There’s cool, and then there’s an “old school cool.” We’ve come a long way in the past decades, but sometimes we’ve forgotten what it’s like to be real classy and cool.
Let’s take a look at these 45 masters of old school cool. Enjoy!
1. Six-time Golden Globe winner Paul Newman boating in Venice during a film festival (1963)
2. Elspeth Beard, shortly after becoming the first Englishwoman to circumnavigate the world by motorcycle. The journey took 3 years and covered 48,000 miles.
3. Marlon Brando’s screen test in “Rebel Without A Cause” (1955)
4. The gorgeous necklines of the 1950s
5. Ernest Hemingway’s striking passport photo (1923)
6. An old family photo from the early 1900s
7. A salesman having his motorized roller skates refueled at a gas station (1961)
8. Queen Elizabeth and Prince Phillip at the horse races (1968)
9. Cosmos host and astrophysicist Neil DeGrasse Tyson at a college wrestling match
10. Clint Eastwood with actresses Olive Sturgess and Dani Crayne in San Francisco (1954)
11. The original way to ‘text’ in class (1944)
12. A young Sean Connery relaxing on the couch
13. A gang of greasers in NYC (1950)
14. Caroline Kennedy walks ahead while her father, the most powerful man in the world, carries her doll (1960)
15. Teenagers and their first car (1950s)
16. Diana Rigg (Olenna Tyrell from Game of Thrones) in 1967
17. Jack Nicholson from the film “One Flew Over The Cuckoo’s Nest” (1976)
AP Photo
18. Sophia Loren, one of the only actresses to win an Oscar, Grammy, and Golden Globe awards
19. Ellen O’Neal, the greatest woman freestyle skateboarder in the 1970s
20. A man ice skating in a suit (1937)
21. A businessman doubling as a graffiti artist
22. The Beatles before they were famous
23. This is how teenagers dated in the 1950s
24. Writer Hunter S. Thompson, Johnny Depp and Vincent Gallo during the 25th anniversary of Fear and Loathing in Las Vegas
KMazur / WireImage
25. Leather-clad English rocker girl
26. Frank Sinatra stepping out of a helicopter with a drink
27. On the way to Woodstock (1969)
28. Dean Martin & Angie Dickinson on the set of Rio Bravo (1959)
29. Girl with typewriter and a smoke
30. A couple on Michigan Avenue in Chicago (1975)
31. Novelist Raymond Chandler who created the cool detective Philip Marlowe (1946)
SFC
32. Wilt Chamberlain after setting the NBA record with 100 points in a single game (1962)
33. David Bowie’s mugshot
34. Muhammad Ali looking dapper
35. Paul McCartney and Mick Jagger sit opposite each other on a train to Bangor (1967)
36. F1 Timekeeper (1969)
37. A young Michael Caine in 1959
38. Brigitte Bardot visits Pablo Picasso at his studio near Cannes in 1956
39. A couple dancing in a 1950’s “Be Bop” theater as everyone looks on
40. Jimi Hendrix backstage at Monterey Pop Festival (1967)
41. The definition of old school cool. Cary Grant in the 1950s
42. Robert DeNiro and Al Pacino on the set of Godfather II (1974)
43. James Dean and his Porsche 550 Spyder
44. Evel Knievel’s famed jump over the fountains at Caesars Palace in Las Vegas in 1967; he was unconscious for a month afterward.
Las Vegas News Bureau
45. Theodore Roosevelt (1885)
Library of Congress