Nothing tops a beautiful outfit like a perfect hat. Whether it’s a lacy headdress decorated with velvet and tulle from the mid-Victorian era or a wide-brimmed, "flower power" sun hat of chenille daisies from the 1960s, hats reflect and define the fashions of their day.

During the 1860s and ’70s, the popular drawn bonnets of the mid-19th century became oval, framing the face more naturally than the round ones that had preceded them. These spoon bonnets were decorated with ribbons, lace, and flowers made of organdy and silk. Straw skimmers, also known as rounds, were worn outdoors—the best of these had patterns of silk braids sewn onto their tops.

By the end of the century, 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 the exception to this general rule. These showy chapeaux were decorated with so many feathers that laws had to be passed to prevent entire species of birds from going extinct.

As the 20th century dawned, the Gibson Girl dominated fashion. The hallmark of the look was an hourglass figure (achieved by painfully tight corsets) 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. By the end of the century’s first decade, Edwardian fashions were in full swing, resulting in black velvet hats trimmed with ostrich feathers and velvet-and-silk flowers.

In the years before and after World War I, gigantic garden hats were still 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 decade to come, close-fitting cloche hats were introduced.

Women in the 1920s went crazy for hats. In addition to the ubiquitous cloche, some with wide swooping brims, some without, 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 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 str...

During World War II, the fedora reigned, 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.

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 many pointed fedoras. Patent-leather jockey caps, from jet black to bright yellow, continued the Mod style, and even straw Gainsboroughs, which now seemed entirely in step with the trend toward natural looks, returned to the fashion stage for yet another bow.

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