Never Bareheaded

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"She doesn't 'just wear a hat'. She always wears a hat."

— Becky’s description of Dina, Dumbing of Age

A character always appears wearing a headdress of some kind, and never, ever takes it off. It doesn't have to be a hat, any kind of headgear is fine. Furthermore, it doesn't always have to be the same headgear, the point is that this character is never seen bare-headed. This gives him a certain mystique since while it might just be that he wears the hat because he feels like it, the fact remains that we never learn what his hatless head looks like.

Please note that this is not about characters who usually wear a hat. It's for characters who always and without exceptions wear one. Maybe exceptions can be made if the character is seen hatless just once, but no more than that, or if it happens very rarely and is made a big deal of. A good rule of thumb is that if it doesn't seem weird, when you think about it, that the character in question always wears headgear, then s/he doesn't qualify. So obviously a character that appears briefly in two episodes of a three-hundred-episode series doesn't qualify, even if his fedora was on all the time.

In some cultures, a hat is a mandatory article of clothing — something you would no more leave off than you would leave off wearing pants. This may be required for only one sex, or for both.

Often overlaps with Signature Headgear (for characters who are known for wearing headgear that makes them stand out) and Please Keep Your Hat On (for characters who really don't want to show off whatever is under the hat). Men with Baldness Angst also often employ this trope to hide their shame from the world. Sometimes overlaps with The Faceless. Contrast Helmets Are Hardly Heroic.

Examples:

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Anime & Manga

In Black Cat, the protagonist's partner, Sven Vollfied, never stops doing three things; wearing a hat, flirting, and smoking. At one point the hat gets ruined, but he's got a spare prepared.
In Bleach, Urahara Kisuke wears his green-and-white-striped hat constantly. The brim usually keeps his eyes in shadow, and Urahara frequently uses it to help obscure the rest of his face. When someone knocks his hat off, Urahara is quick to put it back on, even if it has been damaged.
In the erotic manga Bondage Fairies, creator Kondom's Author Avatar is always depicted wearing a giant condom as a full face hood (and two smaller condoms as gloves).
Chiriri from Bottle Fairy always wears a hat or head covering of some type.
Sayoko Shinozaki from Code Geass is never seen without her maid's headdress, even when in her ninja outfit on a mission.
Captain Tsubasa: Mostly applies during matches, but Genzo Wakayabashi is the only goalkeeper in the series who always and without fail wears a cap while playing. Only a few times it gets knocked off during rough plays and there's one instance he used it for a save.
Inspector Megure in Case Closed is always seen with his iconic hat. In Episode 218/File 286, it was revealed that he always kept his hat on so that nobody would see the scar on his head which he received many years ago in a case which involved his would-be wife.
Karasawa from Daily Lives of High School Boys, who is always wearing a baseball cap.
One of the theater troupe members in Dance Till Tomorrow always wears a huge frog mask.
Doraemon:
- Haruo, one of Those Two Guys alongside Yasuo from Nobita's class, is never seen without his baseball cap.
- The Conductor of the titular Super-Express from Doraemon: Nobita and the Galaxy Super-express always had his Conductor's Hat on at all times, even when he's clinging atop the express during a high-speed chase and getting thrown off his feet when the express crashes on two different deserted planets.
- Pibu and Poppi from Doraemon: Nobita and the Spiral City, a pair of andromorphic toy pigs can be differentiated from the other pig residents from their permanent headgear, the former wearing a cap and the latter a pink bow.
- Bulkin the merdemon lord from Doraemon: Nobita's Great Battle of the Mermaid King wears a face-obscuring helmet on him at all times that shouts "EVIL!" whenever he's onscreen, and the audience never sees how his true face actually looks like. His anime-exclusive dragon Tragis also have a horned helmet he's never seen without.
- Subverted with Luca from Doraemon: Nobita's Chronicles of the Moon Exploration, a New Transfer Student in Nobita's class who wears his cap everywhere he goes (lampshaded when Gian and Suneo calls him "that new kid with a cap") - because he's actually a Human Alien with rabbit ears, revealing his identity to Doraemon and gang after befriending them by removing his cap. Luca never wears his cap after the reveal halfway through, and it seems like he gave Nobita his cap as a memento before leaving earth (his cap can be seen in Nobita's bedroom in the next movie, Doraemon: Nobita's New Dinosaur, as a Continuity Nod).
Fujita from Dorohedoro never takes off his hat. It's the kind of hat that that guy in Fargo wore.
JoJo's Bizarre Adventure:
- Jotaro Kujo's hat is such an integral part of his character that it seems to merge with his hair. And of course, he never intentionally takes it off, but it does get knocked off his head once or twice by enemies.
  Jotaro: You knocked off my hat. I don't even take that thing off when I'm underwater.
- Guido Mista from Golden Wind is never seen without a hat, whether it be his coif-like hat he wears in the present or the beanie he wears in flashbacks.
- D an G from Stone Ocean is always seen wearing a Pickelhaube, which is especially odd given he's a prisoner being held in a maximum-security ward. His helmet is such a key part of him that his Stand appears to be wearing one as well, and it stays on even when F.F. decapitates him from within. The same part has Ungalo, who's never seen without his purple knit cap, though it was slightly dislodged when he was shot at in his introduction.
- Josuke Higashikata, the JoJo of JoJolion has literally never been seen without his 'dixie cup' sailor hat. He's even found wearing it when he's pulled out of the Wall Eyes otherwise naked.
You could probably count the number of times that Chika Fujiwara from Kaguya-sama: Love Is War is shown without her bow on one hand. She even keeps it on when she's wearing a bald cap or when she has a towel wrapped around her head after getting out of the bath.
In Kobato., Kobato herself is never seen in public without some kind of hat. This turns out to be justified, since her hats hide a spiritual crown which indicates that she's actually dead.
Jigen, from the Lupin III franchise, is never seen without his fedora. Unless he's in disguise. It's actually been stated that he's such a good shot simply because he always wears it. He aims along the brim.
In One Piece we have several examples:
- Chopper, who always wears his pink hat (later a blue helmet on top of the pink hat).
- Usopp, who always has some kind of headgear on, his most iconic being the olive net-patterned cap.
- Brook and his top hat, which he switches for a weird crown-shaped hat after the timeskip.
- Surprisingly averted with the main character, Luffy, the only character (aside from Chopper) whose hat is actually important. His straw hat is his symbol, going so far that when he achieves fame, the World Government calls him "Straw Hat" Luffy, and his crew the "Straw Hat Pirates". It's Luffy's most precious treasure, given to him by his idol. And, as it turns out, it was once the hat of Gol D. Roger, the pirate king. And yet, he's constantly seen without it, typically taking it off at the start of major fights and either setting it on the ground or giving it to a crewmate. Other times he wears the string of the straw hat around his neck instead of on his head.
- Killer, one of the Eleven Supernovas, never takes his helmet off, not even to eat. As a result, his favorite food tends to be what he can fit through the holes in his helmet, especially pasta.
Pokémon:
- Ash from Pokémon: The Series always has his trademark baseball cap on. The number of times he's seen without it is directly proportional to the number of formal outfits he's been put into over the course of the show. He's also occasionally seen without it when he's asleep.
- Red from Pokémon Adventures has had his hat off in only one chapter.
In Samurai Deeper Kyo, Benitora always wears a bandanna.
From Sgt. Frog, all Keronians have hats, usually a long-eared one with their personal symbol on it. One episode involved a notorious un-reveal when Keroro switches to a baseball cap after his hat is picked up by a toddler.
Spy X Family: Anya has two little 'horns' on her head, which she never takes off even when sleeping. For a Fashion-Shop Fashion Show sequence, she either switched them for an equivalent that matched the outfit or wore a hat. The only time she's been seen without any headgear is a flashback to the lab where she gained her telepathic powers, where she had Odango Hair.
The title character of Squid Girl, who would die if she removed her hat. It's hinted that her "hat" is actually her scalp (which explains why removing it is lethal); in one issue where she was suffering from amnesia, she tried to remove it only to find it fused to her head.
The titular Princess of 'Tis Time for "Torture," Princess is constantly wearing something on her head. Usually it's her Requisite Royal Regalia crown, but she occasionally switches it out for such things as a bike helmet.

