Winters Past Vintage in Micanopy, Florida

Featuring the Best of 20th Century Fashion

How to Wear a Vintage Pillbox Hat

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:

Jackie in a pillbox hat

Jackie in a pillbox hat, looking chic as always

And this is the second:

audrey helburn in a pillbox

Audrey Hepburn in an amazing leopard skin chapeau

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.

how to wear a pillbox hat

A black  pillbox hat with a little black dress

how to wear a vintage pillbox hat

Vintage head to toe, topped with a pillbox

how to wear a vintage pillbox hat

Very modern outfit with (you guessed it) a  vintage pillbox hat

Author: Winters Past

I am a vintage clothing shop owner living and working in rural north Florida. I believe in adding a little vinegar and molasses to my greens, having my coffee outside whenever possible, and mixing something vintage into every room and every outfit.

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