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.

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.

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!

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.

Source: Etsy-LightSilverAndPaper

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

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!

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

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!

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.

Source: City of Toronto Archives

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

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?

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.

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.

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.

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.

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

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

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!

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!

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.

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