Asian Animation

BoBoiBoy: The titular Kid Hero always wears his iconic orange "dinosaur" cap. One of many comic strips from the earliest magazines for the show that lampshade this involve his grandfather being shocked when BoBoiBoy casually states that he hasn't washed his hat in two months. BoBoiBoy: The Movie shows that even in the bathroom, he wears a shower cap which is similar to his hat. In the movie's climax, his full head of hair is seen for the first time after Bora Ra knocks it off of him, revealing BoBoiBoy's black hair to have a frontal skunk stripe.

Comic Books

Jughead Jones from Archie Comics is seldom seen without his signature crown-shaped hat.
The title character of obscure Swedish comic book Bobo always wore a Tyrolean hat.
The title main character from the British comic Buster (who was originally said to be Andy Capp's son) was never seen hatless except for the final issue. Apparently, he looks just like Dennis the Menace (UK) under it.
Doctor Doom is about as likely to be seen without his helmet as he is to show up with a can of Budweiser and playing the kazoo. Occasionally he'll take the mask off, almost invariably when facing away from the reader. This is because, most of the time, he's horribly scarred underneath - either from the explosion that initially scarred him or from putting on the helmet without letting it cool first - and his vanity won't permit him to go bareheaded and put that on display.
In the Swedish comic Herman Hedning, Herman always wears a helmet.
Judge Dredd almost never takes his helmet off. When he does, his head is always obscured by something else. The one exception to this was one time when he'd had his face changed into a completely different one.
- An early story did intend him to remove his helmet on-screen and reveal his face, to cow some perps he was dealing with at the time - but the illustrator Massimo Belardinelli could not make it intimidating enough, so they opted to instead censor it and imply a Nightmare Face. From here on it grew into a Running Gag, and from there into a symbol: John Wagner has come to declare that it symbolizes the facelessness of justice, and that it'd be unnecessary and downright harmful to ever see his true face.
- One story had an artist going blind, wishing to make her final work about Dredd's face. Dredd refused on the above grounds: justice is meant to be faceless. He did let her feel him after she'd finally gone blind, however.
- Another story goes as far as to suggest this tendency as a "deeply embedded personal neurosis": the monkey vigilante Chimpsky employed it to good effect to flee from him.
Cougar from The Losers keeps his hat on.
Some runs of The Mighty Thor have depicted Loki this way, though as with many comic book characters it's Depending on the Artist (it's fairly established that his hair is short — shorter than in the film version, black, and pomaded back). The J. Michael Straczynski/Kieron Gillen era took this trope to heart, however, by depicting a Loki who wore his horned helmet and cowl even when shirtless and hammering at a sword à la The Blacksmith. Current/Teen!Loki averts the trope, he pretty much only wears a circlet thingy, and even that only on missions however his (possible) evil, future self was shown to wear the classic helmet.
Jeremiah from Monica's Gang is always seen wearing a red hat, since his first appearance in the comics.
The Phantom Stranger: It is extremely rare for the Stranger to be seen without his trademark fedora and, even then, it is usually for no more a panel. The Madame Xanadu series shows that the Stranger has always worn some type of head covering, with the style changing through the eras: a hooded cloak in Camelot, a top hat in Victorian England, etc.
Molly Hayes from Runaways is almost always wearing some sort of animal-themed hat. She is also said to like some of the superheroes' various hats and helmets (such as Black Panther).
The Smurfs: Every single Smurf wears a white hat, except for Papa Smurf, who has a red one. They are rarely shown without a hat on, with Papa Smurf in the comic book story "The Black Smurfs" (and its English adaptation "The Purple Smurfs") having his hat blown off his head when his laboratory exploded after being turned into a Black Smurf, revealing a bald head. In both The Smurfs cartoon show and the film version of The Smurfs and the Magic Flute, there were some instances where the younger male Smurfs took off their hats to reveal bald heads underneath.
V from V for Vendetta is never without his signature Guy Fawkes mask.
Wonder Woman:
- Wonder Woman (1942): Lord Uvo and his Uranians never remove their helmet-hat combination headgear, and the only locals on Uranus shown without a head covering are slaves.
- Wonder Woman (1987): The Sangtee Empire has hats as a cultural thing, and the only time any kreel are seen without a hat or helmet on is when they're imprisoned and being tortured. Hats and other headgear are very important and the design seems to denote different positions of different kreel within the Empire.

