Jackie-O and Audrey Hepburn made this style hat into an icon. Pillbox hats offer a delightful choice of headwear and can provide the finishing touch to an outfit. While in the 1960s, they were worn straight on the head, today they feel more modern perched at an angle.  Wearing them this way lends an impertinent touch that just feels right. There are so many to choose among.  From small pieces perched saucily, to more dramatic ones that sit on the back of the head.  From actual vintage pieces, to vintage-inspired modern ones.  A pillbox hat turns a simple dress into an outstanding outfit.

Pillbox hats grab attention in a classy, elegant way.  So of course, you want your pillbox hat to stay put when you’re out and about.  Basically, there are two ways of keeping your chapeau firmly in place.  One method uses an elastic to anchor the hat.  The elastic should be the color of your hair and slip discretely under the hair.  Vintage pillbox hats are more likely to have combs on an elastic.  You pull the combs out slightly, grab a piece of hair to anchor them and that should hold the hat in place.