A good hat is like a billboard that instantly communicates to the world the interests and social standing of the wearer underneath. Whether it’s a silk spoon bonnet decorated with lace and organdy flowers from the mid-Victorian era or a weathered beaver-felt Stetson from the 1960s, hats tell us a lot of the people who wore them, as well as the styles and fashions of the day.

When the Victorian Era began in 1837, bonnets with large, hooded coverings that framed the face were made out of satin and silk. Wide-brimmed straw hats trimmed with handmade fabric flowers were also popular. By the 1850s, circular bonnets became more sculptural and stiff—a decade later, these drawn bonnets had become oval, framing the face more naturally than the round ones that had preceded them.

Straw skimmers, also known as rounds, were worn outdoors—the best of these had patterns of silk braids, real feathers, and other decorative embellishments sewn onto their tops. 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.

In the middle of the century, top hats came into prominence. One of the hat’s most famous customers was Abraham Lincoln, who favored stovepipes, as the tallest top hats were often called, for formal occasions. Meanwhile, magicians reveled in what they could hide (or appear to hide) inside their top hats (white rabbits), while authors such as Lewis Carroll created top-hat-wearing characters like the Mad Hatter.

Throughout the Victorian Era, particularly after the death of Prince Albert in 1861, mourning hats to go with mourning jewelry and similarly somber attire were common ways for women to express their grief. Some of these mourning hats included veils to hide the face.

On the other side of the Atlantic, a Philadelphia hatter named John B. Stetson introduced a hat called Boss of the Plains. With its wide, flat brim and straight-sided, round crown, the hat was an instant success with anyone working outdoors. It was a particular hit out West, where the short-lived era of the cowboy was in full swing.

Everyone from Custer riding to his doom at Little Bighorn to Canada’s North West Mounted Police wore Stetsons—the wide, flat-brimmed hats became the trademark of the Mounties in ...

Although Stetsons are associated closely with the Wild West, English derbies, also known as bowlers, were far more common. Black Bart wore a derby, as did Butch Cassidy and his gang. But good guys also donned bowlers—the Pinkerton detectives who eventually broke up the Jesse James gang all wore derbies.

South of the border, the Panama hat was finding an audience in Ecuador. Unlike boaters and bonnets, which took their shapes in part from the structural properties of their materials, Panama hats were more like straw versions of felt hats, from fedoras to derbies.

By the end of the century, women’s hats were moving in two directions. Some were demure, almost too small for the heads they were perched on. Others had high-domed crowns and were piled high with loops of ribbon and drapes of rich velvet. Wide Gainsborough hats, sometimes called cartwheels, were so heavily decorated with feathers that laws had to be passed to prevent entire species of birds from going extinct.

As the 20th century dawned, boaters were the hats of Vaudevillians, yachtsmen, and horseracing enthusiasts, while politicians favored Panamas—Theodore Roosevelt was 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.

In the Edwardian era, the Gibson Girl dominated fashion. The hallmark of the look was an hourglass figure and a big hat up top. Gainsboroughs were still worn, thanks to their popularization in the 1907 musical “The Merry Widow.” Smaller, but no less ornate, pompadour hats were a mirror of the popular hairstyle of the same name.

In the years before and after World War I, gigantic garden hats remained in vogue, but other trends were having an impact. Hats resembling berets and turbans began to appear, as did Musketeer hats. Tricorne hats, motoring hats, and straw boaters all had good runs toward the end of the decade. And as a precursor of the 1920s and the flapper era, close-fitting cloche hats were introduced.

For men of this era, the top hat was the unquestionable symbol of power and authority. Thus, J. M. Flagg’s famous World War I recruiting poster featured a version of Uncle Sam wearing a top hat. The hat fell out of favor after the stock-market crash, when it was associated with greedy fat cats, but it was revived in 1935 with the release of “Top Hat,” a film that gave audiences numbed by the poverty of the Great Depression a peek at the good life enjoyed by couples dancing cheek to cheek in top hats and tails.

Another popular men’s hat of the 1920s was the fedora—a medium-wide brimmed felt hat with a pinched-in front and a crease down the length of its crown. Until then, women were the fedora’s biggest customers, but in the ’20s men claimed the hat. In particular, the hat became a favorite of ruthless gangsters and the tough detectives that hunted them down.

Women in the 1920s went crazy for hats, especially the cloche. Cloche hats ranged from beaver felt dyed in a range of colors to tightly woven straw. At first, the brims of cloche hats were essentially extensions of the crown, dropping straight down on all sides with no rim, let alone brim. By the end of the 1920s, though, is was common for the cloche to be worn with the brim turned up, especially in the front.

Many cloche hats were worn unadorned, but lots of styles demanded ribbons, which could be tied to signal one’s availability to prospective suitors. A ribbon that resembled an arrow signaled that the woman was in a relationship, a knot meant the wearer was married, but a big bow was an eye-catching invitation.

In addition to the ubiquitous cloche, women wore sculptural hats resembling airplane wings or actual crowns. Felt hats were embroidered with Art Deco flowers, and kits were sold for just 89 cents so that women could make their own “crushers,” as they were called. Actress Louise Brooks made it acceptable to wear pokes and helmet hats, and so-called Speakeasy hats were studded with sequins and costume jewels.

Things sobered up a bit in the 1930s, but only a bit. Black, Sou’wester hats made of braided hemp continued the helmet look. In fact, straw hats went from garden to dressy, as straw cloches were woven with ecru to resemble smart tweeds.

Knit turbans took off thanks to Greta Garbo, the pillbox was introduced, and women even took to wearing sequined or rhinestone-accented calot caps, which resembled large yarmulkes and were first worn by the ancient Greeks. Colorful berets and pirate caps, as well as felt or stitched geometric Dutch Boys, added to the decade’s sense of style.

During World War II, the fedora reigned for men and women, mostly due to Ingrid Bergman’s look in the 1942 film Casablanca. Crocheted snoods designed to keep hair from getting tangled in machine parts were a counterpoint to Rosie the Riveter’s famous red with white polka dot headscarf. After the war, berets of crushed velvet and printed barkcloth gained ground, as did bandeaux, which weren’t really hats but looked like them from the front when padded and worn like a tiara.

Other hats of the 1940s included militaristic berets with platter-shaped crowns, small tilt or doll hats, bumpers of straw or felt, and increasingly exotic turbans, which had been popular in the 1930s and remained so during the war years. Some turbans were made of rich velvet and rose above the wearer’s head by as much as a foot. Other more humble creations were built out of cheap rayon and sold by Sears for 49 cents.

In the 1950s, hats almost resembled the costume jewelry of that period. The mushroom cloche and the melon hat were just two of the hats that took their shapes, and names, from food. Celebrities such as the Duchess of Windsor and Gloria Swanson wore casques, sailors, and large-brim hats interchangeably. Mamie Eisenhower wore an Air Wave hat to her husband’s first inauguration. Small, but visually arresting, cocktail hats were decorated with everything from dyed feathers to faceted beads, while bowlers, rollers, and Bretons were perfect for everyday wear.

Finally, in the 1960s, hats reflected the rising dominance of youth culture. The decade began with turban-like bubble toques made of feathers, prints, or mesh. Felt conehead caps and zippered Bobbie helmets exuded a Carnaby Street vibe, while fake fur was the fabric of choice for everything from pointed fedoras to pillboxes. Patent-leather jockey caps, from jet black to bright yellow, continued the Mod style. Even straw Gainsboroughs, which had been re-imagined as “flower power” sun hats littered with chenille daisies, now seemed entirely in step with the trend toward natural looks.

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