Vintage Photos That Prove Your Parents Were Way Cooler Than You

By: Kate Row | Last updated: Sep 28, 2023

It might be hard to believe but all of our parents had lives before we were born. While we know them as “mom” and “dad”, other people know them as the wild teenagers that skateboarded through the neighborhood and caused trouble. 

Check out these amazing vintage photos that people shared of their parents that remind us just how cool parents can be.

My Mom Skating Barefood and Unbothered

This perfect photo of someone’s mom skateboarding barefoot in the ‘70s just takes us right back in time. The wind in her hair and the dirt on her feet are such a sign of carefree and simpler times.


Source: Jsparks117/ Imgur

This photo from 1974 reminds us of simpler times. What’s a helmet and who needs one? She’s cooler than we’ll ever be, we must admit.

My Dad With the “Cool” Factor

This poster shared an amazing photo of their dad from 1980. From the fluffy hair and mustache to the tight shirt and cool car in the back, everything about this photo is iconic.


Source: Themasterofdonuts/ Reddit

We can’t ever hope to be this cool even if we could ride a horse like that. It looks like he’s even got the smolder going on straight off the cover of an old romance novel. Fabio who?

No Shoes, No Problem

While most of us probably keep the shoes on when we get on any kind of bike, it looks like shoes were utterly optional in the 1960s. This person shared this photo of their dad from the late ‘60s.


Source: CherryCherries/ Reddit

We find it interesting that he managed to wear gloves on his hands but nothing on his feet. Maybe shoes were just not groovy. Either way, this picture belongs on a magazine cover somewhere.

My Dad With the Car He Bought at 11-Years-Old

We don’t think we could have afforded a car on our lemonade stand earnings and allowances, but this person’s dad bought his very own car at the ripe age of 11!


Source: Godllu/ Reddit

He’s pictured here as a preteen in front of his 1939 Ford which he purchased with his own money from farming. Apparently, he also drove the thing himself, which could only be allowed in the ‘40s.

My Dad Whipping Out the Professional Moves

This person shared an incredible photo of his father pulling out the ‘70s movies on the skateboard. Why ride on your feet when you could ride on your hands? 

Source: Lilsebastian/ Reddit

We hope this photo is framed somewhere in their house because it certainly deserves a spotlight. We just hope he didn’t suffer any injuries with his face this close to the pavement.


My Dad: The Myth, The Legend

This man is clearly doing exactly what he loves and he’s doing it in style. We just feel lucky that this perfect moment was captured on camera for us all to gawk at. 

Source: Reallybadat/ Reddit

Now, he has 4 children and we can only hope he is still rocking these moves, and in short shorts, no less! We hope one or all of his sons will recreate this fantastic image.


That’s One Way to Teach

I don’t seem to remember my teachers having this much style when I was in class. But this person shared an amazing image of their dad teaching math in the late ‘70s or early ‘80s. 

Source: Icollectsausage/ Reddit

Naturally, this class was in Southern California, which seems clear by the way it looks like he’s riding a surfboard as he passionately teaches the kids a math lesson. A teacher like this would have definitely made me more interested in the subject.


Mom Taking Selfies Before They Were Cool

This person’s mom was taking selfies in 1989, way before they were cool. Not to mention, she was rocking the mirror self, an even more niche version of the photos we see all over social media today. 

Source: Cmajorlips/ Reddit

She was certainly ahead of her time. This is definitely one that her son or daughter should recreate.


Like Father, Like Son

This wholesome photo just warms our hearts. There is nothing sweeter than a son who wants to be just like dad. In this case, dad is a fighter pilot and the son is looking up to him (literally).

Source: Datingpuppy/ Reddit

He even has the ‘80s pilot jacket and is more than ready to fly. We have to wonder if that little kid grew up to be a pilot as well, following in dad’s footsteps.


