Vintage Pillbox Hats and the Women Who Made Them Fashionable

Updated on November 11, 2019
robie2 profile image

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

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Jackie Kennedy in her trademark pillbox hat.Jackie and JFK on Inauguration Day, 1960.
Jackie Kennedy in her trademark pillbox hat.
Jackie Kennedy in her trademark pillbox hat. | Source
Jackie and JFK on Inauguration Day, 1960.
Jackie and JFK on Inauguration Day, 1960. | Source

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." | Source

The Return of the Pillbox With the 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 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 forty years in the shadows.

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Gen Y's take on the classic pillbox.Princess Diana in a pillbox in 1989.Paris Hilton sports a retro pillbox, proving the pillbox is forever.
Gen Y's take on the classic pillbox.
Gen Y's take on the classic pillbox. | Source
Princess Diana in a pillbox in 1989.
Princess Diana in a pillbox in 1989. | Source
Paris Hilton sports a retro pillbox, proving the pillbox is forever.
Paris Hilton sports a retro pillbox, proving the pillbox is forever.

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.

Questions & Answers

    © 2011 Roberta Kyle


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      • robie2 profile imageAUTHOR

        Roberta Kyle 

        3 years ago from Central New Jersey

        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.

      • profile image

        Angela Bodine 

        3 years ago

        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

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        8 years ago from Central New Jersey

        Thank you so much sandra, glad you liked the hub

      • sandrabusby profile image

        Sandra Busby 

        8 years ago from Tuscaloosa, Alabama, USA

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

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        8 years ago from Central New Jersey

        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 profile image

        Alecia Murphy 

        8 years ago from Wilmington, North Carolina

        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!

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        8 years ago from Central New Jersey

        wow-- that's a great find!

      • profile image


        8 years ago

        Just found my grand mothers pillbox hat,

        it still looks in great condition.

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        8 years ago from Central New Jersey

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

      • tracykarl99 profile image


        8 years ago from San Francisco

        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 :)

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        8 years ago from Central New Jersey

        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 in Denver profile image

        Laura Deibel 

        8 years ago from Aurora, CO

        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.

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        8 years ago from Central New Jersey

        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 profile image

        Kenneth Avery 

        8 years ago from Hamilton, Alabama

        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.

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        8 years ago from Central New Jersey

        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.

      • Pamela99 profile image

        Pamela Oglesby 

        8 years ago from Sunny Florida

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

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        9 years ago from Central New Jersey

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

      • Sally's Trove profile image


        9 years ago from Southeastern Pennsylvania

        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.

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        9 years ago from Central New Jersey

        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

      • yenajeon profile image

        Yena Williams 

        9 years ago from California

        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?

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        9 years ago from Central New Jersey

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

      • profile image


        9 years ago

        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.

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        9 years ago from Central New Jersey

        totally agree, Princessa-- both vintage and timeless IMHO

      • Princessa profile image

        Wendy Iturrizaga 

        9 years ago from France

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

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        9 years ago from Central New Jersey

        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:-)

      • stephhicks68 profile image

        Stephanie Marshall 

        9 years ago from Bend, Oregon

        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 profile image

        Frieda Babbley 

        9 years ago from Saint Louis, MO

        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.

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        9 years ago from Central New Jersey

        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!!!!

      • alekhouse profile image

        Nancy Hinchliff 

        9 years ago from Essex Junction, Vermont

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

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        9 years ago from Central New Jersey

        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 profile image

        amy jane 

        9 years ago from Connecticut

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

      • Uninvited Writer profile image

        Susan Keeping 

        9 years ago from Kitchener, Ontario

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

      • robie2 profile imageAUTHOR

        Roberta Kyle 

        9 years ago from Central New Jersey

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

      • Twilight Lawns profile image

        Twilight Lawns 

        9 years ago from Norbury-sur-Mer, Surrey, England. U.K.

        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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