Straw hats are a casual and carefree form of headgear in the West, suggesting idle summer days when a cool covering to protect the head against the sun is a requirement of civilized society. In other cultures, though, such as those in Asia, straw hats are used for the same protective purposes, but the wearers are usually workers toiling in fields.

Because of the wide availability and low cost of straw and grass, which can be plaited to create cordage known as sennit, straw hats are thought to be one of the oldest types of hats. European artwork from the Middles Ages depicts people wearing straw hats, while palm-leaf hats in Central and South America date even earlier.

By the 18th century, well-to-do European women had embraced the country styling of straw hats. The peasant look became fashionable, as wide-brimmed straw hats and high-crowned st...

In England, especially in the Bedfordshire area about an hour’s drive north of London, straw hatmakers became a powerful industry that was intensely competitive with woolen hatmakers farther north. Like woolen hats, straw hats were blocked and formed in traditional shapes. There, though, the similarities ended, since straw hats were more conducive to naturalist looks than their felt counterparts.

By the 1870s, small straw bonnets and wide-brimmed straw hats alike were loaded up with feathers and other decorative embellishments. At the same time, simple straw boaters with flat tops and brims came into vogue for both men and women. The origins of the design are difficult to pin down, but the Venetian gondoliers, who tied brightly colored ribbons around the crowns of their hats, were probably their inspiration.

Around the same time, on the other side of the Atlantic, another straw-hat industry was finding its footing in Ecuador. There, the Panama hat was born.

Unlike boaters and bonnets, which took their shapes in part from the properties of their materials, Panama hats were more like straw versions of felt hats, from fedoras to bowlers. They were woven from Toquilla plant fibers, which could be blocked and shaped into styles such as the Optimo, a straight-sided crown, with a ridge running down the length of its top. A good one could even hold water.

As the 20th century dawned, boaters were a requirement for Vaudevillians, yachtsmen, and horseracing enthusiasts, while politicians appeared to favor Panamas—Theodore Roosevelt was famously photographed wearing one in 1906 on a visit to the Panama Canal. By then, many of these hats featured black bands, which had graced Panama hats since the 1901 death of Queen Victoria.

Naturally these hats entered the culture. Just as Fred Astaire’s “Top Hat” had cemented the top hat’s reputation as a mark of elegance and sophistication, plays like “The Music Man,” which was made into a film in 1962, placed the straw hat in our collective consciousness as attire for hucksters and con men.

Men are usually associated with Panamas and boaters, but women took to straw hats, too. In the late Victorian period, straw cloth was often made into simple spoon bonnets, which were then decorated with artificial flowers. White straw bonnets were frequently adorned with embroidered netting on their wide brims. As for the color of all this straw, it ranged from blackberry to lilac.

During the Edwardian era, straw hats for women were worn for playing tennis, while in the 1920s, flapper-style cloche hats woven of straw were considered every bit as smart as those formed of felt. Sometimes the brims of these hats would extend straight downward, accentuating the hat’s bell shape. Other times, the hats would be worn at rakish angles, with upturned brims to reveal the eyes, or maybe just one.

Umbrella-brimmed sun hats in bonnet and skimmer styles were soon the summertime rage. By 1939, many of these hats would be known as “Gone with the Wind” hats, named after the wide hats worn by that film’s heroine, Scarlet O’Hara. Schoolgirl boaters tied with wide black ribbons were also fashionable, as were hats in the Queen Anne style, which featured a wide brim in the front that tapered to a narrow width in the back.

By the 1940s and ’50s, straw bowlers and ones made out of brightly colored cellophane straw gained currency. High-crowned straw hats were also popular during these years, in colors ranging from crimson to black. And by the 1960s, hatters were producing dome, beach, and cloche hats in creams, lacquered hues, and patriotic blends of red, white, and blue.

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