Cool doesn’t mean who has the latest gadget and it’s not the person who’s ahead of the curve when it comes to music. It’s time to look at some old school cool and remember exactly what it means.

The still-cool Harrison Ford

1Sean Connery just chilling


Clint Eastwood, Olive Sturgess and Dani Crayne being cool in San Francisco in 19542

Pulling off a suit with impeccable cool, Cary Grant23

None of us will ever have as much style as Jimi Hendrix

Michael Caine, rocking these glasses before they were ‘cool’21

This train doesn’t get cooler. Paul McCartney sitting opposite Mick Jagger20

Even his mugshot is cool, David Bowie19

Queen Elizabeth and Prince Phillip, cool at the horse races18

This cool couple from 197517

Frank Sinatra steps out of a tiny helicopter, drink in hand16

Leather-clad biker chick15

Here are the Beatles before they were famous14

Some casual graffiti from this man in a suit13

Nothing is cooler than these Jamaican kids posing for a photo12

A women’s rooftop boxing match11

Kids from Chicago in the forties10

This gif of Marlon Brando is just too cool. From his screen test for Rebel Without a Cause in 19559

Elspeth Beard, the first woman to circumnavigate the world by motorcycle. This was taken just after her 3-year, 48,000 mile trip.8

Paul Newman looking effortlessly cool while boating in Venice in 19637

Diana Rigg plays Olenna Tyrell in Game of Thrones. Cool then, cool now.6

Was your first car as cool as this?5

Greasers in New York City in 19504What’s your definition of cool?