Jackie O didn’t invent the pillbox hat.  She just made it iconic.  Few realize that she started wearing the hat on the back of her head to minimize the “flat hair” that you sometimes get from wearing hat.  Ironic isn’t it then? This simple gesture became her signature style and turned pillbox hats into an icon of modern elegance.

In the book “Jacqueline Kennedy: The White House Years,” Hamish Bowles remarked that Jacqueline revolutionized the taste of the nation. As first lady, she put “style” into the White House both literally and figuratively.  She redecorated the place and made state receptions into “events.”  While her preferred couturiers were French: Chanel, Balenciaga and Givenchy, she understood the importance of showcasing American designers.  This was not an easy task since the fashion world at that time, only considered the French as having anything worth saying.  In a stroke of brilliant timing, American designer Oleg Cassini wrote to Jackie asking to work with her on some dresses. He was able to create fashion statements of extreme elegance without experimentation which was just want she wanted.

In the late 1950s, part of every well-dressed wardrobe included a range of hats.  In 1959, French designers were showing pillbox hats in their collections. While Jackie-O didn’t particularly like hats she found that small pillbox hats worked well with her voluminous hair. She turned to a place where many New York women have turned.  Bergdorf Goodman, on the corner of 5th Avenue and 57th Street.  There she worked with Halston and ordered several domed pillbox hats for key outfits.  She tilted her hat back and the rest is history.

Since vintage pillbox hats are back in fashion, I thought it worthwhile to offer some advice on how wear and secure a pillbox hat to your hair.  First you need to know what size to purchase.  A classic Jackie-O vintage pillbox hat, tilted back on the head is generally about an inch smaller than your head size.  You can use an elastic, which goes under your hair to hold the pillbox in place when it sits straight.  The elastic should be close in shade to your hair color.  However, if your pillbox hat sits back, I’ve found that 2 combs on the side of the hat work best to hold it in place.  If you want some EXTRA staying power use bobby pins through the combs to provide the staying power of super glue.

Now I have a question for you.  What’s the best place to find vintage pillbox hats?  Share this with your comments to help other pillbox hat lovers.