The Pillbox Revival: A Perfect Circle in a World Craving Order

A little hat with a big comeback. This winter, fashion flirts with nostalgia and structure.

The Row Resort 2023; Look 40

The pillbox hat is back—but not in the way we've seen an overindulgence of bows or “office-siren” specs, thrilling one moment and overdone the next. This time, it’s deliberate. It’s sculptural. It’s charged with the kind of meaning that transcends itself. 

The pillbox hat seemed to re-materialize out of nowhere this season, cropping up across the runways as if by some unspoken agreement. The Row—because of course it was them—set the tone during their Resort 2023 presentation. The collection featured retro flourishes by way of pillbox hats, muffs, and top coats, signaling a nod to midcentury style.

L to R: Alaïa SS24, Prada SS24, Altuzarra FW24, Loro Piana FW24

By SS24, hints began to surface: Alaïa’s sculpted headwear and Prada’s sleek, swim-style caps pointed to a quiet resurgence. Then, as FW24 arrived, the pillbox was suddenly everywhere. Often crafted from structured wool, the pillbox slides seamlessly into colder collections, proving itself startlingly relevant today. Altuzarra turned it into the centerpiece of their easy wardrobing looks. The Row refined their vision, championing a softer silhouette, while Totême stripped it back to its minimalist essence. This wasn’t a slow burn; it was an eruption. Even Loro Piana is on board.

But how did we get here? Let’s rewind:

Pillbox Past: A Polished Origin

The pillbox hat doesn’t drape or flop. It doesn’t invite a casual glance. Perched with purpose, the pillbox is unapologetic—a forceful punctuation mark. 

Its origins trace back to military uniforms, where 19th-century officers wore pillbox-style caps designed to project authority and precision. Built for clarity and discipline before its strict geometry eventually slipped into the hands of mid-century designers who recast it into a symbol of elegance—serious elegance.

Halston's pillboxes—a Jackie Kennedy favorite

Balenciaga, a master in architectural fashion, saw its potential first. For him, the hat was an extension of his obsession with clean lines and structure, complementing the exacting silhouettes he championed. Halston, meanwhile, approached the hat with the tact of a milliner who knew his audience. During his time at Bergdorf Goodman, he wrapped pillboxes in velvet and satin, layering texture over precision. It wasn’t playful, but it had a sense of confidence—a hat for women who understood their own presence.

Grace Kelly often wore pillboxes in the 1950s, showcasing them as both regal and approachable. Audrey Hepburn, styled by Hubert de Givenchy, wore variations in films like Breakfast at Tiffany’s. Queen Elizabeth II, a consistent arbiter of formal headwear, incorporated the pillbox into her early wardrobe as a modern alternative to traditional hats, underscoring its ability to bridge old-world tradition with contemporary minimalism.

Then Jackie arrived. The pillbox on her was nearly a diadem; a boundary that framed her face but revealed nothing. It didn’t soften her. It didn’t need to. And instead, it became shorthand for a coronet for America’s Camelot fantasy. A promise that the cracks beneath the surface, wherever they might be, would never show. You didn’t wonder what lay beneath—because you wouldn’t find out. 

Her mother had groomed Jackie and Lee for this life anyway, molding them into ornaments of charm and composure, poised to marry well and navigate the corridors of power with ease. They weren’t just polished—they were conditioned. The pillbox became a declaration of control in a world where women were tasked with holding entire illusions together, as if their poise alone could preserve the facade. Jackie’s pillbox didn’t bend. It didn’t hint. It stayed exactly where it was supposed to, as did she.

The Row Resort 2023, Look 26

So why now?

The pillbox’s return feels eerily timed, as though it has something to say. By now, the cracks in our world aren’t waiting to show. The neat veneers we once relied on have fractured, peeling back to reveal what we’ve spent decades pretending wasn’t there. And yet here it is: the perfect circle. It offers no answers, no solutions. But maybe it doesn't need to. 

Maybe that’s the appeal, that the pillbox today doesn’t promise control. Maybe it’s an acknowledgment of the game, a way of saying we see the chaos and still choose the illusion. A final, deliberate grasp at sanity. Think: Gwyneth Paltrow’s Marge Sherwood in her leopard pillbox ensemble as she spirals into panic and unravels Tom Ripley’s masterplan. It’s not an admission of defeat, nor is it a bid for perfection. It’s a shape, a line, a circle, so sharply defined it dares you to question whether holding together is the same as holding on.

And somehow, there’s comfort in its structure, its defiance. The pillbox won’t soften for you. It doesn’t care about the mess unraveling beneath or around it. It's just there, unyielding, a reminder that sometimes style isn’t an escape. It’s an act of endurance.

As Bob Dylan sings in 1967...

You know, it balances on your head just like a mattress balances on a bottle of wine. Your brand new leopard-skin pill-box hat.

Altuzarra FW24; Look 9