Just Dad and Magic Johnson

Apparently, this person was looking through old photos when they stumbled across this random pic of their dad with a very famous basketball player. Yes, that is Magic Johnson in the arms of their dad!

Source: Ilikeblazing/ Reddit

Now, it doesn’t get much cooler than this! We’re surprised this was shuffled away in an old photo album. If we were their dad, we’d be boasting about this everywhere.


Broken Bones Won’t Stop Her

This person’s mom shared a photo of their mom skateboarding with a broken wrist, giving new meaning to that old saying “just rub some dirt in it”.

Source: Thestrokesfan1988/ Reddit

By the look of the smile on her face, she is non too concerned with broken bones when she has ramps to ride and places to be. Let’s just hope she didn’t break any more bones on that not-so-stable-looking skate ramp.


Take that, Boys!

Girls rule and boys drool. This person’s mom was proving that point way back in 1950. Here she is pictured with a mouthful of pie right before she was crowned the winner of a pie-eating contest.

Source: Talking_head/ Reddit

Every other contestant was a boy and she showed all of them what was up. Coolest mom ever!


Ryan Gosling, Is That You?

This person shared a photo of their dad in the ‘70 striking a pretty dramatic pose. If you couldn’t tell from the hat or the clothes, this was taken in Paris, France.

Source: Eluviane/ Reddit

What is even more striking about this photo is that he bears an uncanny resemblance to the heartthrob, Ryan Gosling! The person who posted said that Gosling might need a paternity test after seeing this photo.


Oh Captain My Captain

The mystery of this photo will remain a mystery because we truly don’t know what this person’s dad was doing fully clothed wading through a body of water. But, when asked about the context of the image, he gave the best answer.

Source: Atternedcollar/ Redit

His kid asked what he was doing and the dad simply responded, “Shooting an album cover. Duh”. And that truly is the only context we need to appreciate this one.


Mom and Dad Galavanting Around the Globe

This person had the pleasure of finding a wonderful photo that captured their parents’ young love. The two were apparently galavanting around Globe and stopped to take this photo in 1985. 

Source: Gallowboob/ Reddit

They were in Santorini, Greece, which is apparently the origin story of how the person who posted this came to be! What a perfect encapsulation of being young and in love.


Best Christmas Card Ever

This person’s dad can be seen atop the shoulders of his cousins in what would make probably the coolest Christmas card in the entire world. We can’t be sure how they even managed this incredible formation.

Source: Frenchyvonrichter/ Reddit

But, the person who posted this doesn’t think that the “cool” gene was passed down to them. We think they should give this photo a shot and recreate it with their own cousins or siblings.


The 16-Year-Old Who Won a GT500 (on accident)

The story behind this image is even more impressive than the image itself. Apparently, this person’s dad won that Shelby GT500 on accident! He is 16 in this photo and he entered himself into a contest at the local shoe store.

Source: Reddit

However, he was under the impression that he was entering to win a sports jacket that he had his eyes on. In all actuality, the contest was to win that stunning car behind him. He ended up winning and received his first car by chance in 1967. 


War Buddies

This man was stationed in Vietnam and their kid shared this amazing photo of him from 1966. Apparently, he had his own pet monkey as you can probably tell from the animal on a leash in his arms.

Source: Matthewlarn Reddit

We would love to know the story behind how he inherited that pet. It looks like he was an excellent friend to have around during the conflict. People just don’t have pet monkeys these days.


Rockband Before it Was Cool

Some of us might have similar photos or memories to this picture but in ours, we’re all playing rockband. This rockstar was playing the real guitar in one of the most “‘80s” style photos we’ve ever seen.

Source: Captain_chewbacca/ Reddit

The rockstar stance and fluffy hair are so reminiscent of the time period. Not to mention the basement decoration. We’re not surprised this pic was snapped in 1986.


Dad Setting Records After a Few Drinks

Apparently this guy had no idea he would be setting records when he and a few buddies headed out to sea to go fishing. But, despite throwing back a few beers, he managed to catch a huge tuna.

