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One thing that illustrated and photographic archives have taught us is that people have always known how to rock a stylish piece of headwear. From squat caps to towering toppers, history has produced a hat for every occasion. Here are 20 old styles that, with a healthy dose of fashion and confidence, could still look just as fabulous today.

1. THE CLOCHE

A woman wearing a cloche hat decorated with flowers.

Sasha, Getty Images

The sleek, head-hugging cloche was the perfect companion to the bobbed hairstyle worn by flappers in the 1920s. The hats were to emphasize their bell-shaped silhouette, though they also offered a blank canvas for embellishment. The cloche was most popular during the Jazz Age but it’s occasionally incorporated into retro fashion styles today.

2. THE OTTOMAN HEADDRESS

In Ottoman ceremonial costumes, hats played a starring role. The headgear often featured bright colors, feathery ornamentations, and elaborate designs that. The wearer’s class, religion, gender, and clan could all be gleaned from the way the fabric in their headdress was layered.

3. THE BOWLER HAT

Oscar Wilde wearing a bowler hat in 1885.

Oscar Wilde wearing a bowler hat in 1885.

Hulton Archive/Getty Images

The top hat was popular in the 19th century but it wasn't always the most practical choice for outdoor activities. When looking for a way to protect the heads of horseback riders from branches, brothers Thomas and William Bowler came up with their namesake cap. The bowler hat was sturdy, compact, and appropriate for most any occasion. Though the bowler hat largely fizzled out by the 1980s, the item's original London manufacturers Lock & Co. still.

4. THE PILLBOX HAT

Woman wearing a pillbox hat in the 1960s.

Chaloner Woods, Getty Images

Unlike some hats from history, this one was prized for its simplicity. It could be easily identified by its brimless, round shape evoking that of a pillbox. It began gaining steam in the 1930s before reaching peak popularity with First Lady in the 1960s.

5. THE FASCINATOR

Victoria Beckham wearing a fascinator in 2007.

Victoria Beckham wearing a fascinator in 2007.

Mark Mainz, Getty Images

Depending on the look you’re going for, a fascinator can be worn as a subtle accent item or a show-stealing statement piece. The hat is defined as an ornamental headpiece that’s secured to the crown using a headband or comb. Once they fit that criteria, fascinators can take the form of flowers, feathers, fabric, or whatever else the wearer can engineer to stay on their head. And though they're still popular in the U.K., Americans don't tend to utilize fascinators outside of.

6. THE TRI-CORNER HAT

A tri-cornered hat from Spain, circa 1780.

A tri-cornered hat from Spain, circa 1780.

Gabriel Bouys, AFP/Getty Images

In 17th century Europe and America, tri-cornered hats, or tricornes, gave men the opportunity to show off their lustrous wigs poking out from beneath the upturned brim. It's no surprise then that the hat style died out with the powdered wig fad, but that doesn't mean it isn't fit for a comeback. Even if wearers don't have wigs to flaunt, they could take a page from our forefathers' book and the hat itself with feathers, brocades, and fabrics—or maybe just insignias.

7. THE DEERSTALKER HAT

British actor Peter Cushing wearing a deerstalker hat circa 1960.

British actor Peter Cushing wearing a deerstalker hat circa 1960.

Keystone/Getty Images

If you’ve seen this hat anywhere, it was most likely on the head of someone portraying Sherlock Holmes. The headpiece has been tied to the character since the books were published in the 19th century (it was the illustrations—not the story—that did it, as in the text). It’s peculiar that an urban detective would be wearing a deerstalker hat in the first place, considering they were designed for hunting game and not tracking clues, but the smartly styled hat's comeback should be... elementary.

8. THE HENNIN

These striking hats were a clear sign of royalty in the medieval era. Reinforced with wire or padding and draped in fine fabric, the cone-shaped hennin is still synonymous with the stereotypical princess today. English hennins were fairly modest in height, but the French version reached up to to three feet and the hat's towered five to seven feet high.

9. THE NEWSBOY CAP

Newsboys in St. Louis in 1910.

Lewis Hine, // Public Domain

This hat goes by (the big apple, the eight panel, the Gatsby), but its strongest association is with newsboys at the turn of the 20th century. The floppy, brimmed cap hair coloring ideas for brunettes 2018 wasn't just popular with the younger working class. It was worn by men across the social ladder and was a common sight on the golf course.

10. THE PEACH BASKET HAT

Actress Marion Davies in a peach basket hat.

Actress Marion Davies in a peach basket hat.

