Isabella Blow, often regarded as one of the most stylish people who ever lived, was once described by legendary fashion critic Cathy Horan as “the woman that no hat could tame”. With a preference for eccentric millinery, she was often spotted in the front rows at shows for Dior or her former protégé Alexander McQueen, wearing surrealist and sculptural headpieces: a lobster hat decorated with pink Swarovski crystals, air light feathers that spelt out her last name, an 18th-century-inspired ship. Today, our penchant for hats is far less daring than hers, but it’s a potent reminder of the power that this understated accessory holds.
That’s not to say that we as a society have completely forgotten about styling our outfits from top to bottom, right up to the cap or cloche that finishes off our ensembles. The past few seasons have made great headway in reintroducing, well, headwear back into our wardrobes. From the rise of Grace Kelly-esque silk scarves to the bandanas Gracie Abrams helped reprise during her debut Glastonbury set, those with taste aren’t averse to donning a hat that makes a statement.
These days, however, styling a chic hat isn’t as simple as throwing on a backwards cap and thinking your work is through. As the key hat trends are proving, this style is becoming less of an afterthought and more integrated into the overall look, making investing in one a considered choice.
You could go the route of one of Truman Capote’s “Swans” and wear a pillbox hat like you’re some Upper East Side socialite heading to lunch at La Côte Basque. Or, make like Keira Knightley in Love Actually and pair your baker boy hat with an oversized military jacket. Though if you do the latter, make sure you remind whoever comments on it that you’re wearing it in a Khaite autumn/winter 2025 way, and not an ironic Y2K way.
Whatever you decide, it’s apparent that hats need not be relegated to the back of your wardrobe any longer. Stylish, sophisticated and spotted on the heads of every cool dresser, scroll through for the key hat trends to know.
5 Key Hat Styles Trending in 2026
1. Raffia Wide-Brim Hat
Style Notes: Wide-brim sun hats bring an added dimension to the breezy and wafty ensembles we wear during warm weather moments. When rendered in a raffia fabrication, they nod to the perennial legacy of summer wardrobe staple, the basket bag. Plus, there’s something Victorian-woman-going-to-the-seaside-to-get-well that feels indisputably subversive and polished. (Ideal for anyone whose favourite character in The Little Woman has always been Beth.)
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2. Pill Box Hat
Style Notes: Jackie Kennedy might’ve had her iconic dusty pink Halston pillbox hat, but nowadays, there are plenty of covetable options that would’ve rivalled hers. From tassel scarves to opera jackets, this style is another staple in the “ladies who lunch” repertoire, offering a sculptural yet glamorous sensibility to any silhouette. Best accompanied by soft tailored pieces like an elongated trench coat and slouchy long shorts, opt for iterations rendered in leopard print or trimmed with shearling for a more modern touch.
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3. Crochet Skull Cap
Style Notes: As the latest designer collections indicate, we’re currently in the throes of the roaring 2020s. From two-toned shoes to prohibition embellishments, fashion is firmly in its Bugsy Malone era. This Jazz Age redux is trickling through to the leading hat trends, with the gilded headpieces worn by flappers during the decade—and yes, Sabrina Carpenter in a custom Dior version at the 2026 Met Gala—making a triumphant comeback a century later. This time around, however, they’re less chintzy and more relaxed, taking after the woven crochet pieces you’ll spot on every beach from Mallorca. Approved by the most stylish denizens in both Denmark and the Balearic Islands, this style oscillated between shipwrecked chic and Gatsby opulence with ease.
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4. Knitted Bucket Hat
Style Notes: The frazzled English woman was in desperate need of a rebrand, and thankfully, the knitted bucket hat was here to deliver one. Because who wants to identify with the hapless-in-love Kate Winslet in The Holiday when you can dress far more sophisticatedly like Cameron Diaz’s character? Whilst still possessing the same charming and bumbling qualities of our favourite rom-com leads, you’ll now find knitted bucket hats more associated with the likes of Kendall Jenner and Jennifer Lawrence than Bridget Jones, especially when paired with elegant long coats and a bag from The Row. (Sorry, Bridge, but there is no way your TV reporter salary is covering the cost of a Marlo.)
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5. Newsboy Hat
Style Notes: However, if feeling like you’re in a rom-com is what you’re after, the newsboy hat might also provide a solution. As previously mentioned, it first rose to prominence in Richard Curtis’s iconic Christmas film when spotted in that scene with Keira Knightley, but quickly fell into obsolescence soon after. Now, with co-signs from Prada and adherents of JFK Jr’s ‘90s wardrobe, this style has become ubiquitous, despite its controversial status. A style to herald in, indeed.
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