The Rediscovered Elegance of the Pillbox Hat With the Success of Love Story, a Vintage Accessory Makes a Comeback

A Revival by Ryan Murphy

This spring’s must-watch series, Love Story, streaming on Disney+, is breaking all the records. Across nine episodes, it revisits the tragic love story of Carolyn Bessette-Kennedy and John F. Kennedy Jr. While viewers know the outcome, they remain captivated by every word, as if fiction could bend reality. Behind this success is the well-oiled machine of Ryan Murphy, the hitmaker also known for American Horror Story. Initially, it was Carolyn Bessette’s minimalist wardrobe-often compared to The Row avant la lettre-that drew attention, but another silhouette proves equally striking: Jacqueline Kennedy Onassis, portrayed by Naomi Watts.

Her bold, impeccably tailored Chanel suits form an instantly recognizable look. Yet it is the small, brimless hat, worn like a punctuation mark, that commands attention today. The pillbox, carefully coordinated with each outfit, weaves through the episodes as a visual thread. From John F. Kennedy’s inauguration to his tragic assassination in Dallas, it stands as a symbol of restraint, control, and elegance.

A Century of Reinvention

The Rediscovered Elegance of the Pillbox Hat With the Success of Love Story, a Vintage Accessory Makes a Comeback | Image 610147
The Rediscovered Elegance of the Pillbox Hat With the Success of Love Story, a Vintage Accessory Makes a Comeback | Image 610148
The Rediscovered Elegance of the Pillbox Hat With the Success of Love Story, a Vintage Accessory Makes a Comeback | Image 610149

The term “pillbox” literally means “pill box,” named for its compact, cylindrical shape. Before it crowned the heads of fashionistas, the pillbox was a military accessory, part of the British army uniform in the 19th century. It joins a long line of military-inspired items that have entered civilian wardrobes-from the cap to camouflage prints to the parka. After serving on the battlefield, its mission shifted. By the 1920s, it found its place atop women’s heads, crafted in velvet or fur and sometimes adorned with a veil, either sheer or opaque depending on the occasion.

It became a must-have in the 1950s and 1960s, thanks to figures like Jackie Kennedy. Though it belonged to a somewhat bourgeois wardrobe-slightly prim-the winds of freedom in the 1970s pushed it aside. It gathered dust for decades before resurfacing on another woman of influence: Princess Diana. Worn at official ceremonies, often carefully coordinated, it fulfilled a strictly ceremonial function. Today, it has returned to everyday fashion.

A Fresh Take?

The pillbox’s comeback is no coincidence. It is part of a broader reevaluation of classic codes, long considered outdated. Gloves, brooches, sharply tailored suits: all are reappearing in modern silhouettes, stripped of their original rigidity.

Luxury houses like Loro Piana, Valentino, and Alaïa, along with more accessible labels such as COS or The Frankie Shop, are all reviving the pillbox. It appears sometimes pared-down, sometimes creatively altered-a brooch, for example. Some personalities appropriate it to subvert its codes. Pamela Anderson, for instance, opts for a leopard version, breaking the notion of a necessarily prim, coordinated accessory.

@affie_kacar Alaïa inspired hat outfit #fashiontiktok #alaia #pillboxhat #hat #1950s #parisianstyle #minimalstyle #therealreal #secondhandfashion beautiful jazz piano in Autumn, 7 minutes(871493) - ricca

Wearing a pillbox is about embodying a certain ideal of representation, controlling the image with the precision of Jackie O. Fashion houses understand this. At Alaïa, Pieter Mulier’s precise lines gave each silhouette a sculptural quality. At Loro Piana, the epitome of quiet luxury, the pillbox receives a subtle makeover, gaining height to frame the face and dominate the silhouette. Contemporary minimalism is therefore not about erasure; it is about visual discipline. By revisiting pieces like the pillbox, fashion doesn’t just look back-it digs into its archives to rebuild accessories that resonate today. From Jackie O. to Love Story, and now across social media, the pillbox is poised to become the must-have hat of 2026.