// Public Domain

The origin of this hat name isn't too hard to figure out: It resembles a bulky, over-turned fruit basket. The peach basket hat first appeared at the start of the 20th century, but it was shunned by many for being an "" display of vanity during the first world war. It was revived in the 1930s and experienced a popularity streak until the 1950s.

11. THE PORK PIE HAT

Actor Buster Keaton wearing his signature pork pie hat in 1939.

Actor Buster Keaton wearing his signature pork pie hat in 1939.

// Public Domain

This hat is known for having a domed crown inside a pinched rim, creating a shape similar to that of a certain savory pastry. The style was in the 19th century and was later embraced by men’s fashion in the early 1900s (thanks in part to Buster Keaton). It’s not as popular as it was in the 1920s but it recently enjoyed a brief return to the spotlight by way of the Heisenberg character on Breaking Bad.

12. THE CARTWHEEL HAT

Actress Fanny Brice wearing a cartwheel hat circa 1910.

Actress Fanny Brice wearing a cartwheel hat circa 1910.

// Public Domain

Out of context, a cartwheel hat could be mistaken for an hor d'oeuvres platter or a tiny landing pad. The hat was worn slightly askew for an eye-catching look and was often crafted from luxurious materials. But after catching on in the 1930s, the broad hats have since fallen out of fashion.

13. THE CHAPEAU BRAS

With the, gentlemen in the 18th century proved you don't need to compromise style for convenience. The bicorne shape of the hat was designed to both sit comfortably on a head and fold flat when tucked beneath an arm. The French name roughly translates to "hat arm." It was a popular hat style among military men in the 1800s, including U.S. admiral George Dewey.

14. THE BOUDOIR CAP

Hat on mannequin.

For a brief period at the turn of the 19th century, hair nets were fashionable. Women used to protect their hair while getting dressed in the morning or at night, though more stylish designs also worked as statement-making loungewear. Typically made from silk, muslin, or other lingerie fabric, the cap was the perfect companion to the kimono negligee, which was just beginning to gain popularity in the West at the time.

15. THE EUGÉNIE HAT

The is named after Empress Eugénie de Montijo, one half of France’s last reigning royal couple. It’s traditionally made from felt or velvet and worn tilted forward slightly to cover the wearer's eye. The hat saw an initial popularity spike in the mid-19th century, then a second after Greta Garbo worse a version of it in the 1930 film Romance.

16. THE GAINSBOROUGH HAT

Gainsborough hats, or, were popularized by 18th-century artist Thomas Gainsborough, who often depicted the society women in his portraits beneath massive headwear. The hats are known for their wide brims and over-the-top embellishments. It wasn't uncommon to see women walking around with perched on their hats during the style's peak.

17. THE PAMELA BONNET

Named for the protagonist of Samuel Richardson's 1740, the was an elegant hat option for women in the 19th century. It's crafted from straw and tied with a ribbon in such a way that folds the wide brims against the wearer's cheeks. The sides of the hat slope down and away from the head, allowing the woman’s fashionable ringlets to peek out.

18. THE HALF HAT

The Queen wearing a half hat and waving from a car.

Queen Elizabeth II wearing a half hat in 1954.

The sleek, close hat trend reached its peak in the 1950s with the half hat. Part-hat, part-hair accessory, the half hat cups the back of the skull and curves across the crown, stopping just short of the ears. Milliner received an American Designer award for the hat in 1941.

19. THE WHOOPEE CAP

The whoopee cap is best known as the crown hat Jughead wears in the Archie comics. Instead of buying a professionally-made version from a hat shop, wearers fashioned caps of their own by tattering the brims of old and turning them inside-out. The style appeared recently on, the gritty Archie reboot, so a comeback may be on the way.

20. THE HOMBURG

British Foreign Secretary Sir Anthony Eden (right) with Neville Chamberlain, Leader of the Conservative Party, wearing Homburg hats while walking in London in 1937.

British Foreign Secretary Sir Anthony Eden (right) with Neville Chamberlain, Leader of the Conservative Party, wearing Homburg hats while walking in London in 1937.

Central Press/Hulton Archive/Getty Images

The isn't a household name like the top hat or the fedora, but the men’s hat is still a classic. The style is distinguished by a curled brim and a dent depressing the center of the crown. King Edward VII launched the trend in the late 19th century. When he brought a hat back with him following a visit to Bad Homburg, Germany, the rest of the world noticed his new look and started wearing Homburg hats of their own.

A shorter version of this story originally ran in 2017.



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