Before influencers and fashion magazines dictated style, everyday people were the true trendsetters—and nowhere is that more charmingly evident than in vintage photos from the 1920s to the 1960s.

In this post, we’re taking a nostalgic stroll through decades of street style, focusing on one timeless accessory: the hat. Whether it was a cloche, fedora, or pillbox, hats weren’t just fashion statements—they were a part of daily life. These candid snapshots offer a delightful glimpse into how real people wore their hats with effortless flair.

PLUS..it’s Easter this weekend so time to break out those Easter Bonnets.

1950s / 1960s vintage photo of a woman looking to be wearing her best Easter Outfit including a large corsage and an Easter Hat. She is wearing a two piece suit.

Source: Etsy-LightSilverAndPaper

Disclosure: Some of the links on my blog from Etsy , eBay are Affiliate Links, meaning, at no additional cost to you, I will earn a commission if you click through and make a purchase.

Vintage Photos Of Everyday People Wearing Hats 1920s-1960s

Liz note: There will be a few more 1940s photos then other era’s only because I really love 40’s hats.

1960s photo of two women in their Sunday best, which means stylish 1960s hats and fantastic dresses and coats.

1960s vintage photo of two Black Women in their 'Sunday Best'. They are wearing 1960s hats and 1960s dresses and one lady has a houndstooth jacket. Very stylish!

Source: Etsy-LightSilverAndPaper

Hello Gloria! “Tudor City – New York Easter Sunday, April 9th 1950. Not the easiest to see, but our pretty Gloria in the photo is wearing a hat of daffodils (I think). What style!

1950s vintage photo from 1950 of a woman name Gloria in a two piece suit and fur wrap, a floral hat and open toe shoes in Tudor City, New York on Easter Sunday. Fantastic early 1950s fashion.

Source: Etsy-therescuedphoto

1950s photo of a stylish couple posing on the sidewalk. Our 1950s woman is sporting a fantastic platter hat, fur wrap over a black dress and a great purse.

1950s photo / 1950s fashion of a stylish couple posing on the sidewalk. Our 1950s woman is sporting a fantastic platter hat, fur wrap over a black dress and a great purse.

Source: Etsy-LightSilverAndPaper

The 1920s had a love affair with the Cloche hat, as you can see on this stylish 1920s lady.

1920s vintage photo of a woman in a 1920s dress and 1920s hat, a cloche hat.

Source: Etsy-therescuedphoto

1930s or 1940s photo of a couple posing behind a bush. Our handsome gentlemen is sporting the popular ‘Newsboy cap’.

Now can we talk about that bush? Why are they in front of it? Are they not wearing pants? Ha!

1930s or 1940s photo of a Black couple posing behind a bush. Our handsome gentlemen is sporting the popular 'Newsboy cap'.

Source: Etsy-therescuedphoto

“Shine at Long Island with, Dollie, Jay, Kay & Papa – June 16th, 1940” (back & front of the photo captions).

Excellent early 1940s fashions on our men and women, especially the hats (see the ladies in the back?!). Dollie at the front is actually wearing a turban which was very popular for women during this time. Papa is sporting an always popular hat style for men, the ‘Boater Hat’.

Further Reading: A Vintage Guide to 1940s Hair Accessories

Early 1940s vintage photo of a group of men and women in early 1940s fashion (1940) out in a garden during the summer wearing early 1940s dresses, suits and 1940s hats for women and men.

Source: Etsy-LightSilverAndPaper

1940s vintage photo of 3 smiling men in 1940s hats and 1940s coats, trench coats. One of them is even holding a cigar. So dapper!

Speaking of dapper, did you know that the 2025 Met Gala theme is “Superfine: Tailoring Black Style –Black Dandyism“? If you did not, now you know. I cannot wait to see what everyone wears!

1940s vintage photo of 3 smiling Black Men in 1940s hats and 1940s coats, trench coats. Fantastic 1940s men's fashion inspiration.

I previously shared this image in a past post about ‘Toronto’s Easter Parade‘. It features two stylish women from the 1920s wearing their own take on men’s tuxedos, complete with top hats as headwear. They’ve added a playful twist with matching white, cowboy-style boots and floral lapel pins. I’m not sure who these women are, but they’re clearly turning heads and capturing the attention of the crowd.

1920s vintage photo of two women at Toronto's Easter Parade wearing their own take on men’s tuxedos, complete with top hats as headwear. They’ve added a playful twist with matching white, cowboy-style boots and floral lapel pins.

Source: City of Toronto Archives

1930s photo booth image of a woman sporting the popular French beret.

1930s vintage photo of a woman in a photo booth wearing a beret which was a popular 1930s hat style for women. She is also wearing a short 1930s bob vintage hairstyle.

Source: Etsy-therescuedphoto

Is that you Frank Sinatra? It’s not but I think our fedora sporting man has a similar look. Don’t you agree?

1950s vintage photo of a man wearing a fedora posing in a room with patterned curtains. 1950s men's fashion.

Source: Etsy-iloveyoumorephotos

Hats on every head! 1920s photo of a group of men posing in a parkette together. Page boys, flat tops and a fedora are in the image.

1920s photo / 1920s fashions of a group of men posing in a parkette together. Page boys, flat tops and a fedora are in the image.