Comic Strips

Andy Capp keeps his on. Lampshaded in one strip, where a constable delivers the cap to Flo. Flo's reaction suggests that Andy hasn't been out of the house ever since he lost it. In another strip, someone laughs at Andy for carrying an umbrella. Andy's response is that he's not going to sleep in a wet cap.
The title character from Barnaby has a fairy godfather named Mr. O'Malley, who never ever takes off his hat.
Beetle Bailey always wears either a hat or a helmet. In the Early-Installment Weirdness when Beetle hadn't joined the Army yet, he wore a fedora-like hat.
For many years in Doonesbury^note34 years to be exact, B.D. was never seen without some sort of helmet. He wore a football helmet at college, during his service in Vietnam, as a coach and as a pro football player, a soldier's helmet during both Gulf Wars, a policeman's helmet when he was a cop, and even riot gear at one point. However, this quirk disappeared when, on April 21, 2004, he lost a leg while serving in Iraq. His only reflections on losing the helmet was on July 31, 2004, when he asked himself "what was up" with his helmet obsession, and when he later reveals during a therapy session that his mother was very neurotic about safety, and made him wear protective helmets throughout his childhood, which resulted in him feeling naked without one as an adult.
Swedish comic strip Elvis used to feature a character called Totte, who always wore a beret.
Peter Fox from FoxTrot is never without his trademark baseball cap unless he is wearing some other kind of headgear, such as a football helmet. He even sleeps in it. In one strip it blows off his head and he subjects himself to a Humiliation Conga in order to get it back. The only two arcs that involved him being bareheaded for any length of time was one where he lost a bet and had to shave his head, and another where he was getting a haircut from a swimsuit model training to be a hairdresser.
Harry Dinkle of Funky Winkerbean never took off his band cap, except when wearing a helmet when helping with the school's construction. It wasn't until he retired from being the band conductor that he took it off... and his eyes were seen.
Hägar the Horrible even sleeps wearing his helmet. So does Helga, and pretty much everyone else in the strip who wears one.
Dean from Liberty Meadows is never seen without his backwards baseball cap. He even swims in it.
Barney Google, the original protagonist and still one of the title characters of Snuffy Smith always wears a hat. It was a top hat in the early days, but in more recent appearances he's leaned toward derbies.

Films — Animation

Arlo the Alligator Boy: Alia always wears her hood up, obscuring her ears and upper hair tuft. This extends to the series when she even puts on a hat over her hood and wears a hoodied wetsuit for swimming.
Food Fight: Dex Dogtective is always wearing his fedora, and it is played with in The Stinger when Sunshine Goodness removes it to reveal... another hat.
Frosty the Snowman never takes off his iconic magician’s hat. Justified, since the hat is what gave him life to being with, thus if he were to take it off, he would revert back to being an ordinary, lifeless snowman.
My Little Pony:
- My Little Pony: Equestria Girls – Friendship Games: Lemon Zest of the Crystal Prep Shadowbolts always wears headphones.
- My Little Pony: A New Generation: Queen Haven never takes off her crown, and sleeps, showers, and even swims with it. This greatly complicates matters for the heroes, as the Pegasus Crystal is the centerpiece of that crown and they need it to return magic to Equestria.
In Turning Red, Miriam is never seen without her green toque, even during gym class.

Films — Live-Action

The 1976 movie adaptation of Carrie has the character Norma perpetually wearing a red hat. When she gets her hair done, the device she's using wears it instead.
Charlie Chaplin almost never went without his iconic hat. The Immigrant goes as far as to show a scene of him repeatedly being asked to remove his hat at a restaurant, until the waiter gets fed up and snatches it off his head. As soon as it's on the table again, he puts it back on without any mind.
Dredd: Unlike the Sylvester Stallone version, Karl Urban's Judge Dredd is never seen without his helmet (except for a brief view of the back of his head while he is suiting up). Urban actually insisted on this, as Dredd in the comics never takes off his helmet.
In the Fat Albert movie, Dumb Donald explains that he always wears his hat because the animators didn't give him a face. He is forced to remove his hat and discovers that he indeed has a face. When Albert's friends return from the real world, Donald had to put his hat back on because, in their fictional world, he indeed has no face (just two eyeballs and a mouth floating around his head). Also apparently, Fat Albert himself is never bare-chested as when the clerk at the mall offers to help him take his sweater off to try on the new clothes.
Fat Albert: Uh... I can't take my sweater off 'cause... I don't know what's underneath it.
Gentlemen Explorers: The Magician is never seen without his grey top hat: even when the only other thing he is wearing his red long johns.
"Little Edie" Beale in Grey Gardens wears scarves and other head covers throughout the documentary, having lost all her hair to alopecia.
In the martial arts film, The Mighty One, the hero known as Water Knight is almost never seen without his eye-obscuring conical straw hat. It got knocked off his head during one battle, but he retrieves it and puts it back on moments later. In the final battle, he does remove his hat in order to throw it into an enemy's gut with enough force to fatally penetrate his victim.
Some Came Running: Bama Dillert always wears his hat. He sleeps with his hat. A violent fight breaks out when another gambler knocks Bama's hat off his head.
Star Wars:
- Darth Vader always wears his helmet, since it's part of his life support system. Seen only twice without it: the first time in a special pressure chamber, the second time dying. Though he is able go without it near the end in The Force Unleashed.
- The Tusken Raiders are never shown without their creepy masks and rags, as in their culture to expose any part of the flesh was forbidden and seen as a disgrace. However in Star Wars Legends it's suggested in Knights of the Old Republic that they may share a common ancestor with humanity, while in Jedi Knight: Dark Forces II a group of partially-masked Tuskens living offworld are shown to be vaguely feline, with flat faces and drooping jowls.
In Tampopo, Goro always wears his cowboy hat, even in the bathtub. The only times he takes it off are when he's letting Tabo wear it while he eats breakfast, and when it falls off when he's fighting Pisken.
Touch of Evil: Hank Quinlan is never seen without his fedora, indoors or out. It doesn't even fall off when he gets shot and collapses backward into a river.

Literature

While wizards on the Discworld may believe that a wizard is naked without his hat (and, conversely, isn't naked if he is wearing it), they have been known to remove them. Rincewind, on the other hand always wears his hat, and if he's somehow separated from it his immediate priority is to make a new one. After all, his Inept Magery is such that having a hat is basically the only thing that makes him a wizard.
In Eli's List, Eli always wears a Botafoga snowcap while she's awake and a nightcap when she's sleeping.
The gnomes of Gnomes have personal caps that they keep for life, sort of like the wands of Harry Potter wizards, and they never take them off except to sleep. A gnome would "rather be without his pants than without his cap," says the book. In one story, a misbehaving gnome's hat is held hostage until he changes his ways — of course he can't just go get another one.
Goblin Slayer: The titular character is almost never seen without his iconic one-horned helmet on. In the manga and anime adaptations, during the rare moments he takes his helmet off, his face is never shown.
Speaking of Harry Potter, Professor Quirrel (after the first time we see him) is never seen without his turban in the first book. There are rumors that he keeps garlic inside it to ward off vampires. In the climax, it is revealed that Lord Voldemort is possessing him and his face protrudes out the back of Quirell's head.
Referenced in a poem by Spike Milligan:
American detectives
Never remove their hats
While investigating murders
In other people's flats.

PS Chinese 'tecs
Are much more dreaded
And they always appear
Bare-headed!
In The Vampire Files, gangster Whitey Kroun got his nickname because he always wore a white hat, even as a teenager.

