22 Photos Show Us The Real Meaning Of ’Old School Cool’

Step into a time machine and journey back to the days of old-school cool. When it comes to style, attitude, and pure coolness, few eras can rival the iconic decades of the 20th century. From the dapper sophistication of the 1920s to the rebellious rock ’n’ roll swagger of the 1950s, the past was full of unforgettable moments and unforgettable people.

1. “My great uncle Bill in 1952 at age 18 to today at age 87.”

2. “My grandpa’s got game, c. late 1940’s.”

3. Like father, like daughter

4. Maud Wagner, the first known female tattoo artist, appropriately covered with tattoos.

5. “My grandparents’ honeymoon in Switzerland, 1946.”

6. “My weightlifting great-grandpa holding my grandpa over his head”

7. “My grandfather and a buddy on the beach in Hawaii...with matching zebra swimsuits”

8. “In those times, nothing mattered except who could fly the highest.”

9. "He’s the personification of the ’80s. He is the ’80s!

10. A flight instructor for the Canadian Airforce enjoying a rare moment on earth

11. “My grandad and his goat named Sarah having their daily playful boxing fight.”

12. “My grandma ironing in her mink coat.”

13. “This explains why I’m the most uncool person ever because my mom took it all! Oh, and that bike? She built it.”

14. “My parents on their honeymoon with matching sneakers.”

15. Louis Armstrong playing for his wife at the Pyramids of Giza.

16. “My mom in NYC, when she sailed around the world.”

17. “Me and my buds hamming it up on mt. McDuff 1977.”

18. “No, it’s not a spa capsule. It’s a boat. A transparent boat. Yeah...”

19. “My grandfather invented the selfie in 1961.”

20. “My mom in the early ’50s rocking a peasant blouse and pearls on a date with an American soldier”

21. “My mom and her friends on the construction site of the Sydney Opera House”

22. “My grandparents after climbing Mt. Fuji in Japan”

Don’t let the coolness end here! Keep the nostalgia train rolling and explore more fascinating topics from our website:

• 20+ Parents and Grandparents That Show Us Why Old School Is the Coolest School
• 21 Warm Family Photos That Are Beaming With Nostalgia
• 22 People Whose Parents Were the Definition of Cool