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Vintage Pillbox Hats And the Women Who Made Them High Fashion

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Jackie Kennedy in her trademark pillbox hat
See all 7 photos
Jackie Kennedy in her trademark pillbox hat

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 stilleto heels lasted only until the beginning of the 1960's when a new young fashionable first lady in the White House imposed her own fashion signature on America and the whole world.

It was Jackie Kennedy who popularized the pillbox hat. She was wearing a Pillbox the 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 it became the iconic fashion accessory of the decade.

Jackie and Jack Kennedy on Inauguration Day 1960
Jackie and Jack Kennedy on Inauguration Day 1960

Audrey Hepburn in a Pillbox

Hollywood followed the Kennedy lead. Here's Audrey Hepburn in the film Charade
Hollywood followed the Kennedy lead. Here's Audrey Hepburn in the film Charade

The Return of the Pillbox

Movie stars like Audrey Hepburn followed the Kennedy lead. Hepburn was a big fan of the pillbox. Here's 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.

Hats in general 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 and combat boots and peace symbols) hats were a definite no no for both men and women. The young and forward thinking went bareheaded. The old , sedate, and conservative wore hats and so it was for the next three decades until GenY decided that hats were hip and fashionistas started combing vintage clothing stores and avant guard designers started creating-- yes folks-- HATS!

Today there are hats everywhere-- there are even blogs about hats, There are online shops that deal in nothing but hats, not to mention high end milliners who are making a comeback designing for such luminaries as Paris Hilton and Lady Gaga.

Gen Y Pillbox Adaptation

Gen Y's take on the classic pillbox
Gen Y's take on the classic pillbox
Source: Crafter.org

Lady Gaga in a Pillbox

Lady Gaga loves the pillbox look
Lady Gaga loves the pillbox look
Paris Hilton sports a retro Pillbox proving the Pillbox is forever.
Paris Hilton sports a retro Pillbox proving the Pillbox is forever.

Finding A Pillbox

Lady Gaga and Paris Hilton only two of the many contemporary celebs who are helping to bring back the pillbox from 40 years of obscurity.

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. Ebay an obvious place to look. 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 googlling " 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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Comments

Twilight Lawns 15 months ago

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.

robie2 15 months ago

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

Uninvited Writer 15 months ago

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

amy jane 15 months ago

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

robie2 15 months ago

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!!

alekhouse 15 months ago

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

robie2 15 months ago

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!!!!

Frieda Babbley 15 months ago

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.

stephhicks68 15 months ago

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!

robie2 15 months ago

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:-)

Princessa 15 months ago

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

robie2 15 months ago

totally agree, Princessa-- both vintage and timeless IMHO

KsCharles 15 months 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 15 months ago

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

yenajeon 15 months ago

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 15 months ago

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

Sally's Trove 14 months ago

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 14 months ago

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

Pamela99 9 months ago

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 9 months ago

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.

kenneth avery 8 months ago

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 8 months ago

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.

Laura in Denver 6 months ago

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 6 months ago

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:-)

tracykarl99 6 months ago

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 6 months ago

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

Beve 5 months ago

Just found my grand mothers pillbox hat,

it still looks in great condition.

robie2 5 months ago

wow-- that's a great find!

Alecia Murphy 2 months ago

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 alot as well but something about the pillbox is definitely iconic. Cool hub!

robie2 2 months ago

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

sandrabusby 2 months ago

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

robie2 2 months ago

Thank you so much sandra, glad you liked the hub

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