Live-Action TV

Frank Rossitano, he of the slogan trucker caps on 30 Rock.
Skinny Pete from Breaking Bad is never seen without his beanie. In El Camino, however, he gives his hat to Jesse as a parting gift before he goes on the lam.
In Brides of Christ, Sister Agnes's hair is always hidden under her habit. When the habits are changed to some which are more revealing, her grey hair shows, and she is mocked by the pupils.
Not a hat, exactly, but in El Chavo del ocho, a set of hair curlers is part of Doña Florinda's standard costume. No matter what time of day it is, or what's going on in the neighborhood, she always wears those curlers. More straight, Chavo and Quico are always seen with their hats. (Don Ramón has a hat, too, but he tends to throw it to the ground whenever he's angry.)
On Corner Gas, both Oscar and Hank always wear hats (Oscar's green hat being considered his signature item by other characters). Hank has spent a couple of episodes hatless for various reasons (trying to change his personality from a Virgo to a Libra, or having a good hair day for the first time in over 20 years), but Oscar's hat is a near-permanent fixture (Emma makes him take it off at the dinner table, and he doesn't wear it to bed or in the shower).
Charlie on Disneys One Saturday Morning is never seen without one. Though you could always see her blonde locks.
Dog with a Blog: Avery's friend Lindsey has a habit of always wearing a hat, even in inappropriate moments. The one time she realized she was bareheaded, she flipped out and had to stuff her head in her locker.
Game of Thrones: Lady Olenna Tyrell is always seen wearing a hat and veil color-coordinated to match her outfit. They're usually in the Tyrell house colors of teal and gold but she occasionally dons a black version as mourning attire.
Home Improvement: Most of the time, Wilson is wearing a floppy brimmed fisherman's hat, so only his nose and eyes are visible between the fence and the hat brim. Any time he is not wearing the hat, he has something else on his head, like a knight's helmet.
On one episode of Judge Judy, Judy orders a plaintiff to remove her large hat. The woman refuses, so Judy dismisses her case, probably figuring that if she can't follow such a simple request, she would probably be impossible to deal with.
All of the gnomes that are seen in Studio100's Kabouter Plop series are never seen without their hats. Even when they are sleeping they are still wearing their hats.
Tenkaichi from Lessons for a Perfect Detective Story never takes his hat off, even when he's in the bath. One character attempts to take it off him when he's asleep but he wakes up and stops them the moment his hat is touched.
Grandad Trotter was never seen without his trilby in Only Fools and Horses. It was such a piece of Signature Headgear that Delboy thought he put it in Grandad's grave at his funeral.
In The Mandalorian, members of the Mandalorian order the Children of the Watch are forbidden from showing their faces to other living beings, and are never seen outside of their very cool armour, helmet and all. Averted for Mandalorians from other orders, and occasionally the protagonist as well. The first two instances occur after either he or his adopted child ends up in a life-threatening emergency, but someone else helps him exploit a loophole in the creed. The third occurs before the child resumes Jedi training, when he silently asks to see his father's face before they part ways.
MythBusters: Unless he has a very good practical reason not to wear it, you're not very likely to see Jamie Hyneman without his beret. To the point that when a particularly fierce wind actually does blow it off, Adam is left slightly stupefied because something like that had never happened before.
Over the course of three seasons of Robin Hood, you could count the number of times that Much takes off his hat on one hand. It's actually a Tear Jerker when Robin takes off his hat for him in the very last episode. (It Makes Sense in Context).
In The Secret World of Alex Mack, Alex kept her hat on. They even did a song about it!
Guinan is never seen without a ridiculously large hat on Star Trek: The Next Generation, even in the wild west! Whoopi finally removed her hat in the TNG film Generations, as an act of symbolism for revealing her past.
Nisu Uuno from Wremja always wears a ski cap and refuses to take it off.
Japanese food and drinks journalist Rui Yoshida always dresses in trademark black and grey replete with flat cap.

Music

"God wants you to wear a hat" by The Whitest Kids U' Know.
The Taiwanese singer, Feng Fei-fei, always, always wears a cap, hat, or any form of headgear during concert performances, interviews and social galas, to the point where her fans would affectionally call her the "Queen of Hats". Even her Google Doodle depicts her in a series of assorted headgears!

Puppet Shows

Mr. Knack from Eureeka's Castle is almost never seen without his aviator hat, and if he's not wearing that, he'll have something else covering the top of his head.
The Swedish Chef of The Muppets is rarely seen without his chef's hat, even when wearing non-cooking clothes like a tuxedo. While most Muppet action figures released by Palisades Toys that had removable hats were packaged with the hat off, all Swedish Chef figures wore the hat in the packaging (a requirement from The Jim Henson Company, who wouldn't allow the figure to have a removable hat if he didn't wear it in the packaging). One of the rare times The Swedish Chef was shown without his hat was in a sketch where he made some spicy sauce. After tasting it, the sauce was so spicy it caused his hat to fly off his head. His bare head is only shown for a second before the chef looks up and then faints. On The Muppets (2015), The Swedish Chef was often shown hatless when outside of the workplace, though. He's seen hatless for most of his scenes in the episode "Pig Out".
On Sesame Street, Biff and Sully were rarely seen without their hardhats. Biff in particular has worn it at times when it would make sense not to, including a sketch where he plays a caveman, when in the bathtub in the "Do De Rubber Duck" number, and in an episode where Biff celebrates his birthday, he wears his hardhat underneath a party hat. Biff and Sully were both shown hatless in the number "We Coulda", where they imagine themselves having different jobs. Additionally, in the Sony/Loew's theater policy trailer "Don't Forget to Watch the Movie", Biff's hat falls off when he drills in the theater.

Theater

Fiddler on the Roof: "For instance — we always keep our heads covered, and always wear little prayer shawls. This shows our constant devotion to God. You may ask, "How did this tradition get started?" I'll tell you! ... I don't know. But it is a tradition!" Later in the play, Tevye jokes that maybe the reason Jews always wear hats is that they're always being forced out of their homes and forced to move someplace else.

