The pillbox hat has been around for a long time, and has been worn by everyone from organ grinder's monkeys to Canadian police. It gained new life, however, in 1961, when a fashion conspiracy too shape.
Jackie Kennedy wanted a style all her own as she took over the role of first lady. Oleg Cassini had been a friend of the Kennedy's for years, and he signed on for the monumental task of First Stylist, with one caveat: that he be the only one to supply her clothing. Jackie was concerned about this, as this meant that he not only had to create clothing for each event, but also coats, gloves, hats, handbags and shoes. Mr. Cassini assured her that he was up to the task, and a partnership was born.
How would one person do all this without losing his mind? First of all: outsource. Jackie's hats were all created by Marita, at Bergdorf Goodman's, which took the actual construction work away from Cassini's house. Next, the style. He decided that what Mrs Kennedy needed was a "non-hat:" a style that would set off the beautiful face of the president's wife, instead of focusing on the hat itself. A correctly styled hat should be an afterthought, he said. It is an accent, not a focal point, which is exactly what the pillbox style is. Add to it that the simplicity of the style meant that it could be made up by Bergdorf Goodman's without a national summit of what the hat would look like.
Look at what a properly worn pillbox hat looks like:
She looks radiant, does she not? Note that her face is the focus, and how the hat frames her face - almost like a halo. Perfect.
A couple of other well-done pillboxes:
Audrey Hepburn in "Charade," in 1963.
An almost pillbox, worn by Grace Kelly in Rear Window, 1954. The veil makes a nice accent, but is definitely more a focal point than a plain pillbox.
I doubt seriously that there is anyone who will look at a pillbox hat perched on the back of a woman's head and not be reminded of Jackie Kennedy, so the fashion conspiracy worked. Jackie took a simple style, made it all her own, and created fashion history in the meantime. And that is something that just doesn't happen every day.