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Vintage Pillbox Hats and the Women Who Made Them Fashionable

I have been blogging and writing online since 1996. I enjoy topics as varied as graceful aging, self-care, and vintage hats.

Post-War Fashion History

In 1950, America was just getting used to post-war prosperity. The war was won and the boys were home, and America's factories were churning out cars and washing machines instead of guns and airplanes. Rosie the Riveter was back home baking cookies and having babies. There was a longing for peace, stability, and family, and this was reflected in contemporary fashions.

Dior had unfurled his "New Look" in Paris a few years before in 1947. This was a lush, feminine fashion statement of long skirts, high heels, and wasp waists that took post-war Europe and America by storm. Its wide-brimmed picture hats, long full skirts, and stiletto heels lasted until January of 1961, when a young, fashionable first lady in the White House imposed her own fashion signature on America and the whole world.

Enter the Pillbox Hat

1961 was the year of the pillbox hat, and Jackie Kennedy was the woman who made it famous. She was wearing a pillbox on the cold January day her husband took the presidential oath of office, and she was wearing one in Dallas on the day he was assassinated. The pillbox was her signature, and through her, it became the iconic fashion accessory of the sixties and beyond.

Celebrities and movie stars like Audrey Hepburn followed the Kennedy lead. Hepburn was a big fan of the pillbox. Below is a shot of her from the film Charade, but she sported the pillbox look often—not just in films, but in her personal life as well. Her pillbox look was jaunty and sometimes included a veil.

Hollywood followed the Kennedy lead. Here's Audrey Hepburn in a pillbox hat in the film "Charade."

Hollywood followed the Kennedy lead. Here's Audrey Hepburn in a pillbox hat in the film "Charade."

The Return of the Pillbox With Millennials

In general, hats went out of style somewhere around 1970 when fashion did an about-face. Between London's "Mod" look (think Mary Quant and the Beatles) and the Woodstock generation (think calico dresses, combat boots, and peace symbols) hats were a definite no-no for both men and women.

The young and forward-thinking went bareheaded. Hats were considered "old hat," and only conservative old men and frumpy grannies wore them. Old men tipped their hats to old ladies who were not only wearing hats, but also gloves. In fact, hats and gloves became the mark of the old and stodgy and so it was for the next three decades until the Millennials, aka Generation Y, decided that hats were hip and proceeded to make them their signature.

Vintage Fashion Comes Back in Style

The kids started combing vintage clothing stores and avant-garde designers started creating—yes, folks—hats! Young fashionistas have brought new life to the old pillbox, pairing it with everything from junky jeans to retro formal attire and creating a whole new fashion-forward look for it. Madonna and the Kardashians as well as the kids on the corner have embraced the Pillbox and made it their own. Hats are back and they are not your grandmother's pillbox—or maybe they are!

Today, hats are everywhere—there are even blogs about hats, online shops that deal in nothing but hats, and high-end milliners who are making a comeback designing for such luminaries as Paris Hilton and Lady Gaga. These are only two of the many contemporary celebs who are helping to resuscitate the pillbox hat after 40 years in the shadows.

How to Find a Pillbox

Where can you find an authentic vintage pillbox to top off your retro look? Try vintage clothing stores, flea markets, and yard sales. Much is available online. Check out eBay, and also try nosing around websites that specialize in vintage clothing and accessories. I'm a big fan of Etsy for this kind of thing, but there are a number of excellent sites that specialize in vintage hats and accessories.

Try googling "vintage pillbox hat" and see what comes up. You will be surprised at the number of choices. Of course, you can always buy a newly crafted, retro look hat from a number of designers, but that will probably cost you more and, for my money, is not nearly as much fun as finding and wearing a truly vintage piece.

I'd also suggest having a look in your mother's attic—chances are there is a pillbox hat up there somewhere. A great classic never goes out of style—and the pillbox hat is just that.

