In the first decades of the twentieth century there were so many different kinds of hats that a man could truly wear a hat for nearly every occasion. And, if he wanted to be considered a gentleman, he absolutely could not go without a hat. The cultural traditions favoring headwear for members of both sexes were very strong. Hat wearing would eventually go out of style by the second half of the century, but in the years between 1900 and roughly 1950, hats were an essential part of a man's wardrobe.
Headwear came in two basic styles: the hat and the cap. Caps were made of a soft fabric, usually wool and wool tweed but sometimes another fabric, and were generally brimless and sat close on the crown of the head. Caps were generally favored for more vigorous outdoor activities and for motoring, or driving a car. More common and far dressier than the cap was the hat, made of a heavy and almost always stiff material such as felt or straw, with a distinct brim and a crown that stood away from the top of the head. Hats came in a variety of styles, with the primary differences coming in the size and shape of the brim and crown, the material, and the color.
The most popular hat in the years up through World War I (1914–18) was the derby, called the bowler in England. Usually made of black or brown felt, with a round crown of moderate height and brim that was curled up all the way around, the derby could be worn for nearly every occasion but the most formal. Two other felt hats, the homburg and the fedora, were also very popular, multipurpose hats. The homburg was fairly formal, with a slightly curled brim and an indent running the length of the crown. The fedora was a flamboyant hat, with multiple indents in the crown and brim that could be snapped up or down, giving it the nickname "snap-brim."
The hat of choice for formal occasions was the top hat, a flat brimmed hat made of black silk, with a taller, straight-edged crown. Top hats were often worn with a hatband, a narrow band of fabric in a contrasting color that sat at the base of the crown. Another specialized hat was the panama hat, a wide-brimmed, stiff straw hat with a high crown typically worn only in the summer. A variation on the panama hat was the sailor hat, which had a low, flat cylindrical crown and a two-inch or wider brim. With the vast number of hats available, many of them in a range of colors, men could always find a hat to match their outfit and the occasion.
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Payne, Blanche, Geitel Winakor, and Jane Farrell-Beck. The History of Costume. 2nd ed. New York: HarperCollins, 1992.
Schoeffler, O. E., and William Gale. Esquire's Encyclopedia of 20th Century Men's Fashions. New York: McGraw-Hill, 1973.