Video Games

Desmond from Bloody Zombies is never seen without his British-style flat cap, even in his death scenes where zombies maul him apart.
Marumaro in Blue Dragon always wears a hat, which almost results in an Accidental Marriage in Kelaso Village.
Brain Dead 13: Lance almost always wear a baseball cap. The exception are Vivi's Salon, when Vivi takes it off and uses it as a gag to ensure that he can't scream during the painful "makeover", and some death scenes.
Club Penguin: Rookie is never seen without his propellor cap. He mentioned in a newspaper once that he has it glued to his head.
Masaru Daimon from the Danganronpa Another Episode: Ultra Despair Girls always wears earphones.
Daze Before Christmas have you playing as a Badass Santa out to save Christmas; while battling enemies your Santa hat stays on no matter how much jumping and kicking ass you pull off. Possibly justified because Christmas magic (you can even take cover from enemy attacks by hiding inside your hat).
F-Zero: Captain Falcon is only depicted without his face-obscuring helmet twice, if you win the GP in Master Class in F-Zero X and at the end of F-Zero GX's story mode. Even then, in the case of the latter, he faces away from the camera so you only see the back of his head. This is why it was a huge deal when, during his Heroic Sacrifice in the anime, his helmet flies off and his face is revealed. Other characters throughout GP Legend's run were able to deduce his Secret Identity and Falcon did outright reveal himself to one character, but his back was to the viewers then. Maybe that's because he was based on Judge Dredd.
Granblue Fantasy: Whether it's her royal regalia or her commoner disguise, Pholia always seems to have something on her head. This leads to the bizarre effect of her being an Erune as common knowledge in-universe and her bragging about the fluffiness of her ears to others despite the fact that players can't see them. Hiding her ears was probably done to prevent players from realizing that she's related to the Golden Knight before the story confirmed it.
Guilty Gear: After the first game, the mad Doctor Baldhead undergoes a Heel–Face Turn and from then on takes the name Faust and uses a brown paper bag over his head at all times, with the exception of his taunt in Guilty Gear Xrd where he shows his face to his opponent. Though in that case it is purposely hidden in shadow.
Heidelberg 1693 have you playing as a French musketeer caught in a Zombie Apocalypse and fighting undead monsters left and right, with your feathered musketeer hat staying on your head no matter what happens. Even if you're being ripped to shreds by monsters.
Inazuma Eleven: Several characers such as Max, Hiyori, and Touko wear a hat all the time, including when playing football or going to school. Nobody bats an eye. Max also has a special hat for sleeptime.
Kirby:
- King Dedede is always seen with a hat on, even while in a bathtub in Kirby: Right Back at Ya!. Usually he's wearing his classic beanie, but a few official illustrations show him with other hats.
- Magolor from Kirby's Return to Dream Land is never seen without his hood up; some of his special dialogue when you try to annoy him implies he has hair, but we never get to see it. Not even his One-Winged Angel forms avert this, since he wears the Master Crown to achieve those forms. The most we see of his head is during the Magolor Epilogue from the Deluxe remake of Return to Dream Land, where his hood is partially torn to expose one of his cat-like ears.
Downplayed in The Legend of Tian-ding. Your titular character wears a cap outdoors that stays on even when he's blasted by rockets, falling down pits or swinging through buildings, but there are two cutscenes where you remove your hat.
Snips in The Legendary Starfy would qualify, but who knows if that pink thing on her head is even a hat?
This was enforced with Link in The Legend of Zelda for a period. According to an interview, Nintendo gave the mangaka of the The Legend of Zelda: Ocarina of Time manga trouble because they had one scene where Link's hat is off. This has since been stopped, as Link is depicted hatless in games such as The Legend of Zelda: Breath of the Wild.
In contrast to his predecessor, who frequently removes his helmet to reveal a head of synthetic hair, Mega Man X is never shown removing his own helmet, if indeed he even can. Zero is similarly always helmetted (even after a change of body), though his own hair is visible anyway.
Onmyōji: Seimei is always wearing some sort of hat in all of his skins.
The trope is lampshaded in a scene that plays in the second PaRappa the Rapper game if you do badly at Hairdresser Octopus's stage, in regards to PaRappa himself, who is never seen not wearing his signature beanie:
Hairdresser Octopus: Hey! Take that stupid hat off! What does it look like in there?
PaRappa: Uh...I'm not sure myself.
In every main series installment up until Pokémon Sun and Moon, you were unable to remove the protagonist's hat. Particularly egregious was Pokémon X and Y, which introduced the ability for players to dress their characters in a variety of clothing, but still forced them to wear a hat of some sort.
Professor Layton. Though he does actually take it off briefly in the ending cutscene of Professor Layton and the Lost Future. Even in flashbacks before getting his famous top hat, he wears a cap. Averted in the Flashback sequences of Professor Layton and the Miracle Mask, where his younger self has a massive and unruly mop of hair. Which might be why he wears a hat all the time. Similarly, his apprentice Luke is always wearing a blue paperboy hat.
Lampshaded in Raidou Kuzunoha vs. The Soulless Army when Raidou beats up yakuza in a public bathhouse, naked but with his uniform cap on.
Charmy Bee in the Sonic the Hedgehog series is never seen without his pilot helmet on his head. Similarly, Vector never removes his headphones off his head.
Super Mario Bros.:
- According to Super Mario 64 and Super Mario Sunshine, bad things would happen to Mario in the event he ever removed his cap. In the former's case, Mario takes extra damage without it on. In the latter, the island's intense sun and heat cause Mario to slowly take damage from it unless he either gets under some shade or retrieves his cap, and in Super Mario 3D Land his small form lacks the cap. In future games, he can finally be seen without his iconic hat, but he still wears some kind of headgear, unless it's an Easter Egg.
- Almost all characters in Super Mario Odyssey wear some sort of headgear, be it hats, construction helmets, or others. On top of fitting with the game's theme of hats, this is important to gameplay: if you see an NPC who doesn't wear any headgear, this usually means you can capture them.
Seven of the nine classes in Team Fortress 2 wear some kind of headwear by default. Scout, Engineer, and Sniper can be made hatless by obtaining hat-free items equippable in the headwear slot. However, the Soldier can only have his hat replaced by other hats while the Spy, Pyro, and Demoman wear hats over their balaclavas, gas masks, and knit cap instead of replacing them—their models don't even include that part of their head (or, in the Pyro's case, any of his head) under it. Although for Demoman, one of them is an afro, which is supposed to be his actual hair, so it has a headband to cover the part of his cap's model that sticks out under it. There's a reason it's called Hat Fortress. It is possible for some of the characters to not wear a hat. By wearing a No-Hat Hat. So it isn't a hat by properties of not giving a hat, but it is a hat, and it goes in the hat slot ....
It would be a lot shorter to list the Touhou Project characters to which this doesn't apply, although in many cases the hair accessory is just a ribbon or a headband. Fanon has taken this concept and run with it—it's often joked that removing a Touhou's hat will kill them instantly. It's just that most things happen outside and there's a fairly small number of characters that consistently recur, so most characters are never seen bare-headed.
In Wizard101, even your default clothes include a hat.
Xenoblade Chronicles 2: Over the course of the game, Morag removes her hat a grand total of twice.

Visual Novels

Tamie Nogi in Princess Evangile, no matter what the situation, is never seen without something on her head, whether its her signature cat hat, swimming goggles, or a headband with a prominent ribbon. Subverted in her route, however, where there are two scenes of her without any headwear whatsoever.

