This "Dated" Hat Style Is Back, and Is the Answer to Elevating Your Winter Outfits

As someone who possesses an eagle eye for emerging trends and likes to think of herself as an early adopter, when I started seeing fashion's most elite dressers wearing this accessory, I knew I needed in. From Scandi girls in Oslo and Copenhagen to the streets of the Upper East Side in New York and now East London, too, the pillbox hat is fast-becoming the item du jour. You'd be forgiven for thinking this style is quite old-fashioned, but having recently bought into the trend myself, I can attest to how wearable and easy to style it actually is.

Pillbox hats became popular during the 1930s, thanks in part to American First Lady Jacqueline Kennedy, who is considered a fashion icon and the epitome of elegance and good taste. Now, people with a discerning eye are looking back and taking note, and with a renewed penchant for dressing up, vintage-leaning style and all things eye-catching, the pillbox hat is finding a fresh value in 2026.

Now, admittedly, this isn't the type of accessory you can throw onto a sweats, leggings or athleisure look. Women today are pairing their pillbox hats with outfits that possess a wealth-whispering, grown-up and elevated appeal, and it's a look that is surprisingly easy to master. Wool coats, shearling and faux-fur jackets and suede trenches are the outerwear options that team well here, plus pencil skirts, tailored trousers, high-denier tights, court shoes, loafers or even heeled leather boots. In short, items that feel pulled-together, polished and graceful—worthy of the wardrobe of a First Lady.

Having come into possession of a leopard-print pillbox hat recently, which I found in my local charity shop, I've found myself reaching for it a lot more than expected, as it finishes my everyday looks with a considered and chic punctuation mark. It has turned heads on the Tube, but I don't mind the attention it garners; I've been leaning into the Mrs Robinson energy it brings! As such, I'm keen to find a few more pillbox styles to add to my Monday-to-Sunday repertoire.

If you, too, are eager to step back in time and get the look for yourself, I've sourced some of the best pillbox hats available to shop now, in a chic array of colours, shapes and styles. Scroll on for my edit.

Shop the Pillbox-Hat Trend: