyapa” were everywhere, and 2023–24 can easily be called the era of the balaclava. But what’s defining the current season? The answer is simple: the comeback of the pillbox hat is impossible to miss.



The pillbox actually has a long history that begins in the military world. It entered fashion in the 1930s, but its real rise to fame came in the 1960s thanks to Jacqueline Kennedy. As First Lady of the United States, she turned the pillbox hat into a symbol of elegance and aristocratic style – a legacy we still see reflected today in the looks of the Princess of Wales, Kate Middleton.



This season, the pillbox hat is everywhere – on the streets, at work, at evening gatherings, across social media, and in the style of influencers. It pairs perfectly with the key trends of fall/winter: blazers, coats, dresses, and classic two-piece sets.


Just like clothing, accessories also lean toward neutral palettes this season. Pillbox hats most often appear in black, white, cream, brown, and grey. But there are also playful versions with prints and embellishments – especially the ever-popular leopard pattern.



The pillbox’s minimalist shape, aristocratic charm, and modern reinterpretations give any look an instant touch of elegance and personality. So if you’re still deciding what accessory should define your style this fall–winter, trust us – the pillbox hat is the season’s smartest choice.

Tags: AccessoryPillbox HatTrend
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