45 Vintage Photos of People Looking Cool

There’s cool, and then there’s “old school cool.” Sure, we’ve come a long way in the past decades, but sometimes we forget what it’s like to be really classy and cool.

Let’s take a look at these 45 people oozing with old school coolness. Enjoy!

1. Six-time Golden Globe winner Paul Newman on a boat in Venice during a film festival, 1963

2. Elspeth Beard, the first Englishwoman to circumnavigate the world by motorcycle. The journey took 3 years, covering 48,000 miles.

3. Marlon Brando's screen test in "Rebel Without A Cause," 1955

4. The gorgeous necklines of the 50s

5. Young Ernest Hemingway's striking passport photo, 1923

6. An old family photo from the early 1900s

7. A salesman having his motorized roller skates re-fueled 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 New York City, 1950

14. Caroline Kennedy walks ahead while her father, the most powerful man in the world, holds on to 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 pictured during the 25th anniversary of Fear and Loathing in Las Vegas

KMazur / WireImage

25. Leather-clad English rocker girl

26. Frank Sinatra nonchalantly steps out of a helicopter with a drink in hand

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, Chicago, 1975

31. Famous novelist Raymond Chandler who created the cool detective Philip Marlowe, 1946

SFC

32. Wilt Chamberlain shortly 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 sitting opposite each other on a train to Bangor, 1967

36. F1 Timekeeper, 1969

37. A young Michael Caine, 1959

38. Brigitte Bardot visiting Pablo Picasso at his studio near Cannes, 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. 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 jumps over the fountains at Caesars Palace in Las Vegas, 1967; he was unconscious for a month after the stunt.

Las Vegas News Bureau

45. Theodore Roosevelt, 1885