Tracing the Checkered History of Hats on the Red Carpet

“Hats are radical,” milliner to the stars Philip Treacy once said. “Only people that wear hats understand that.” The British actor Florence Pugh can now count herself among their number, having swept into the London Critics’ Circle Film Awards wearing a deep red peplum gown from Robert Wun’s spring couture collectsion, complete with a matching wide-brimmed hat and trailing veil. Though Pugh is a playful dresser, this was a surprisingly bold choice for one of the more low-key dates on the awards season calendar. And while it’s not the Wun accessory we would have chosen for the star (that honor goes to the glass of red wine one model toted on the designer’s runway last month), it was perhaps appropriate for a night that was all about celebrating drama. 

With its swooping brim, Flo’s chapeau also recalled another memorable piece of headgear: the white asymmetrical hat Celine Dion wore to the Oscars back in 1999. A custom piece by Stephen Jones, Dion wore her cocked fedora with a white tuxedo by John Galliano for Dior and some bedazzled shades. A million miles from the princess gowns that defined red-carpet dressing in the late ’90s, the look landed the singer on worst-dressed lists after the ceremony, but has since – in the manner of a young millennial starlet unfairly maligned by the tabloid press – been reassessed. (“It was avant-garde at the time,” Celine herself has said.)

While directional tailoring is now a familiar sight during awards season, the hat still represents tricky style territory outside of weddings and royal church services (where, as Princess Beatrice knows only too well, things still have the potential to go awry). But there are always those rare, redoubtable celebrities willing to take the topper to the red carpet, whether they go the retro route—like Elle Fanning, who revived Dior’s mid-century silhouette, complete with macramé hat, at Cannes—or lean into its meme potential, like Pharrell in a vintage Vivienne Westwood number that instantly spawned a parody Twitter account. 

Vogue revisits some memorable outings for hats on the red carpet, below.