#1. A group of kids in Chicago .
#2. A couple show what elegance looks like [Michigan Ave., Chicago, 1975]
#3. A group of men enjoy ice cream [England, 1971].
#4. Models in nautical-inspired clothing. [1940s]
#5. A woman named Florette basks in the Monte Carlo sun 
#6. Two men at a tattoo parlor [1920s].
#7. Two ladies stroll at the beach [circa late 1920s]
#8. A figure-skating man in New York City. 
#9. A girl shows what deep, classic elegance means [Harlem, New York City, 1940s].
#10. One of Londons shopping districts .
#11. Model Bettie Page [1950s].
#12. A woman defines summer fashion with her vibrant look [California, 1950s].
#13. Katherine Hepburn, whom Time describes as a woman could care about her looks and still look like herself .
#14. Two girls draw attention as they walk the street of Cape Town, South Africa .
#15. Paul Newman shows how to look effortlessly cool [Venice, Italy, 1963].
#16. Three moga (modern) girls stroll a street in Kageyama Koyo, Japan .
#17. A woman shows retro elegance [Accra, Ghana, 1972].
#18. Brigitte Bardot showing she can make any hat look chic .
#19. James Brown, one of the classiest looks youll ever see. On the background is his Lear jet .
#20. Mia Farrow in London, the mid-60s epicenter of fashion and pop culture [ circa 1960s].
#21. Cary Grant, often referred to as the epitome of elegance [1950s].
#22. Retro beach fashion [1950s].
#23. Two men in dashing daysuits [circa 1910].
#24. Actor Toshiro Mifune demonstrates graceful presence [Venice, 1960].
#25. Jamaican immigrants in Tilbury .
#26. Style icon Audrey Hepburn in the film Two for the Road .
#27. Trudy Marshall, Jeanne Crain, Gale Robbins, June Haver and Mary Anderson .
#28. Marlon Brando in a coat and tie. He popularized the bad boy look [circa 1950s].
#29. Clint Eastwood, Olive Sturgess, Dani Crayne looking good on a sunny day [San Francisco, 1954].
#30. A swimmer demonstrates why old school is cool.
#31. A typical 60s prom.
#32. Natalie Wood looking timeless [photo date unknown].
#33. Models stand in line at Roosevelt Raceway .
#34. Roy Halston Frowick, one of the most prominent American designers of his time . One Billy Joel song goes, They were all impressed with your Halston dress.
#35. Irish farmers at a pub prove that you can look good in suits and rubber boots .
#36. Grace Kelly wears a smile with her glasses. Her timeless fashion style is constantly recreated.
#37. Erlin Ibreck impresses with a pastel dress [London, England, 1966]. She moved to the United States where she became successful despite overt racism in the fashion industry.
#38. Freddie Mercury riding Darth Vader while wearing a Flash Gordon shirt .
#39. A girl models in New York City .
#40. A boy in Boston dressed fashionably from head to toe .
#41. James Garner combines good looks with good taste .
#42. Two women at an event in Tehran, Iran [1960s].
#43. A model wears an ensemble by Balenciaga for Vogue .
#44. Londoners walking Carnaby Street .
#45. Models pose for a 1954 issue of Vogue.
#46. Grace Kelly at the Princely Palace of Monaco . She frequently posed with a purse while pregnant with her daughter Caroline, which would later on inspire the Kelly bag.
#47. Chinese-American actress Anna May Wong looking royal in a silk dress [1930s].
#48. A model wanders Disneyland .
#49. A model in Paris [1950s].
#50. A couple steal the floor at a Be-Bop cellar with their dance moves and style [Paris, France, 1951].
#51. Audrey Hepburn .
Now you know why cool rhymes with old school.