Web Animation

Happy Tree Friends: Shifty always wears his fedora to differentiate himself from his brother, Lifty.
- Handy always wears his hard hat, on and off the clock.
The llamas in Llamas with Hats, appropriately enough.
The entire cast of Red vs. Blue is never seen without their helmets. In seasons nine and ten, most members of Project Freelancer are seen helmetless in flashbacks, but the guys from Blood Gultch still never take theirs off. It's also strongly implied that they almost never take the rest of their armour off either.
The Custodes of If the Emperor Had a Text-to-Speech Device never take off their helmets, despite having forgone the rest of their armor (and sanity) long ago.

Webcomics

8-Bit Theater: Black Mage's hat, which also obscures his face in shadow (except for his eyes). That's a good thing since there's apparently something just plain wrong with his face. He takes the hat off just once in the entire comic's run (though we don't see his face, and the poor sap who does get a look (Onion Kid) is driven insane by the sight).
Mr. Mighty of Everyday Heroes always keeps his mask on, even when relaxing at home.
In Girl Genius, the Jägermonsters are almost never seen without a hat. In fact, hats are seen as objects of reverence, and a Jäger without a hat is hardly a Jäger at all.
Girls of the Wild's:
- Choi Dal Dal never takes off her cat ears no matter what. They are detachable head accessories, though, as shown early in the comic as extra info.
- Lee Mi Nam is also never seen without his trademark cap.
Jameson from Girls with Slingshots always wears a bandana. This is Discussed by the girls when they realize they have never seen him without it. They learn that he wears it in bed and even has a spare for laundry day. They curiously encourage him to take it off, but he refuses. They stealthily untie it: underneath is another bandana. But when Jamie finally grabs that and pulls it away, Jameson is angry. It was covering something he wanted to hide: he is almost completely bald.
In El Goonish Shive, Duck, a comic-book shop regular, is never seen without his baseball cap which acts as an Eye-Obscuring Hat.
In Homestuck:
- Dad always looks dapper in his distinctive and dignified hat.
- Bro Strider is never without his cap.
Dina of It's Walky! is never seen without her trademark safari hat, even when sleeping or suspended upside down. In the entire series, she takes it off exactly once: when she is about to die.
- Her counterpart in Dumbing of Age wears a dinosaur hat constantly. This ends up becoming a thing with her girlfriend Becky, who would love nothing more than to see her bareheaded and tried convoluted schemes to do so. When she just asks, Dina claims that she vowed never to be bareheaded until she married, before revealing that was a joke and briefly takes it off. Dina later explains she feels anxious and insecure if something isn't around her head.
Kevin & Kell:
- Rudy wore his cap even when hired by a theme park to live as a wild animal; i.e., naked.
- Coney kept her bonnet on. In fact, the first time we ever saw her without it (after which she never wore it again) was many years into the comic. Rudy and Lindesfarne must not have seen her without it before either, because they were surprised by her Cousin Itt hair underneath.
xkcd:
- The only time Black Hat Guy was bareheaded was when his hat was stolen (for about two strips).
- White Hat Guy wears a white hat. Always.
- Beret guy implies that his hat is stapled on his head.
The main character of You Damn Kid! always wears his red cap, even while showering. In the sequel series, his son does the same.

Web Original

Atop the Fourth Wall: Linkara almost never takes off his hat. His theme song even establishes that he "Wears a purdy hat".
Producer of Honest Trailers Dan Murrell is always wearing a hat whenever he appears on the Screen Junkies or Movie Fights show. The one time he's not wearing a hat (because he was participating in a formal wedding ceremony), the comments section pretty much blew up with surprised exclamations about his (revealed) baldness.
In his show that shares his name, The Nostalgia Critic never takes off his hat. A bit of Real Life Writes the Plot, too: Doug Walker is prematurely balding. Most of his "modern movie reviews" usually have him wearing the Critic hat, too, as some people find his lack of hair distracting.
Fraser from Video Games Awesome! also almost always wears his purple cap unless he's costumed as a bald character. For some costumes that don't include any kind of hat, he wears an identical cap in a matching color.

