Hats Are This Season’s Most Whimsical Accessory

The last time I wore a “fun” hat I was a tween. I bought a newsboy cap from Aldo to channel the Britney Spears stand-in who starred in Justin Timberlake’s “Cry Me a River” music video. Actually, that’s not entirely true. I never ventured outside my bedroom in that hat. I couldn’t. I felt absurd. It was then that I learned if you’re not comfortable in something you’re wearing—no matter how trendy or designer it may be—it won’t look right.

It’s easy to feel ridiculous in a hat. So easy that I tend to forgo the accessory altogether—save for ones that serve a purpose, like a wide-brimmed hat on the beach to please my derm or a baseball cap on errand runs to hide limp locks. But that’s changing. The Spring 2025 collections feature a range of wonderfully purposeless fashion hats—ones that are so delightful, they’re compelling me to give the often-unnecessary accessory another go.

On the Prada catwalk, fringed and futuristic visors were paired with peacoats and polos, lending the looks a quirky edge. At Louis Vuitton, ornate bucket hats gave ladylike dresses a playful vibe.

At Chloé and Loro Piana, pillbox hats balanced masculine pieces with a prim-and-proper feel. And at Patou, head scarves (which we’ll lump in with the rest of these chapeaux for the sake of this story) offered outfits a fresh-off-the-yacht look. The message was clear: Hats, which have been function-driven for some time, are purely a decoration once again.

Take, for example, the Substack set. Some of the platform’s top fashion writers, like Leandra Medine Cohen, Monica Ainley de la Villardière and Laura Reilly, have hopped on the pillbox-hat trend, sporting theirs with minimalist separates (probably inspired by The Row 2024). Kendrick Lamar, Justin Bieber and Billie Eilish have been spotted in baseball caps worn purposelessly backwards. And Succession’s Jeremy Strong sported a turquoise velvet bucket hat at the Golden Globes earlier this year.

So, why are people now eager to perch a funny little decoration on their heads? “The world of fashion is getting more fun, and people are ready to stick out,” says Talia Brown Thall, a Toronto-based celebrity stylist and personal shopper. “Some of my clients love hats. I have a country musician who always wears a baseball cap, and his collection is ever so fun—all different colours and patterns. A hat can help pull a look together.”

When worn right, a decorative hat is like confetti sprinkles, edible flowers or a raunchy cake topper on a buttercream layer cake—a welcome dose of indisputable appeal. It’s a conversation starter—an easy way to expose a hint of your character. Think Andy Sachs wearing a tweed Chanel pageboy cap in The Devil Wears Prada or Carrie Bradshaw in a “fabulous” tiny fascinator that her boyfriend, Berger, mocks in season six of Sex and the City.

When worn wrong, though, a hat is costume-y. It’s beret-wearing North American tourists taking selfies at Carette in Paris or a gaggle of girlfriends in wide-brimmed felt hats and unbrushed curls in front of an autumnal backdrop.

So the question is “How do you do a purposeless hat right?” It’s easy: Do like the greats (Andy! Carrie!) and choose one you’re drawn to, no matter how prim or quirky it may seem, and look to the runways for inspiration to keep the look current. Personally, I’m drawn to the pillbox hat. It sounds intimidating, but after I saw a lineup of them at Chloé, teamed with easy bohemian separates and chunky gold jewellery, they suddenly read as very wearable—and very me.

This season, it’s easy to feel fabulous in a hat.

This article first appeared in FASHION’s Summer 2025 issue. Find out more here.