30 Vintage Photos That Show That Our Grandparents Were Actually Really Cool

Hats off to these pioneers of old-school cool.

1950s male teen greaser smokes cigarette, cool grandparents
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It's easy to forget that our grandparents didn't just come out of the womb as seventy-somethings with hard candies in their purses and long-winded stories. No, back in their heydays, grams and gramps had a whole lot of swagger. They rode motorcycles, bent the rules, and frolicked on the beach—all while wearing the coolest shades. Really, if you ever stopped to take a look at some of your grandparents' old photos, you'd likely find that your folks' folks were pretty darn cool. Keep scrolling to get a glimpse of some old photos from the 1940s, '50s, '60s, and '70s that prove just how fun and fashionable our grandparents (and great grandparents!) were. And for more fun vintage pics, check out these 17 Vintage Family Photos That Will Make You Laugh.

1
This vinyl-obsessed teen

 1960s teen girl sits upside down on chair, cool grandparent
H. Armstrong Roberts / ClassicStock / Alamy Stock Photo

The perfect ponytail. The ear-to-ear grin. The single loafer on the floor. We're sure this grandma was the coolest girl in school in the 1950s.

2
This dreamy Danny Zuko

1950s male teen greaser smokes cigarette, cool grandparents
INTERFOTO / Alamy Stock Photo

This grandpa was the epitome of a bad boy. Well before Grease, this 1950s teen was rocking an impressive pompadour and a mysterious cut on his face.

3
These beach babes

Two 1950s female teens reach for beach ball in male teens hands on beach, cool grandparents
H. Armstrong Roberts / ClassicStock / Alamy Stock Photo

Someone's paw-paw was playing hard to get back in the 1950s. And he looked super suave doing it.

4
This toned twosome

couple walking on beach cool grandparent photos
Alamy

Long before grandpa's preferred attire was a suit and tie, he and grandma were just another couple of cuties wearing little more than swim trunks and smiles in the '70s on the beach.

5
This incredible dog whisperer

A Woman Water Skiing with her dog
Alamy

Oh, you taught your dog how to sit and stay? That's cool and all, but in the 1970s, this grandma literally taught hers how to WATER SKI.

6
This smooth cowboy

Grandpa Posing with a Cowboy Hat Old Photos of Grandparents
Reddit/adventurethyme_

"Grandpa's got swagger!" one user commented on Redditor adventurethyme_'s photo of their grandfather posing in 1958. We couldn't agree more.

7
This cool quarterback

Grandma in the 1970s Playing Football
Reddit/tsugaikogarashi

Tom Brady, who? This '70s photo of Redditor tsugaikogarashi's grandma certainly makes a case for women in the NFL.

8
This suave pair

A Couple at a Party in the 1970s
Alamy

Alamy

Bare feet, long lashes, oversized earrings, and undersized everything else makes this lady about as cool as they come. And has anyone ever looked as good as this gent does drinking a Coca-Cola? We think not.

9
This cool couple

couple smoking cool grandparent photos
Reddit/2g00d2btru3

If dating in our grandparents' day was supposed to be about giving corsages and holding hands, then Redditor 2g00d2btru3's grandparents were serious rebels back in 1960.

10
These shaggy stunners

1960s hippies gather in London's Trafalgar Square, cool grandparents
Alamy

Look at these teenagers hanging out in London's Trafalgar Square with nothing but a pack of cigarettes, a banjo, a guitar, and a whole lot of hair.

11
This tiny dancer

1950s young dancers crowd the floor for a rock n roll dance, cool grandparents
Trinity Mirror / Mirrorpix / Alamy Stock Photo

This grandma simply could not be cooler. With her mod haircut, her high-waisted skirt, and her carefree moves, it's clear she had it going on.

12
This ride-or-die duo

1970s couple rides motorcycle, cool grandparents
Alamy

Who needs shoes when you have epic shades, '70s stripes, an awesome bike, and your number one gal?

13
These groovy kids

1970s Couple at a Concert
Alamy

Here's proof that dancing in our grandparents' day wasn't all Lindy hopping in poodle skirts.