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© 2011 Roberta Kyle


Roberta Kyle (author) from Central New Jersey on December 11, 2016:

HI Angie, and thanks for your comment. I love vintage too, only for me it is a trip down memory lane. I love that you are re-discovering the pillbox hat. They really are a wonderful look. Enjoy !!!! and Merry Christmas to you and yours.

Angela Bodine on December 11, 2016:

Hi thank u so very much on your article. I was watching a documentary on Jackie Kennedy Onasis over a month ago.. They showed her with the pill box hat. I thought how cute, then I found vintage pill box hats on Etsy ..My kids got me one from the 1960s, for my bday a brownish peach bloom velour. CHRISTMAS THIS YEAR is about hats. I have a Tanish 1940s pill box, 1950s black pill box peach bloom velour, Cranberry peach bloom velour 60s pill box. .All vintage, but can't wear them till Christmas lol.. I also found vintage hat pins with pearl top to put on them..I love history so finding vintage pillbox hats and anything else vintage they all have a story wish I knew the stories on the previous wearer, or owner of furniture but now will have a newer story with me ..I wear handmade wool kilts 90% of the time and the pill box hats look cute with them. How is wearing my hair looks cute too. I even have Tams to match some of my tartan kilts...Thank you for this article. .Angie

Roberta Kyle (author) from Central New Jersey on March 01, 2012:

Thank you so much sandra, glad you liked the hub

Sandra Busby from Tuscaloosa, Alabama, USA on March 01, 2012:

I loved your article and photos. I voted up and beautiful Thanks. Sandra Busby

Roberta Kyle (author) from Central New Jersey on February 23, 2012:

Yup there is something iconic about the pillbox. I can't wear it either-- pillbox hats make me look like a pinhead. I need hats with big floppy brims for the shape of my face and because I am tall. But the pillbox is a great look isn't it? Thanks for stopping by Alecia

Alecia Murphy from Wilmington, North Carolina on February 22, 2012:

I don't know if I'd attempt the look but it's definitely interesting. I always feel my head's too big to wear hats and I sweat in my hair a lot as well but something about the pillbox is definitely iconic. Cool hub!

Roberta Kyle (author) from Central New Jersey on December 06, 2011:

wow-- that's a great find!

Beve on December 05, 2011:

Just found my grand mothers pillbox hat,

it still looks in great condition.

Roberta Kyle (author) from Central New Jersey on October 25, 2011:

and I love everything about your comment, tracykarl99-- thanks soooooo much :-)

Tracy from San Francisco on October 24, 2011:

I love everything about this hub! Wonderful pictures and great, vintage hat-shopping ideas. Your writing is very informative and flows nicely. Great hub - loved it. And of course, I happen to adore Beck :)

Roberta Kyle (author) from Central New Jersey on October 23, 2011:

Jackie was quite something, wasn't she? Truth is, she made me wish I could wear the pillbox, but I never could. They just didn't look good on me -- I look better in broad brimmed hats, so I guess I also get the side benefit of being shaded from the sun:-)

Laura Deibel from Aurora, CO on October 22, 2011:

I got some great memories of Jackie Kennedy in your article.

Truth is, I am a practical person and if that hat offers no shade from intensive sun, I won't wear it.

Roberta Kyle (author) from Central New Jersey on September 15, 2011:

Good to see you kenneth-- yes, my grandmother always said " a lady always wears a hat and gloves" and was into those little hats with veils too..... you are quite a writer yerownself and I really enjoy your hubs. Thanks for stopping by.

Kenneth Avery from Hamilton, Alabama on September 15, 2011:

Dear robie2, excellent hub. You are an excellent writer and lay-out artist also. My grandmother on my dad's side wore a hat each time she went in public...even a veil on Sundays...she loved those small pillbox hats you talk about. Thank YOU for rekindling a fond memory.

Roberta Kyle (author) from Central New Jersey on July 31, 2011:

Thanks Pamela-- I always think of Jackie O when I think of the pillbox hat. Glad you enjoyed the hub. It was fun to write.

Pamela Oglesby from Sunny Florida on July 30, 2011:

Excellent hub and it brings back memories of my mom wearing those hats. The pill hat really is so attractive. Rated up and beautiful.

