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Iconic Hats
Newsboy Hats and Ivy Hats
Newsboy caps and ivy caps – variously known as flat caps, baker boy hats, driving caps, golf caps, English caps, eight-quarter caps, etc. – date to pre-World War I and historically are associated with the working classes.
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The Top Hat
If the bowler connoted a more democratic future, the top hat, most certainly represented, in the words of hat historian Colin McDowell, ". . . the power of political conservatism and the rule of the status quo." The top hat traces its origins to the tall sugar loaf hats of the late Middle Ages and Renaissance.
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The Fedora
Humphrey Bogart and James Cagney. Clark Kent and FDR: the Bowler and the Topper disappeared at the drop of a hat.  For most of the 20th Century, up until about 1960 when John Kennedy took off his hat at his presidential inauguration, men were not considered dressed for work without a hat.
 

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The Cowboy Hat
Although associated with the American West, the cowboy hat, arguably, is not an American creation. Arguably because there is no doubt that hats with big brims and large crowns had been popular in Mexico, coming to Mexico from Spain, well before "the American West was won". Historians trace the origins in Spain to the European invasions by the very accomplished horsemen from Mongolia.
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The Beret
Although worn as military headgear in ancient Greece, the modern origin of the beret is traced to the Basques, people living on both the French and Spanish sides of the Pyrenees Mountains. Centuries ago, the Basques were great fishermen and sailors, a fact that might explain the appearance of a very similar hat in Scotland.
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The Baseball Cap
The baseball cap in an American icon. It is in fact the only hat style that is an American creation. Its popularity in the United States received a big boost in the era of Babe Ruth, when baseball fans wore the cap as a badge of identification with their favorite team.
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The Bowler
When you picture Laurel and Hardy, Charlie Chaplin, a Rene Magritte work of art, the four major characters in Samuel Beckett's "Waiting for Godot", or a well dressed British banker, a bowler hat, known also as a derby, almost certainly comes to mind. The bowler, perhaps like no other hat before or since, stands unambiguously as a symbol for an age, a passage in western civilization.
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The Fez
The fez has a long and complicated history in the Middle East, Eastern Europe, and North Africa. I am not a historian and am not entirely familiar with the fez's nuances of meaning in these parts of the world. However, I do know this: for most Muslims, this hat is now politically incorrect.  
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