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American Focus > Blog > Lifestyle > How to Wear a Pillbox Hat, According to Street Style
Lifestyle

How to Wear a Pillbox Hat, According to Street Style

Last updated: February 8, 2026 8:55 am
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How to Wear a Pillbox Hat, According to Street Style
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The classic pillbox hat, a beloved accessory of the 1950s and 1960s, is experiencing a resurgence in popularity. Renowned milliner Gigi Burris notes that the pillbox shape, characterized by its round shape and straight sides, is making a comeback alongside a renewed interest in ladylike dressing. Burris’ eponymous brand offers four different pillbox-esque silhouettes, reflecting the current trend towards gloves, brooches, and hats. The business has seen a 50% increase in popularity recently, indicating a growing appreciation for this vintage style.

During Copenhagen Fashion Week, Vogue’s archivist Laird Borrelli-Persson observed an undercurrent of early 1960s fashion emerging, with the pillbox hat taking center stage. Associated with style icon Jackie Kennedy Onassis, the pillbox hat symbolizes a time of hope and later, national tragedy. This classic accessory is being embraced once again, capturing the essence of a bygone era.

Rachel Tashjian, a senior style reporter at CNN, draws inspiration from a variety of sources, including Rembrandt paintings and Renaissance-era portraits. She appreciates the volume and drama of pillbox hats, opting for maximalist styles to avoid a cutesy look. Tashjian recommends exploring options from designers like Romeo Gigli and Yohji Yamamoto for a bold statement.

At Copenhagen Fashion Week, numerous pillbox hats were spotted in shades of black, red, white, and leopard print, styled in diverse ways with hair braids, buns, and natural textures. This versatile accessory proves that it can be incorporated into modern looks without adhering to a strict vintage aesthetic.

Borrelli-Persson speculates that the resurgence of pillbox hats may stem from a subconscious yearning for a time of youth and hope in America. Reflecting on a period when the White House was inhabited by the youngest president and his stylish wife, who won a Vogue essay contest in her youth, the pillbox hat represents a nostalgic nod to a bygone era of optimism and elegance.

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In conclusion, the pillbox hat’s revival is a testament to its enduring appeal and timeless style. As fashion continues to evolve, this classic accessory remains a symbol of sophistication and grace, resonating with a new generation of style enthusiasts.

TAGGED:hatPillboxStreetStylewear
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