Hat Trick! How to Wear a Pillbox Hat, According to Street Style

Jackie Kennedy Onassis loved them, Bob Dylan sang about them—the popular ’50s and ’60s accessory, the pillbox hat, is making a comeback.

“The ‘pillbox’ is a traditional shape popularized in the 1950s,” says New York City-based milliner Gigi Burris. Her eponymous brand has four different popular pillbox-esque silhouettes for sale. “It has a round shape with straight sides. With ladylike dressing on the rise and the addition of gloves, brooches, and hats.” Burris says the business has seen a 50% increase in popularity as of late.

Vogue’s archivist Laird Borrelli-Persson had a front-row seat to the revival while covering Copenhagen Fashion Week. “There is an undercurrent of early 1960s style emerging,” she says. “The pillbox itself is always associated with Jackie O, who wore it at a time of great hope and later became a figure of national tragedy.”

Rachel Tashjian, the razor-bobbed senior style reporter at CNN, is known for wearing many hats—and in addition to Jackie O., she finds inspiration in Rembrandt paintings, Renaissance-era portraits, and the different styles of headpieces worn by religious figures. “The volume and drama are very instructive,” she tells me. “Pillbox hats can look cutesy, so I like to play with maximalism.” If you want to go big, Tashjian suggests looking for one from Romeo Gigli and Yohji Yamamoto.

There were more than a dozen of the toppers spotted during the chilly but always whimsical CPFW, proving that you don’t have to go full skirt-suit and flipped blowout to wear one. Instead, the pillbox hat—in shades of black, red, and white, along with a lot of leopard print—was styled with double Dutch braids, buns, and natural hair.

“Perhaps [there is] a subconscious yearning for a time of youth and hope in America,” Borrelli-Persson reflects on the pillbox hat comeback. “It was a moment when the youngest person ever elected to the White House, which was thoughtfully redecorated by his stylish wife, who in her youth won a Vogue essay contest!”