Now that you’ve mastered the beret, it’s time to move on to the second most wearable hat on the planet: the pillbox. A nice pillbox is really no scarier than a beret. It’s very classic in a true-to-vintage way, but it’s also got clean modern lines and not too many extraneous details.
Here is the first iconic sixties pillbox hat photo:
And this is the second:
The pillbox obviously goes well with a ladylike skirt suit, but it also plays well with a harder edged look, like a jean jacket with a leather pencil skirt. Wear it back on the head like Jackie and Audrey did or give it a nice side tilt. Keep your hair simple, and bobby pin the hat to your hair.
Now play the Bob Dylan tune in your head as you walk down the street.
“I see you got your brand new leopard-skin pill-box hat
Well, you must tell me, baby
How your head feels under somethin’ like that?”
I’d say it feels sexy and nicely retro.