20 Old Hat Styles Due for a Comeback

John Firth, BIPs/Getty Images
John Firth, BIPs/Getty Images

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 typically left plain 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 signified status. 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 sell thousands each year.

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 Jackie Kennedy 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 Derby Day attire.

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 upgrade the hat itself with feathers, brocades, and fabrics—or maybe just sports 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 Sir Arthur Conan Doyle never mentions the cap 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

Illustration of a French woman wearing a hennin in the 15th century.
plaisanter, Flickr // CC BY-SA 2.0

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 Mongolian predecessor towered five to seven feet high.

9. THE NEWSBOY CAP

Newsboys in St. Louis in 1910.
Lewis Hine, Wikimedia Commons // Public Domain

This hat goes by many names (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 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.
Wikimedia Commons // 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 "unpatriotic" 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.
Wikimedia Commons // 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 originally worn by women 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.
Wikimedia Commons // 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

Bicorne hat.
Marie-Lan Nguyen, Wikimedia Commons // CC BY 2.5

With the chapeau bras, 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

For a brief period at the turn of the 19th century, hair nets were fashionable. Women used boudoir caps 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 Eugénie hat 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 picture hats, 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 stuffed birds perched on their hats during the style's peak.

17. THE PAMELA BONNET

Named for the protagonist of Samuel Richardson's 1740 novel, the Pamela bonnet 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 Lilly Daché 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 fedoras and turning them inside-out. The style appeared recently on Riverdale, 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 Homburg 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.

5 Fast Facts About Billy the Kid

On September 23, 1875, Billy the Kid was arrested for the first time. Whether you think he was a misunderstood old West hero or nothing but a cold-blooded killer, it's impossible to argue that he was an interesting man. Here are five facts to prove it.

1. HIS "REAL" NAME IS A TOPIC OF DEBATE.

Billy the Kid's real name? Henry McCarty. Or maybe William Bonney. Or Henry Antrim. Take your pick. He was born Henry McCarty, but there's some speculation that his dad may have been a man named William Bonney. Billy the Kid started using his name at some point in 1877. Antrim was his step-father's last name; he went by that for some time as well.

2. HE WORKED AT A CHEESE FACTORY.

Billy the Kid wasn't always engaging in illegal activities and shooting people; he once worked at a cheese factory—at least he did according to Charlie Bowdre, a man who would later be in Billy's posse, and was part owner of the cheese factory. Bowdre's descendants have said this is where the two of them met, although his employ was short.

3. HIS LEGEND MAY BE A BIT OF AN EXAGGERATION.

You may have heard the legend that Billy killed 21 people—one for each year of his rather short life. It's just that: legend. We only have evidence that Billy killed four people, two of them prison guards. He may have "participated" in the deaths of up to five more people.

4. CONTRARY TO POPULAR BELIEF, HE PROBABLY WASN'T LEFT-HANDED.

The reason this notion became widespread is because of the famous ferrotype of him that shows him wearing a gun belt with the holster on the left side. It was later discovered that the image has been reproduced incorrectly and flipped to show the mirror image of what really was. The picture actually shows Billy with his gun on his right hip.

5. SOME PEOPLE BELIEVE HE FAKED HIS OWN DEATH.

Many people—including some claiming to be Billy himself—have said Billy didn't actually die on July 14, 1881 in Fort Sumner, New Mexico, which is the official story. Many claim that Sheriff Pat Garrett didn't kill Billy, but actually helped him fake his death and happily ride off into the sunset. No evidence has ever been found to support this, though.

Men claiming to be Billy include Ollie "Brushy Bill" Roberts and a man named John Miller. Brushy Bill started claiming to be Billy the Kid in 1949, and knew quite a few intimate details about Billy's life and the Lincoln Country War. But there were several gunfights he was pretty clueless about, and photo comparisons using sophisticated computer programs show the men to have completely different bone structure and other features.

