If you’ve ever wondered what winter looked like in the 20th century, from the roaring 1920s to the 1960s, a nostalgia-filled collection of vintage winter images will transport you back in time. From bustling city streets blanketed in snow to rural winter scenes and everyday life in and out of the home, these images capture the special moments of winter past.

This post is also a part 2 to my 2016, ‘vintage 1940s & 1950s images of people spending time outdoors during the winter time’. It was a fun post to do, so let’s step back into a winter wonderland one more time…

Source: Etsy-LightSilverAndPaper

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1920s-1960s Vintage Photos of Winter Time Life

If you must take a photo in the snow, you might as well make it stylish.

1920s vintage photo of two women in 1920s winter fashions / winter coats and cloche hats posing outside in the snow.

Source: Etsy – maclancy

“Can teddy come out to play in the snow too mom?”

Adorable 1930s vintage photo of a young girl and her teddy standing in the snow with her mom beside her holding teddies hand. Cute winter style!

Source: Etsy-LightSilverAndPaper

Sometimes you just don’t want to be cold while you wait for someone to take your photo, so off to the photobooth you go!

Our lovely 1920s or 1930s lady with the pretty hair is looking longingly into the camera with a winter landscape behind her.

Source: Etsy – JakeRoeBucks

Here is another winter landscape photobooth image featuring a fashionable woman showing off her purse, but this time it’s from the 1940s.

Maybe this is the same photobooth? (P.S. It’s not)

Source: Etsy – JakeRoeBucks

1930s winter street scene of man wearing pawnbroker sandwich board in New York City.

Further Reading: Vintage Photos of New York City-In all it’s Splendor

Source: Art.com

Time to hit the Slopes! 1930s photo of a young woman holding her skiis ready for a day of winter fun.

Source: Etsy-LightSilverAndPaper

In my childhood / teenage years, I was a downhill skiier and was lucky to have travelled to many wonderful places to enjoy this winter sport with my family. So when I see cool photos like this one of our lovely 1940s lady enjoying the ski slopes (and our 1930s woman above), I just have to share!

Further Reading: Vintage Ski Posters 1930s-1950s

Source: Etsy – DearMacyVintage

Okay ONE more photo of women skiing from the 1940s. How adorable are these ladies with their stylish ski suits, well styled hair and cute winter hats? The answer is..adorable!

I love the lady on the rights, sweater jacket.

Further Reading: Ladies Winter Hats-1940s Style

Source: Etsy – JakeRoeBucks

Winter Stinks! An unhappy man shoveling snow in his driveway. 1940s vintage photo.

Source: Etsy-AlaskaVintage

A little fun during WW2-4 men in uniform posing with giant snowballs.

I think they are on leave as the middle man is holding a camera, so they are most likely out and about having a good time. -1940s photo.

Source: Etsy – JakeRoeBucks

If you manifest it, it will happen.

Two women posing beside the very tall snowman they built. -1940s photo.

Source: Etsy – JakeRoeBucks

1950s image from 1958 of 4 boys on sleds with two dogs getting ready to go down a hill for some winter fun!

Source: Etsy – maclancy

March 1957-Vintage photo of a woman posing in the snow in a hand knitted sweater.

Source: Etsy – iloveyoumorephotos

1950s game of hockey on the pond that has frozen in the backyard.

Can’t have the winter season without hockey (at least here in Canada)!

Source: Etsy-therescuedphoto

1960s photo of a husband and wife posing outside of their winter cabin as the man heads off to do some cross country skiing.

Source: Etsy-AlaskaVintage

I hope you enjoyed these vintage winter photos and if it stirred up some memories please shre in the comments section below. I love hearing from my readers!

Further Reading: Vintage Photos 1920s-1960s (Archived blog posts)

Thanks for dropping by!

Liz