Hats have always been the crowning item in a man’s wardrobe. Chiefs in primitive cultures wore elaborate headdresses to identify themselves as leaders of their clans. Jewel-encrusted crowns have been popular with monarchs for millennia. And hats were so familiar as symbols of status to the ancient Romans that newly freed slaves received special hats to make sure they could move about as free men.

In the Western world, felt, leather, fur, and straw have long been the most common materials used by hatters. In the Middle Ages and the Renaissance, lower-class men in many areas of Europe were forbidden from wearing furs or fine embroidery, and their headwear reflected these laws. Commoners’ hats of this time were often made of felt or skin and looked like caps. Courtiers’ hats, however, were wide, with feathers, embroidery, and jewels. These hats were less practical and more symbolic, with no well-defined brim to shade the eyes or ward off the elements.

It was in the mid-1500s that headwear began to get noticeably taller. Caps were still worn by the lower classes, but taller, brimmed hats, adorned with feathers and made of felt, beaver, or other soft skins, were popular with the wealthy from about 1550 onward. The 1600s saw wider brims in men’s hats, morphing into the Puritan-style wide brim we associate with the pilgrims and Plymouth. Men in France and Spain wore wide, upturned brims like those immortalized in The Three Musketeers.

Brims became narrower in the 1700s, notably in France. Tricorne hats, like those worn by soldiers in the Revolutionary army, were popular with the upper classes. The lower classes wore them as well, though in leather or felt, and without the plumes of the aristocracy. In the second half of the 18th century, the modern top hat began to emerge in England, where relatively narrow-brimmed hats with high, rounded tops became fashionable in the 1780s. The opposite was true for the European and American peasantry, who wore wide brims and low tops, spawning what would become the cowboy hat.

By about 1820, the top hat had virtually replaced the traditional tall English hat. The top hat was worn by all classes of men for all occasions. Variations ranged from simple cylinders to hats with curved sides and upturned brims.

Top hats in various styles would remain popular until 1849, when London hatter William Bowler changed the style drastically by designing a short, rounded hat meant to be worn to the races. In England, the hat was called a bowler, after its creator, but in the United States, the hat became known as a derby, for its association with the track. The bowler was common among all classes for most of the Victorian era, while the top hat was preferred by the upper classes and for formal occasions.

The lower classes of this period often wore caps that we think of as Irish-style or newsboy caps. These were made of felt or tweed wool, and were often made in plaid or herringbo...

In America, different stylistic innovations were afoot. By the second half of the 19th century, cowboy hats were a well-established style. One name in the hat business from that era that is still a powerhouse today is Stetson. Founder John Stetson is said to have got his start in the hat business when he made himself a wide-brimmed beaver-felt hat for a hunting trip. These hats were light and easy to make, requiring no tanning of the material.

Soon Stetson founded his company and popularized the style among cowboys, gentlemen, and even the U.S. military. He called his hat "Boss of the Plains," after his time hunting and working in the American West. The "Boss" was soon the standard for western wear, and Stetson was forever synonymous with the word "hat" in America.

With the rise of industrialization in Western Europe and America, men could afford to own more than one or two hats. Seasonal hats quickly became the rage. In the spring and autumn, men wore derbies or similar hats with a scrunched peak, often called a trilby. Top hats were worn in the winter, and a major innovation in summer wear came at about the turn of the century—straw hats.

The most popular straw hat was the Panama. Men valued them for their elegant style, lightweight construction, and cooling straw weave. A more American and European variation on the straw hat is the straw boater, a low, flat-topped hat with a wide brim and a colored band. At the turn of the 20th century, this was the hot summer look.

Fedoras appeared in the 1920s. This medium-wide brimmed hat with a pinched front became the standard headwear for men throughout the year, though the bowler was still preferred by some. Varying styles of the fedora and trilby continued to emerge. For example, the flat-topped pork pie hat became connected to jazz and blues culture. Then there was the homburg, which was almost the same thing aesthetically as a fedora, except its brim was stiff and fixed rather than bendable.

As the 20th century drew to a close, the brims of hats became smaller, and by the 1960s, hats were no longer a necessary part of everyday fashion at all. To the consternation of many, baseball caps and Irish-style caps replaced many types of more formal men’s hats. In recent years, though, the fedora, pork pie, and trilby have seen a resurgence of popularity among younger generation, for whom all things old are often the most hip.

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