15 Old-Fashioned Hats Ready for a Comeback

Whether we wear them to stay warm, protect our heads, hide our hair, or simply add flair to our ensembles, hats have always been a celebrated part of our wardrobes. In honor of National Hat Day, here are 15 once-iconic toppers that have fallen out of fashion—and should be brought back into style.

1. The Snood

Don’t call this knotted headdress a hair net—it’s actually a snood. In the late 1850s and early 1860s, it was in vogue for young women to hold their hair back with close-fitting, bag-shaped caps they’d woven from velvet, lace, yarn, or other materials.

The trend faded by the 1870s, but the snood made a comeback in the 1940s after female factory workers realized it added both practicality and panache to their work ensembles. The hat fell to the wayside once more after World War II ended and women returned to the domestic sphere.

2. The Cartwheel hat

Resembling a flying saucer affixed to one’s head, the cartwheel hat is a wide-brimmed circular or saucer-shaped topper that first became popular in the 1930s. It was typically worn at a rakish angle, and it was usually fashioned from materials like straw, felt, silk, or taffeta.

To our modern sensibilities, the cartwheel hat may seem bizarre, and records indicate that the look also perplexed the public when it was first debuted. “Do not be astounded if you notice a smartly gowned woman crowned with a hat of huge proportions, for she is but following fashion’s latest edict,” one 1914 newspaper article noted. “The new large hats are broad brimmed and have low crowns, which are not discernible when the hat is worn, hence they resemble cartwheels tilted at a becoming angle.”

3. The tri-corner hat

If you’ve ever seen a portrait of George Washington, chances are good that he was wearing a tri-corner hat, or a tricorn. 17th-century European and American men of all social classes wore these hats because the brim turned up on three sides, allowing them to show off their stylish wigs. The hats were also small, which allowed polite gentlemen to take them off and tuck them underneath their arms when entering a building.

Tricorners were either left plain or festooned with feathers, brocades, silks, or metallic fabrics. They often came in neutrals like black, grey, and tan.

4. cloche hat

Famous flappers were fans of the cloche—a fitted, bell-shaped hat that took Roaring Twenties style by storm. Invented in Paris, the cloche became popular among both European and American women during the 1920s. The hat fit neatly over a short bob, and its simplicity allowed the era’s “modern women” to dance, socialize, and move with abandon.

Today, women occasionally wear cloche-like styles. However, the hat still remains synonymous with the Jazz Age.

5. The bowler hat

In 1849, London hat makers Thomas and William Bowler created a toque that gamekeepers on horseback could wear to shield their heads from low hanging branches. With its close fit, low crown, and sturdy make, the bowler hat was way more practical than a top hat.

Over time, businessmen, politicians, and celebrities became fans of the look. By the mid 1950s to 1960s, it was common for men to incorporate bowler hats into their suited ensembles. The look became less common by the 1980s. However, British cavalry officers still traditionally wear bowler hats and suits for their annual parade.

6. The coonskin cap

While it’s a myth that Davy Crockett wore a coonskin cap, they were indeed popular among American frontiersman during the late 18th century. Early pioneers saw Native Americans wearing the warm, fuzzy hats, and they adopted the look for themselves. Soon, the coonskin cap became inextricably linked with the rugged, individualistic American settler.

Like all iconic looks, changing cultural aesthetics caused the coonskin cap to dwindle in popularity. By 1902, the fuzzy hat wasn’t perceived as “rustic”—it was straight-up redneck. However, the look exploded in popularity once more when a TV show based on Crockett’s adventures premiered in 1954.

Crockett fever faded in the 1960s, and the cap once more became a relic of a bygone era. However, bloggers report that a few brave souls have been spotted donning the coonskin cap while walking the streets of New York City’s SoHo and Williamsburg neighborhoods.

7. THE DEERSTALKER HAT

Not surprisingly, the deerstalker hat is worn for hunting. However, fictional detective Sherlock Holmes popularized the hat in the 19th century, trotting about in his novels clad in a cape and the smart headwear. Not surprisingly, the hat is most often worn by rural outdoorsmen—not by genteel city dwellers like Sherlock.

8. BOATER HATS

British sailors in the 19th century donned hard, flat-topped hats made from water-resistant varnished straw. Later, English sportsmen wore the stiff-brimmed hats while rowing along the Thames. The look caught on, and by the 1890s, everyone was wearing boater hats—even girls and women, who were becoming more active in outdoor sports.

Boater hats crossed the Atlantic, and were fashionable among middle-class men and college boys alike. During election campaigns, they were dressed up with red, white, and blue bands and transformed into political symbols.

9. THE PILLBOX HAT

The pillbox hat was a simple, elegant, and no-frills accessory hat that was popular from the 1930s through the late 1960s. The round, brim-less hats were worn perched on top of the head. True to their name, they were also shaped like a pillbox.

10. THE HENNIN

Those pointy medieval princess hats with veils have a name: They’re called hennins. Worn by European royalty, the tall, stiff hats were fashioned from expensive fabric and girded with wire or padding. In France, some hennins reached heights of up to three feet. However, English versions of the hennin were smaller and less dramatic.

11. THE FASCINATOR

Unless you’re running with a royal crowd, fascinators probably aren’t on your radar. But they should be: these decorative headpieces can be as simple or as elaborate as you’d like. All around the world—going way back to ancient times—women have dressed up their locks using feathers, cloth, flowers, and more, creating fascinator-like looks. Our favorite is probably the 13th century ramshorn, which involved a headband-brooch combo, plus two coiled buns reminiscent of a certain science fiction heroine.

12. THE BICORNE HAT

In the late 18th century, European and American military and naval officers (think Napoleon Bonaparte) wore bicornes. The hat had a broad, floppy brim, and its front and back section were folded over and pinned together. This feature made the accessory less cumbersome and easier to carry.

13. THE CALASH

The sky-high hairdos of the late 18th century demanded equally lofty protection. Massive bonnets called calashes fit the bill. Each had wood or whalebone sewn in for stability, but the super tall toppers were collapsible, too.

14. THE PHRYGIAN CAP

The Phrygian cap is most commonly associated with freed Roman slaves, who wore a variant of the soft, pointy hat to symbolize their independence. The hat was later adopted as a symbol of liberty during the French Revolution.

15. THE BALMORAL BONNET

This floppy, tasseled beret was named after Queen Victoria’s Scottish estate, Balmoral Castle. The traditional hat is worn tilted sideways, and is typically paired with Scottish highland dress.