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Ushanka is Russian hat with round crown and ear flaps, usually made of fur. This hat is one of the symbols of the Soviet Union because it was developed and popularized in Russia during Civil War. Today ushanka is standard winter military hat in many countries, but also a fashioned hat made of different materials, not just fur.
On of the symbols of conquering the Wild West is, of course, Stetson Cowboy Hat. Because of its high quality it was a head gear of choice for all that roamed the planes of American West in 19th century. You can find out more about history of Stetson hats here.
Pork pie hat is round hat known from 19th century, called that because of similarity with that time pork pie dish. The most popular were from 1830 through American Civil War, but in the 20th century, it was popularized again thanks to actor Buster Keaton, and, after that, thanks to jazz musicians such as Lester Young and Charles Mingus.
Famous bowler hat, symbol of working but also upper classes as well, a better cowboy hat than a cowboy hat started as a hard hat for gamekeepers. You can read more about history of bowler hats here.