Roberta Kyle (author) from Central New Jersey on March 04, 2011:

thanks SAlly-- good to see you as always. I loved " The Nanny" the first time around too.

Sherri from Southeastern Pennsylvania on March 02, 2011:

We can also take a look at our TV attics to see pill box hats at their finest, and I'm talking about The Nanny sitcom with Fran Drescher currently on cable TV reruns.

This lady/character had style!

She could get a pill box on her huge hair and wear it perfectly.

Wonderful retrospect, Robie.

Roberta Kyle (author) from Central New Jersey on February 10, 2011:

yenajeeon--how does the pillbox stay on? depends on the size of your head and how far back you wear it on the head, but yes, hatpins can be a good help-- hmmmm wonder if now that hats are making a comeback, if hatpins will do the same? thanks for stoppng by and commenting

Yena Williams from California on February 09, 2011:

These pillbox hats are to die for they're so cute! I really want a furry one made of mink perhaps. How do they stay on? With pins?

Roberta Kyle (author) from Central New Jersey on February 07, 2011:

Thanks KS-- I bet that pillbox would fetch a pretty penny on ebay or etsy these days.

KsCharles on February 07, 2011:

I enjoyed this revelation of love and respect for hats so much. How I wish I'd kept my beautiful pillbox, instead of selling it at a years-ago garage sale.

Roberta Kyle (author) from Central New Jersey on February 07, 2011:

totally agree, Princessa-- both vintage and timeless IMHO

Wendy Iturrizaga from France on February 07, 2011:

A beautiful accessory to wear to bring to life an otherwise simple dress!

Roberta Kyle (author) from Central New Jersey on February 06, 2011:

Me too Steph-- I wear big floppy sun hats in the summer but otherwise, am not much of a hat wearer either, but I love reading and writing about them:-)

Stephanie Marshall from Bend, Oregon on February 06, 2011:

I think hats are so interesting - love looking at photos and reading about them, though I'm not much of a "wearing hats" person. Great photos of Lady Gaga and Paris Hilton - pillbox hats really are timeless!

Frieda Babbley from Saint Louis, MO on February 06, 2011:

How cool. Great photos and info. Never heard the song in the video before (where have I been, right?), nice addition. Unfortunately, I'm not a pillbox gal, never could look good in one. But I love love love seeing them on people. Elle wears one in Legally Blonde. Cute cute cute! Great hub, Robie2.

Roberta Kyle (author) from Central New Jersey on February 06, 2011:

Thanks for the comment Alek-- I remember them too, but never wore them-- they didn't look good on me-- however I thought Jackie looked smashing!!!!

Nancy Hinchliff from Essex Junction, Vermont on February 06, 2011:

Fun hub. Those hats were so cute...I remember wearing them myself. Thanks for the trip down memory lane. :=)

Roberta Kyle (author) from Central New Jersey on February 06, 2011:

Hi UW and Amy. Thanks for reading and commenting. I don't look good in most hats-- only those really wide brimmed floppy things look good on me and I rarely wear them-- but I love the idea that the twenty something crowd is re-discovering the hat as a fashion accessory. Long live GenY!!

amy jane from Connecticut on February 06, 2011:

Love it! Pillbox hats are so cute. Like Uninvited Writer, I don't look great in hats. :( Maybe, maybe, these would work for me! :)

Susan Keeping from Kitchener, Ontario on February 06, 2011:

Great stuff. I don't look good in hats :)

Roberta Kyle (author) from Central New Jersey on February 06, 2011:

and thank you, twilight, for sharing your memories and for taking the time to read and comment.

Twilight Lawns from Norbury-sur-Mer, Surrey, England. U.K. on February 06, 2011:

Great memories. I remember seeing my mother wearing a red straw pillbox with a red veil in the early forties, and I have a couple of photographs of her wearing a large black straw coolie hat with a black taffeta Dior New Look dress. The effect was stunning. Thank for a lovely hub which brought back a lot of personal memories.

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