51 Vintage Fashion Photos That Reveal Just How Awesome People Used To Dress

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#1. A group of kids in Chicago [1941].

#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 [1953]

#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. [1937]

#9. A girl shows what deep, classic elegance means [Harlem, New York City, 1940s].

#10. One of London’s shopping districts [1908].

#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” [1938].

#14. Two girls draw attention as they walk the street of Cape Town, South Africa [1965].

#15. Paul Newman shows how to look effortlessly cool [Venice, Italy, 1963].

#16. Three “moga” (modern) girls stroll a street in Kageyama Koyo, Japan [1928].

#17. A woman shows retro elegance [Accra, Ghana, 1972].

#18. Brigitte Bardot showing she can make any hat look chic [1950].

#19. James Brown, one of the classiest looks you’ll ever see. On the background is his Lear jet [1967].

#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 [1948].

#26. Style icon Audrey Hepburn in the film “Two for the Road” [1967].

#27. Trudy Marshall, Jeanne Crain, Gale Robbins, June Haver and Mary Anderson [1944].

#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 [1958].

#34. Roy Halston Frowick, one of the most prominent American designers of his time [1960]. 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 [1963].

#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 [1980].

#39. A girl models in New York City [1956].

#40. A boy in Boston dressed fashionably from head to toe [1968].

#41. James Garner combines good looks with good taste [1959].

#42. Two women at an event in Tehran, Iran [1960s].

#43. A model wears an ensemble by Balenciaga for Vogue [1963].

#44. Londoners walking Carnaby Street [1966].

#45. Models pose for a 1954 issue of Vogue.

#46. Grace Kelly at the Princely Palace of Monaco [1962]. 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 [1961].

#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 [1962].

Now you know why “cool” rhymes with “old school.”

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