Source: Itsmedusa/ Reddit

In fact. When this was taken in 1972, this was a record-breaking tuna that he caught in Newfoundland. Not too shabby for dad. He should show the kids this picture when they’re claiming he’s not “cool”.


The Man Reaches New Heights

When you look through old photos of your parents you really never know what to expect. But, what you certainly don’t expect to find is a photo of your dad balancing on not one, but three unicycles.

Source: Slidenasty/ Reddit

Is one unicycle just not enough? Apparently not. This guy used to ride around on three stacked on top of each other in parades. We’re impressed, to say the least.


Looking Out for the Prom Date

What we love about this one is that there are probably so many people of all different ages that shared this same experience and probably have photos just like it. This snapshot of someone’s mom was taken in 1969 on her prom night.

Source: Carlosspicypeep/ Reddit

She’s gazing out the window in anticipation for her prom date to arrive at her house. Dressed and ready for perhaps the most exciting night of all of high school, we think this probably reminded her kids that she was a teenager once too!


Was This The Orignal Coca-Cola Bear?

The ‘50s were a much different time for more reasons than the style and music. Apparently, people were feeding bears back in the day as well! Someone shared this image of their dad hand-feeding a real-life bear on the side of the road.

Source: Melissamarie86/ Reddit

No one pictured seems to be too concerned with the deadly animal being so close to them. If you look close enough you’ll see that he is actually giving the bear some soda! Who knew bears like Coca-Cola as much as we do?


Someone’s Dad Was Trying to Be a Commercial Actor

This photo should be used as a vintage ad for Gatorade. This person found this pic of their dad who was a firefighter holding up this Gateraide can as if he was paid to do so.

Source: Beanermcbean/ Imgur

What’s really happening here is that the men are doing a controlled burn in the ‘80s. And he just so happened to be enjoying a refreshing Gatorade at the time. Gatorade should run him a check for this kind of promotion!


Dad Under Cover

Being in the FBI sounds like a very cool job, but this photo basically just proves it. It appears this image could have been pulled right from a movie! It’s really an image of someone’s dad in the 1960s.

Source: Xofermd/ Reddit

He was an FBI agent (if you couldn’t tell from the suit) positioned at the Bahamas Airport. The car and the suit make this a perfectly “cool” photo that proves he had a whole interesting life before he had kids.


Dad With His Furry Friend

As we’ve seen, people had some really interesting pets back in the day. We’ve seen a man with a monkey and a man feeding soda to a bear, but this one might be even more intriguing.

Source: Manwithprinciples/ Reddit

This is an image of a commenter’s dad taken in 1987. That pet in his arms is his beloved Patricia. And Patricia just so happens to be a fox, of course. What ever happened to good old cats and dogs as pets?


Mustaches and Short Shorts

If you needed to display what the ‘70s were in one image, this one might just do it. The old Mustang is a truly stunning car, but the dad pictured here really takes the cake. His afro, mustache, and aviators are too perfect.

Source: Malpup/ Reddit

Even more so, the bare feet and denim cut-offs are a look that we’re not sure we’d like to ring back or not. It was certainly an iconic look.


Beach Bumming

Before he was driving his kids to and from soccer practice, changing diapers, and helping with math homework, dear old dad was catching waves and beach bumming around.

Source: Elisabot

This photo was taken in 1989 and perfectly encapsulates the “surfer dude” energy. Apparently, he was sleeping on the beach for weeks at a time with a sleeping bag just t catch the perfect wave. 


Dad Vs. Cheetah

In a long list of pictures you don’t expect to see of your dad comes this image of the man squaring off with a cheetah. We can’t be sure why or how he came face to face with the fastest animal in the world.

Source: Errn1987/ Reddit

But, it appears wild animals were awfully easy to get close to in the ‘70s. We can only imagine him trying to wrangle this large cat: “Honey, can we keep him?”