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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

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

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

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4. The gorgeous necklines of the 50s

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

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6. An old family photo from the early 1900s

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7. A salesman having his motorized roller skates re-fueled at a gas station, 1961

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8. Queen Elizabeth and Prince Phillip at the horse races, 1968

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9. Cosmos host and astrophysicist Neil DeGrasse Tyson at a college wrestling match

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10. Clint Eastwood with actresses Olive Sturgess and Dani Crayne in San Francisco, 1954

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11. The original way to 'text' in class, 1944

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12. A young Sean Connery relaxing on the couch

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13. A gang of greasers in New York City, 1950

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14. Caroline Kennedy walks ahead while her father, the most powerful man in the world, holds on to her doll, 1960

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15. Teenagers and their first car, 1950s

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16. Diana Rigg (Olenna Tyrell from Game of Thrones) in 1967

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17. Jack Nicholson from the film "One Flew Over The Cuckoo's Nest," 1976

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AP Photo

18. Sophia Loren, one of the only actresses to win an Oscar, Grammy, and Golden Globe awards

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19. Ellen O'Neal, the greatest woman freestyle skateboarder in the 1970s

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20. A man ice skating in a suit, 1937

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21. A businessman doubling as a graffiti artist

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22. The Beatles before they were famous

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23. This is how teenagers dated in the 1950s

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24. Writer Hunter S. Thompson, Johnny Depp and Vincent Gallo pictured during the 25th anniversary of Fear and Loathing in Las Vegas

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KMazur / WireImage

25. Leather-clad English rocker girl

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

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27. On the way to Woodstock, 1969

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28. Dean Martin & Angie Dickinson on the set of Rio Bravo, 1959

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29. Girl with typewriter and a smoke

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30. A couple on Michigan Avenue, Chicago, 1975

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

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SFC

32. Wilt Chamberlain shortly after setting the NBA record with 100 points in a single game, 1962

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33. David Bowie's mugshot

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34. Muhammad Ali looking dapper

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35. Paul McCartney and Mick Jagger sitting opposite each other on a train to Bangor, 1967

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36. F1 Timekeeper, 1969

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37. A young Michael Caine, 1959

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38. Brigitte Bardot visiting Pablo Picasso at his studio near Cannes, 1956

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39. A couple dancing in a 1950's "Be Bop" theater as everyone looks on

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40. Jimi Hendrix backstage at Monterey Pop Festival, 1967

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41. Cary Grant in the 1950s

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42. Robert DeNiro and Al Pacino on the set of Godfather II, 1974

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43. James Dean and his Porsche 550 Spyder

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44. Evel Knievel’s jumps over the fountains at Caesars Palace in Las Vegas, 1967; he was unconscious for a month after the stunt.

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Las Vegas News Bureau

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45. Theodore Roosevelt, 1885

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Library of Congress

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