Source: eBay

Spring time is the perfect time to pose with a friends in your favorite Easter Hat (or just a regular one) in front of a pretty blooming tree. I love the cute tilt hat on the lady on the left.

1940s vintage photo of two young women wearing 1940s hats posing in front of blooming trees during Easter time. The one woman is wearing a corsage and they both have 1940s hairstyles.

Source: Etsy-LightSilverAndPaper

April 1963-A dapper looking man in a bowler hat and suit and tie poses beside a flowering shrub in front of a row of tudor style buildings.

1960s vintage photo from 1963 of a Dapper Stylish Man in a Suit, Tie, bowler Hat posing by a flowering Shrub

Source: Etsy-LightSilverAndPaper

Late 1930s, early 1940s photo of two friends smiling together with matching corsages and very fun and interesting hats on their heads.

Late 1930s, early 1940s photo of two friends smiling together with matching corsages and very fun hats. Fantastic vintage fashion inspiration.

Source: Etsy-therescuedphoto

A 1950s photo of a woman wearing the iconic top half of the ‘Dior New Look,’ complete with a wide-brimmed hat—a signature accessory that echoed the elegant curves of the rounded shoulders and voluminous skirts that defined the silhouette.

Further Reading: The Fashions of Christian Dior 1947-1957

1950s vintage photo of a 1950s woman wearing a Dior New Look outfit, this includes the 1950s hat and 1950s jacket which would of been paired with a full skirt. She is wearing floral earrings. Fantastic 1950s fashion and 1950s hat inspiration!

Source: Etsy-therescuedphoto

1930s image of a young woman in a lovely 1930s dress and pretty hat next to a cannon. She is also wearing glasses, and as a eyeglass wearing gal myself I love photos like this.

Further Reading: Vintage Photos of Women Who Wear Eyeglasses

1930s vintage photo of a young woman in a 1930s dress, 1930s hat posing beside a cannon. She is also wearing glasses. Fantastic 1930s fashion.

Source: eBay

A 1940s photo of two kids dressed in their Sunday best—complete with matching-style hats. They’re absolutely adorable! I love our young lady’s look, and our little gentleman, all smiles in his suit, is just too cute for words.

I’d love to name the hats they’re wearing, but truth be told—I’m not sure what they’re called. Do any of my readers know? Drop a comment below!

1940s vintage photo of two Black kids in their Sunday best posing together. Both are wearing hats. So cute!

Source: Etsy-therescuedphoto

Vacation hat vibes! Here’s a fun 1960s snapshot of a woman rocking a tall straw hat with a ribbon tied just so—posing (somewhat reluctantly) next to a cactus plant. I can practically hear her husband saying, “Doris, touch the cactus for the photo!” And judging by the look on her face, Doris was thrilled about that idea. Ha!

1960s vintage photo of an older woman posing with a cactus plant in a 1960s shift dress and a 1960s straw hat. Cute 1960s fashion.

Source: Etsy-iloveyoumorephotos

I’ll end this post with a photo of my mom’s mom—my grandmother (Betty aka Elizabeth)—dressed in a lovely 1950s outfit (very Dior New Look inspired), complete with a charming hat adorned with what appears to be a feather on top. It’s clearly a special occasion, as she’s also wearing a corsage brooch. I think her choice of hat is perfect: delicate, stylish, and just right for the look.

1950s Dior Look / 1950s fashion as seen in this 1950s photo of the Vintage Inn Blog grandmother, Betty who is wearing a 1950s dress and 1950s hat. — Vintage Inn Image Collection

Thank you for sticking around to the end—I hope you enjoyed this post as much as I enjoyed putting it together! There were so many fantastic photos of people wearing hats that a Part 2 is definitely in the works. Stay tuned!

Now, it’s question time: Are you a hat person, or do you prefer to go without? I’d love to hear your thoughts—feel free to share your opinions or let me know which hats were your favorites in the comments below!

Further Reading:

Vintage Easter Blog Posts (archived collection)
Easter Parade-Toronto’s oldest tradition that is really all about the Hats!
Do You Have An Easter Parade Hat?
Vintage Photos 1920s-1960s (archived collection)

Thanks for dropping by!

Liz

Brief History of the Christmas Brooch & Christmas Corsage

Victorians wore special brooches at Christmastime, often made of high-karat gold and precious jewels.

Christmas corsages became fashionable in the 1940’s. The term corsage means “bodice of a dress”. According to a corsage making manual from the 1920’s, “a corsage does not just indicate an occasion, it also gives an air of importance”. For the well-to-do, a true corsage was always made from real flowers, like roses, violets, orchids and other organic decorations like ferns and feathers

The more frugal minded, creative women created their own, or purchased a less expensive versions, of holiday corsages. These often-contained items made of plastic leaves, paper flowers, bells, snowmen, Santa faces, reindeer, angels, bits of ribbon and cord. and anything else, that was a reminder of the season (Source).

Christmas pins developed from the Christmas corsage. It was during the 1940s that the first Christmas brooches began to be mass-produced in America (but they existed before this time). This again was an era of industrialization, and many of the well-known costume jewellery designers originated during this period, and proliferated throughout the course of the 20th century. Christmas in America took a more secular turn, and designers now had a wealth of iconography from which to choose. You will find brooches in the shape of snowflakes, angels, reindeer, sleighs, bells, stockings, Santa hats, presents, candles and wreaths etc., etc. The most popular being the Christmas tree (of course!).