Western Animation

Midgel from 3-2-1 Penguins! is almost never seen without some sort of headgear. If not his aviator hat, he'll inevitably be wearing something else.
Finn in Adventure Time always wears his hat. He didn't take it off until the second season, for a gag that revealed his long, blond hair. He has taken it off a few times since then, but he definitely prefers life with it on.
Amphibia: Sprig and Ivy are almost always seen with their hats on. It’s because they’re embarrassed of their hair. Also, for Spring, it was a gift from his late parents. Polly is also rarely seen without her bow on, although unlike her brother’s hat, it doesn’t seem to have much personal significance.
Fern from Arthur is never seen without a bow on her head.
In the Alvin and the Chipmunks cartoon, Alvin is almost never seen without his cap. This becomes particularly obvious in the movie parodies when he wears similar headgear appropriate to the character — even Alvin-as-Robocop has a metal version of the cap's visor sticking out of his helmet.
Big City Greens: Downplayed with Bill, who is almost always seen wearing his red truckers hat. However, there are a few instances where he is where he is seen without it on.
Bob's Burgers: Louise never takes off her pink bunny ears hat. She refuses to take it off during gym class. When she was a baby she wore a pink beanie. When her hat is stolen in "Ear-sy Rider," she wears a hoodie to cover her head and is distraught without it.
In Bojack Horseman, Todd always wears his yellow ski cap.
In Buzz Lightyear of Star Command, Buzz always has a purple helmet liner over his head that completely obscures his hair (or possible lack thereof), even in civilian clothes.
Camp Candy: Nurse Molly always wears her nurse's cap, even when she's not wearing her uniform.
Class of 3000:
- While Sunny and Li'l D's outfits include hats, this trope is actually averted with them, as their hats get removed or knocked off a few times in the series.
- Madison is a variant, as she's usually wearing a white headband, and on the rare occasion that she isn't, she has another item on her head instead.
- Downplayed with Philly Phil. He usually wears a purple headband, and when it is removed, he usually has something else on instead. However, a brief scene in the Christmas Episode does show his natural hairstyle.
- Played straight with Cheddarman, who always has some kind of hat on.
- The Eastley Kids wear distinct black-and-red, helmet-like hats.
Codename: Kids Next Door:
- Numbuh Five rarely takes her hat off; in "Operation: L.I.C.E.", when the Delightful Children replaced it with a decoy infested with mutant lice, she discarded it only long enough to get a new one. Other than that, if she takes it off it's in order to use it in some important way, like in "Operation: C.A.K.E.D.-T.W.O." when she threw it to expose a hologram.
- Likewise Numbuh 2 is rarely seen without his aviator's hat. It was temporarily destroyed in "Operation: L.I.C.E." but he had a new one by the next episode.
- Lenny of The Delightful Children from Down the Lane pretty much always wears a football helmet. He only takes it off in one episode where it turns out he's a double agent. Said helmet grows back after revealing he's a triple agent.
Launchpad McQuack from DuckTales (1987) and Darkwing Duck is rarely seen without his aviators cap. He often even wears it underneath a different hat (in some instances it looks like he's not wearing it under a different hat, until that hat comes off). In fact, how Launchpad looks without his hat varies on both shows. Sometimes he has a full head of hair, and other times he's bald, with only the hair that can be seen when he's wearing his hat. In the Darkwing Duck episode "The Battle of the Brain Teasers", when other characters pull on his hat they struggle with getting it off (though they do manage in the end).
Ed, Edd n Eddy
- Edd always wears his black toque and gets very concerned about being seen without it. When it actually comes off (which is never seen by the audience), the others are always shocked by what's underneath. When Ed and Eddy saw it, Edd actually threatens to never speak to them again if they ever tell anyone.
- In early episodes, Kevin also never took his hat off, and even bathed while wearing it! He's usually still wearing it in later episodes but will take it off if for normal reasons.
In The Epic Tales of Captain Underpants, Bo is never seen without his orange beanie (or an occasionally-appropriate substitute).
Meg Griffin on Family Guy is almost never seen without her hat. In one episode we see her alone in her room brushing her hair with her hat off. When someone else enters the room she scrambles to put her hat back on with as much urgency as a naked person would scramble for some Hand-or-Object Underwear.
All of the main leads of Gravity Falls wear some sort of headgear which they are rarely seen without. In Dipper's case, this is explained - he wears a hat to help hide his embarrassing big dipper-shaped birthmark. Dipper's hat somehow even manages to stay on when he's upside-down in the episode "Roadside Attraction".
Orko from He-Man and the Masters of the Universe (1983) never removes his hat, as part of the Trollan custom that they never show their faces to anyone except their one true love. When he and Dree Elle showed each other their faces, they were kept offscreen; only shadows were shown. In one comic book story, Skeletor magically disguised himself as Orko and blew his cover by taking off his hat. Even that was kept in shadow!
The children of Hey Arnold! who wear hats qualify, especially Arnold himself. There was even an episode dedicated to Arnold losing his hat and how strange he looked and felt without it. The reason why he's so attached to it is that it was a gift from his missing parents.
Inspector Gadget is never shown without his signature fedora. This is lampshaded in one episode when Penny finds it where he was supposed to be sitting and she notes how he never goes anywhere without it.
The CGI kid racers in The BBC's pre-school show Kerwhizz always wear armoured tracksuits with helmets.
The title character of Kick Buttowski never takes off his helmet. He loses it in one episode and tries to find a replacement, with his head being obscured by mud for the duration of the time between.
- Wade, one of Kick's acquaintances, is also never seen not wearing his beanie. He loses possession of it in one episode, but Scenery Censor is used so we don't see the rest of his face.
Kim Possible villain Professor Dementor is never seen without his helmet.
Dale Gribble of King of the Hill almost never removes his Mack cap. It's because he's ashamed of his baldness. On a couple of occasions when he's forced to remove it he tries to find another hat to cover it.
Quincy (a boy who likes to play musical instruments from Little Einsteins) generally is never seen without his a red and blue baseball cap. In fact, the rest of the team are wearing the same outfit in all episodes.
Except for the main protagonist Super Why! (or Whyatt), the Super Readers are never seen without any headgear in their super outfit and their normal outfit.
Les Sisters: Sammie is never seen without her yellow hat.
Dinky Little of The Littles is almost never seen without his aviator hat, though he took it off for the majority of "Ben-Dinky".
Ralphie in The Magic School Bus is always wearing a backwards baseball cap, only taking it off once or twice while sweating, or if the situation calls for him to wear a different piece of headgear (and even then he may still wear the hat underneath). He didn't even take off his hat when he got sick and confined to bed. Made even more bizarre by the fact that he's in an elementary school, which usually has rules against this sort of thing. He even keeps it in the reboot/sequel The Magic Schoolbus Rides Again.
My Little Pony: Friendship Is Magic:
- There's Apple Bloom, who usually wears a pink ribbon in her mane, but has also been seen wearing one of Rarity's hats, helmets, a blue bonnet, and a bunny costume (both from "Family Appreciation Day".) She and her older sister Applejack, who is seen often without headgear, have whole closets with identical ribbons and hats, respectively.
- Apple Bloom's nemesis Diamond Tiara has a Cool Crown that she never removes, even when she has to wear bunny ears too. The tiara even managed to stay put in windy weather.
Everest from PAW Patrol has hardly ever been seen without her toboggan.
Isabella Garcia-Shapiro of Phineas and Ferb is almost never seen without anything on her head, mostly using her pink hairbow. When she does wear a hat, people suspect her bow is underneath; this is proven in "Ferb TV" where she wears the red version of her bow under her beret.
- Played With: Perry the Platypus doesn't wear his fedora in "pet mode," but puts it on as soon as he switches to his job as a secret agent. It's a Running Gag that his Friendly Enemy, Dr. Doofenshmirtz, can't recognize him without it.
  - The gag gets exaggerated in the episode, "The Lemonade Stand." Perry shows up to Doofensmirtz's apartment disguised as a plumber, with nothing but a hat and belt, and Doofenshmirtz can't recognize him until he's wearing his fedora, and only his fedora.
  Doofenshmirtz: What kind of a plumber are you?!
  Perry: (Chatters and takes off plumber's hat)
  Doofenshmirtz: A platypus plumber?
  Perry: (Puts on his fedora)
  Doofenshmirtz: Perry the platypus plumber?
  Perry: (Takes off belt)
  Doofenshmirtz: [Shocked] PERRY THE PLATYPUS?!
Brucho from Plasmo refuses to remove his face-covering helmet, to the point of even wearing it in the bathtub. According to him, an alien woman once called him ugly, so he's kept the helmet on ever since.
Pocoyo:
- It's never revealed what Pocoyo looks like without that hat of his.
- Nina has her hair covered, but she shows some of her red hair on her forehead. In the music video "Fred's in Fashion", she wears a wig over her hat.
In Private Snafu, Technical Fairy First Class is never seen without his garrison cap.
Ready Jet Go!:
- Mindy Melendez is always seen wearing a hat, usually her bear-faced beret, and never takes it off once. She even wears a nightcap to bed.
- Mitchell Peterson never takes off his red checkerboard aviator hat.
Unlike other incarnations of the franchise, RoboCop is never seen without his helmet in RoboCop: Alpha Commando, except from the back in the opening.
Rocket Power: Twister's brother Lars is almost never seen without his trademark gray beanie, and when he doesn't wear it, his head is usually covered with a helmet when skating. Lars is only seen once without his beanie or helmet on in the episode "Bruised Man's Curve".
- Similarly, Raymundo is almost never seen without his trademark green fisherman hat or any other headwear on his head. It isn't until the episode "Twister's Hat", in which he is revealed to be bald on the top.
Rocky of Rocky and Bullwinkle almost always wears his aviator's cap, even when wearing another hat. Pretty much the only time he doesn't wear his cap is when he's wearing a night cap. In the "Upsidasium" storyline, after Boris steals Rocky's cap so he can impersonate him, Rocky keeps his night cap on until he finds his aviator cap, and switches hats so quickly that he can't be seen without it. At one point in the "Burried Treasure" storyline, when the guards at a bank think Rocky and Bullwinkle are trying to rob them, Rocky throws his cap in the air and puts it on a stick, representing a flag. Rocky's bare head is shown for a quick second before cutting to a close-up of the cap.
In Sea Princesses, the main characters are almost never seen without their crowns. In particular, Tubarina, the Princess of Sharks, and her cousin Marcelo are never seen without their shark-finned skullcaps.
Stan, Kyle, and Kenny from South Park almost never take off their hats. There doesn't seem to be a specific reason why for Stan, but in Kyle's case, it's to hide a really embarrassing Jewfro. Since his face reveal in the movie, Kenny is occasionally shown without his hood, but his face will always be either partially hidden by something, turning away from the viewer, or fully visible but the show will give no indication of who that blond kid even is. Cartman, however, is frequently seen without his hat.
- Kyle's dad Gerald is always seen with his yarmulke or another hat, even in scenes when he's otherwise naked.
- Craig Tucker is also always depicted wearing his blue chullo hat.
- Chef is almost always seen wearing a chef's hat, even outside of work.
Total Drama:
- Ezekiel wears his toque even while swimming. Fanon has often painted him as ridiculously attached to it; this is never really made clear in the show, but he's never seen without it until season 3 and after, by which point he's gone insane.
- Lindsay is never seen without something on her head. She usually wears a blue bandana, even when swimming, but she is also seen with a sleeping mask or a towel wrapped around her head. In her Total Drama Island promo picture, she wears a white headband and a pink flower.
Yugo from Wakfu is almost never seen without his hat on. In fact, the only other people who have seen him bareheaded are other Eliatropes. Underneath his hat however are a pair of wakfu wings
In The World of David the Gnome, a gnome never takes their hat off, as it's more taboo than being without their pants. It's based on Gnomes in Literature above.