14
These psychedelic riders

Hippie Van in the 1960s
Alamy

Who do you think pioneered flower power? Our grandparents, of course!

15
This rockin' grandpa

man playing guitar cool grandparent photos
Reddit/peter_pater

Between the western shirt, choker necklace, and pinky ring, Redditor peter_pater's grandpa has got so much swagger that we'll even forgive him for that mullet.

16
These skating sweethearts

couple roller skating cool grandparent photos
Alamy

If you thought perfecting the Harlem Shake was hard, imagine trying to do the Hustle on skates.

17
These jive junkies

1950s young couple jive dancing, cool grandparents
Trinity Mirror / Mirrorpix / Alamy Stock Photo

Grandpa is feeling himself on the dance floor—and we don't blame him.

18
This trendy trio

1970s London model gawked at, cool grandparents
Keystone Pictures USA / Alamy Stock Photo

In the 1970s, this grandma was showcasing the future of fashion. And somehow, she even makes that foil helmet look good. Get it, grams!

19
These spring breakers

Students on Spring Break at the Beach 1960s
Alamy

No one is sweatin' anything in this car. This group had a far cooler spring break than anyone heading to Cancun today.

20
These grazers in the grass

1960s teens relax in meadow, cool grandparents
Roman Nerud / Alamy Stock Photo

We can't get enough of these grandmas with their high-tops, cuffed shirts, cardigans, and too-cool-for-school attitudes.

21
These gender benders

Vintage Photo of Grandparents Dressed in Each Other's Clothes Old Photos of Grandparents
Reddit/dahlek88

Even in the 1940s, girls—and Redditor dahlek88's grandpa—just want to have fun.

22
This dapper driver

Grandpa Posing with his Chevrolet Old Photos of Grandparents
Reddit/denzeljoysonlmao

Getting a new car is a teenager's dream. But just imagine how awesome it must've been for this dashing young man to get his ride in 1952. According to Redditor denzeljoysonlmao who posted this photo, their grandpa was the first person in his hometown in India to own a car back in the '50s.

23
This threatening mother-in-law

woman with shotgun cool grandparent photo
Reddit/SuchGo

"If you hurt her, I'll kill you" isn't just an empty threat in some families. Redditor SuchGo posted this photo with the caption: "A picture from my grandparents' wedding album that I'm obsessed with of my grandpa's MIL threatening him to be good to my grandma." In short, these grandparents are cool, but the great grandma is even cooler.

24
This mover and shaker

men and women dancing cool grandparent photos
Alamy

Long before there was dabbing and flossing, our grandparents were getting low.

25
This daring duo

woman on man's shoulders cool grandparent photo
Reddit/4Redrocket

Between grandma's swimwear and the stunt she's doing in it, this 1930s picture from Redditor 4Redrocket proves that being in love makes you do reckless things, no matter the decade.

26
These splish-splashers

Vacation in the 1950s at the Beach Old Photos of Grandparents
Alamy

Today, even Taylor Swift would rock one of those high-waisted bikinis. But grandma did it first.

27
This proud pilot

Grandpa Flying Around in a Plane Old Photos of Grandparents
Reddit/mjohnson231

This grandpa used to double as his family's very own personal pilot. Redditor mjohnson231 uploaded the above photo and noted that it was taken of her grandfather "after flying my aunt around in his plane." Talk about a sweet ride!

28
These lounging ladies

women in hats cool old grandparent photo
Reddit/CanardLaque

Who says that menswear is a recent trend? From the overcoats to the tipped hats, these women (including Redditor CanardLaque's great grandma) were bringing some serious style back in the day.

29
These sunbathing beauties

women on car cool grandparent photo
Reddit/quantanaut

The 1955 Miss Curvette pageant in Newburgh, New York featured Redditor quantanaut's grandma. Lookin' good, ladies!

30
This motorcycle 'ma

A BAMF Grandma on a Triuph Old Photos of Grandparents
Reddit/TheEricEllis

And finally, check out Redditor TheEricEllis' absolutely incredible grandma posing with her Triumph motorcycle in the '50s. You go, grandma! And for more nostalgic photos, check out these 20 Photos Only Kids Who Grew up in the 1980s Will Understand.

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