As for John Miller, his claims were basically put to rest in 2005 when his bones were disinterred and DNA samples were taken. They were compared to a blood sample thought to be Billy the Kid's and there was no match.

10 Intriguing Friends Fan Theories

Getty Images
Getty Images

Friends is a show about twentysomethings navigating life, love, and work in New York City. Ot at least that’s one theory about the beloved sitcom, which debuted on this day in 1994. Here’s another: Friends is a glimpse inside a mental ward, where six disturbed patients are working through their personality disorders. In the 14 years since it went off the air, Friends has inspired a ton of wild fan theories on Reddit and Twitter. Here are a few of the strangest (and be careful: Mr. Heckles’s murderer is still at large).

1. RACHEL DREAMED THE WHOLE THING.

In the summer of 2017, this photo of the Friends season four DVD box ignited a fan frenzy. The image on the box shows the titular pals snoozing side by side. Ross, Phoebe, Monica, Chandler, and Joey all have their eyes shut, but Rachel—resting right in the middle—is wide awake and looking directly at the camera. Why is she the only one with her eyes open? Some fans suggested Rachel was plotting something sinister, or secretly very “woke.” But plenty more insisted it was proof the whole show was Rachel’s dream. According to one Twitter fan, Rachel fell into an anxiety-fueled dream the night before her wedding to Barry and imagined her own group of hip New York friends to cope with her frustration and dread. Except she woke up to reality the next morning, as shown on the DVD cover, where she’s surrounded by her dream friends.

2. PHOEBE HALLUCINATED THE SHOW.

Another popular theory suggests the show was all in Phoebe’s head—only this take is much darker. The basic premise is that Phoebe never got off the streets. She was a lonely, homeless woman with a meth addiction who peered into the window of Central Perk one day. She noticed five friends laughing over coffee, and imagined herself as part of the gang. In this fantasy, her pals didn’t always get her weird sense of humor, but they loved her anyway. In reality, the twentysomethings in the window were wondering why that “crazy lady” was staring at them. This theory gained so much traction that a journalist asked Friends co-creator Marta Kauffman about it at a television festival. She quickly threw water on the whole thing. “That’s the saddest thing I’ve ever heard,” Kauffman replied. “That’s a terrible theory. That’s insane. Someone needs a life, that’s all I’m saying."

3. IT WAS ONE LONG PROMO FOR STARBUCKS.

The cast of 'Friends'
Warner Bros. Television/Getty Images

According to one manic Facebook rant, Friends was not a sitcom at all. It was actually a 10-year marketing ploy, designed to make Starbucks the new go-to destination for young people. Why else do the characters spend so much time in a coffee shop? True, the shop is not called Starbucks, but the subliminal evidence lies in Rachel’s last name (Green, like the Starbucks company color) and hair (styled like the mermaid in the Starbucks logo). Then there’s Ross and Monica’s last name, Geller, which is close to the German word gellen. It means “to yell,” just like the Starbucks baristas calling out customer names. The case only gets flimsier from there, but if you really want to read about how Chandler and Moby Dick are connected, you can dive down the rabbit hole here.

4. ROSS LOST CUSTODY OF BEN BECAUSE HE WAS A BAD DAD.

Ross’s son Ben arrives in the very first season of Friends, in the aptly titled episode “The One with the Birth.” He’s a constant character for several seasons, but as the show goes on, Ross seems to spend less and less time with his kid. Ben disappears after the eighth season, and never meets his half-sister Emma onscreen. There’s one explanation for this dropoff: Ross lost custody of his son due to increasingly disturbing behavior.

The blog What Would Bale Do lays out a bunch of examples: Ross sleeps with his students, tries to hook up with his cousin, and asks a self-defense instructor for help scaring his female friends. He’s also generally pretty jealous and possessive. According to this theory, Ross’s ex-wife Carol hit a breaking point and took full custody of their son, which is why Ben stops coming around his dad’s apartment in the later seasons.