Real Life

Truth in Television: Some religions and cultures require their adherents to wear certain headgear in some situations.
- A kippah (yarmulke) is a slightly rounded brimless skullcap worn by many Jews while praying, eating, reciting blessings, or studying Jewish religious texts, and at all times by some Jewish men. In Orthodox communities, only men wear kippot; in non-Orthodox communities, some women also wear kippot. Kippot range in size from a small round beanie that covers only the back of the head to a large, snug cap that covers the whole crown.
- Hasidic male Jews tend to always wear black hats in public.
- The keffiyeh/kufiya, also known as a ghutrah, mashadah, shemagh or (in Persian) chafiye, (in Kurdish) cemedani, and (in Hebrew) kaffiyah, is a traditional Arab headdress fashioned from a square, usually cotton, scarf. It is typically worn by Arab men, as well as some Kurds.
- Sikh men (and some women) wear the dastār, which most Westerners would recognize as a turban. While not directly required by the Sikh faith, it's become a de facto symbol and holds significant meaning.
- Some denominations of Christianity (and almost all Christian societies prior to the 18th century) require female members to cover their heads. The idea is that women are supposed to cover their heads while praying and that one should always be prepared to pray.
- Some Muslim women cover their hair with a headscarf when in the company of most people (usually men who aren't related to them).
- Orthodox Jewish married women cover their hair with a headscarf/wig/hat/etc. when in the company of most people (usually people who are not their husband), as do some Jewish women of other denominations.
Subverted by Terry Pratchett. He was well known for his penchant for wearing large, black fedora hats, as seen on the inside back covers of most of his books, but he actually took them off now and then. It's just that when he did, people assumed that it wasn't Pratchett. Perhaps it's a reference to his Discworld series? A wizard without his hat is naked. A wizard with his hat is not naked, even when he is.
Similarly, George R. R. Martin has his peaked cap as a major part of his image and recognizability, but does not, of course, wear it all the time.
Rapper LL Cool J is never seen in his music videos without some type of headwear on his head, most notably his trademark kangol hat. Even in the "Mama Said Knock You Out" video, his head is covered with a hoodie while he's rapping, as well as a towel when he's resting.
Actor Mike O'Malley, from Yes, Dear and Glee. Though he had a full head of hair early in his Nickelodeon career, his latter-day baldness has made him dedicated to the headwear and it's very rare to see him without a hat these days.
Singer John McCrea of the band Cake is never seen without some form of headwear. He appears to have an affinity for baseball caps.
Alex Erian of Despised Icon has not been seen without a snapback hat since 2007.
When he's not wrestling (and he hasn't for years), Hulk Hogan always covers his bald head with a bandana or do-rag, even a black option for testifying in court cases.
Randy Savage was also known for headwear, usually cowboy hats or bandanas and like Hogan, was rarely seen without them unless he had to take them off to wrestle. Also like Hogan and Mike O'Malley, he wore the headgear to cover up his bald spot.
The military of certain countries demand soldiers to wear their headgear, typically a beret, at all times when outside. Inverted when indoors and in certain events, where they're supposed to have them off.
The band The Residents never appear without full head coverings that look like a human eyeball, plus wearing a top hat.
Guy-Manuel de Homem-Christo and Thomas Bangalter of Daft Punk are always seen wearing full-coverage helmets.
Vlad the Impaler famously ordered the turbans of some Turkish ambassadors nailed to their heads because they'd refused to remove them.
Turkish messengers came to him to pay respects but refused to take off their turbans, according to their ancient custom, whereupon he strengthened their custom by nailing their turbans to their heads with three spikes so that they could not take them off.
Beginning around 2006, guitarist Jonny Buckland of the band Coldplay is never seen in public without a hat. This includes livestreams.
Given Country Music's affinity for the cowboy hat, many of the biggest names in the genre ranging from Kenny Chesney to Garth Brooks to Jason Aldean to George Strait are almost never seen without them. Chesney at least has the excuse of being Prematurely Bald.
Retired poker player Doyle Brunson, a native Texan, is almost never seen without his large white stetson.
Beach Boys frontman Mike Love began wearing hats almost constantly around the start of the 70s when his hair recession became far too obvious to ignore. He still wears them all the time today.
Until the 1960s and 1970s, in the Western world, headwear were worn by both genders and it was socially mandatory to do so.
The Black Angels frontman Alex Maas is always seen wearing a cap.

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