Jackie Kennedy Onassis loved them, Bob Dylan sang about them – and pillbox hats were a popular accessory in the ’50s and ’60s that are making a comeback.
“The ‘pillbox’ is a traditional shape that was popular in the 1950s,” says New York City milliner Gigi Burris. Her namesake brand is available in four different popular pill box styles. “It’s round in shape with straight sides. Ladylike dress is on the rise, with gloves, brooches and hats added.” Burris said the business’s popularity has recently increased by 50 percent.
Vogue archivist Laird Borrelli-Persson witnessed the resurgence from a front-row seat while covering Copenhagen Fashion Week. “There was an undercurrent of early 1960s style,” she said. “The pillbox itself will always be associated with Jackie O, who wore it during a time of great hope and later became a figure of national tragedy.”
Rachel Tashjian, razor-shaving senior reporter CNNKnown for wearing many hats, in addition to Jackie O., she also found inspiration in Rembrandt paintings, Renaissance portraits, and different styles of headdresses worn by religious figures. “The sheer volume and drama of the books was very illuminating,” she told me. “Pillbox hats look cute, so I like to play with maximalism.” If you want to go bigger, Tashjian recommends looking for pieces by Romeo Gigli and Yohji Yamamoto.
During the chilly but always whimsical CPFW, we saw a dozen tops that proved you don’t have to wear a full skirt suit and flip out a blowout coat. Instead, pillbox hats—which came in shades of black, red, and white, as well as plenty of leopard print—were styled with double Dutch braids, buns, and natural hair.
“Maybe [there is] Borrelli-Persson said of the return of Pill Box Hat, “It’s a subconscious yearning for an era of youth and hope in America.” “It was the moment when the youngest man ever entered the White House, and his stylish wife carefully redecorated the White House, which she had won in her youth. Fashion Essay contest! “