5. MR. HECKLES WAS MURDERED.

Rachel and Monica’s mean old neighbor dies of natural causes in season two—or at least that’s what they want you to think. By one Redditor’s account, Mr. Heckles was killed in cold blood. Moments before he dies, Mr. Heckles shows up at Monica and Rachel’s door, complaining that their noise is disturbing his birds. (He does not have birds.) Monica says they’ll try to keep it down and as Mr. Heckles leaves, he says he’s going to rejoin his “dinner party.” Minutes later, he’s dead. Ergo, his dinner party guest killed him. Of course, the likelier explanation is that Mr. Heckles was a crazy old man who wasn’t even having a dinner party. But where’s the fun in that?

6. THERE’S A REASON THEY ALWAYS GOT THAT TABLE AT CENTRAL PERK.

The cast of 'Friends' chats with talk show host Conan O'Brien
Warner Bros. Television/Getty Images

How did the gang manage to snag the coveted center couch at Central Perk every single time? Simple: Gunther reserved it for them. It was all part of his ongoing campaign to win Rachel’s affections, and it explains why the group never had to fight for seating space. Well, except that one time.

7. THERE’S A PARKS & RECREATION CROSSOVER.

In “The One With All the Candy,” Rachel insists she doesn’t sleep with guys on the first date, only for her friends to immediately call her out. Monica rattles off three names: Matt Wire, Mark Lynn, and Ben Wyatt. Could she be talking about the same Ben Wyatt from Parks and Recreation? According to Reddit, their ages check out. Ben would’ve been 26 at the time of the episode, making him a perfectly acceptable one-night stand for 29-year-old Rachel. But how does Leslie Knope feel about this?

8. JUDY GELLER HAD AN AFFAIR THAT PRODUCED MONICA.

Ross and Monica’s mom doesn’t even try to hide her favoritism. Judy Geller thinks Ross is a genius and Monica is, well, trying. (But could be trying harder.) One bonkers and since-deleted fan theory suggests Judy’s preference stems from a family secret: At some point in her marriage to Jack Geller, she had an affair, one she could never forget because it spawned Monica. Judy’s shame over this tryst is what causes her to lash out at Monica and praise Ross, her one 'legitimate' child.

9. THEY’RE ALL IN A PSYCH WARD.

Courteney Cox, Jennifer Aniston, and Matthew Perry in a scene from 'Friends.'
Warner Bros. Television/Getty Images

What if Central Perk wasn’t a coffee shop at all, but rather the cafeteria at a mental institution? As one theory goes, all six main characters are suffering from personality disorders. They’re confined to a facility for treatment, and can only shuffle between their rooms (i.e. their “apartments”) and the cafeteria (i.e. “Central Perk”). This situation also explains why the group is so hostile toward new people. They’re not actually teasing Monica’s new boyfriend; they’re attacking anyone who tries to take one of the friends out of the mental hospital.

10. JOEY REALLY WANTED SOME PANCAKES.

This very silly—but very solid—fan theory is centered on Joey’s love of food. In “The One With Ross’s Library Book,” Joey has a one-night stand with a woman named Erin. He doesn’t want to see her again, and asks Rachel to break the news to her over pancakes. Apparently Chandler used to do this when he lived in the apartment. He’d even save extra pancakes for Joey. Rachel refuses to be a part of this, but once she’s left alone with Erin, she feels bad and offers to cook. Things escalate over the episode and pretty soon, Joey is the one who’s too clingy for Erin. Rachel has to tell him and, feeling bad yet again, she offers pancakes. Reddit claims this was all just a plot for pancakes. It kind of adds up: Joey can’t cook but likes to eat, and he has enough soap opera money to pay an actor (Erin) to play a part in this conspiracy. So he cons his roommate into making pancakes, twice, in a ruse that’s both delicious and diabolical.

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