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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 threehundred-episode series doesn't qualify, even if his fedora was on all the time. (If you're still uncertain, just ask yourself if the creator seems to have made a deliberate choice to have the character in question wear headgear constantly. If it seems that way, then this trope is almost certainly being used.)
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.
Please Keep Your Hat On is related. Mostly overlaps with Nice Hat. Sometimes overlaps with The Faceless.
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Anime and Manga
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.
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 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.
From Keroro Gunsou, all Keronians have hats, usually a long-eared one with their personal symbol on it. One episode involved a notorious Unreveal when Keroro switches to a baseball cap after his hat is picked up by a toddler.
Chopper, who always wears his pink hat (later a blue and pink cap).
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 Gold 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.
Ash in Pokémon 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.
Inspector Megure in Detective Conan 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.
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.
Every single Smurf wears a white hat, except for Papa Smurf, who has a red one.
The titular main character from the British comic Buster was never seen hatless except for the final issue. Apparently, he looks just like Dennis the Menace (UK) under it.
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 a la The Blacksmith.
The movie adaption 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.
In 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.
"Little Edie" Beale in Grey Gardens wears scarves and other head covers throughout the documentary, having lost all her hair to alopecia.
In Elis List, Eli always wears a Botafoga snowcap while she's awake and a nightcap when she's sleeping.
In The Vampire Files, gangster Whitey Kroun got his nickname because he always wore a white hat, even as a teenager.
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!
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.
Live Action TV
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.
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).
Tenkaichi from The Conditions of Great Detectives 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.
The Swedish Chef of The Muppets is rarely seen without his chefs 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 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.
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.
From the same starting artist, as the example above, Chip in Hi and Lois.
For many years in Doonesburynote 34 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 thought the page quote to himself, 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.
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.
The titular character from ''Barnaby has a fairy godfather named Mr. O'Malley, who never ever takes off his hat.
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!"
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 in the 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 what he was based off of.
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 that part of their head (or, in the Pyro's case, any of his head) under it. Although for Demoman, one of them is a Funny 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 would be a lot shorter to list the Touhou 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—a yukkuri without an accessory is at best shunned by other yukkuris but is more commonly outright attacked by them. If she does not have a hat, she will die. Side materials do show that people usually take off their hats when indoors. 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.
Brain Dead 13: Averted in Vivi's Salon, when Vivi grabs Lance's baseball cap and uses it as a gag to ensure that he can't scream during the painful "makeover". Also averted in some death scenes.
In Pokémon X and Y, players can dress their characters in a variety of clothing, but they must always wear a hat of some sort.
In Guilty Gear, the mad doctor Faust is notable for wearing 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. But it is purposely hidden in shadow.
Jameson from Girls with Slingshots is always wearing a bandana. He even has a spare for laundry day. In one arc the girls try to get it off of him, and when Jamie finally grabs it off she finds another bandana. But under that they discover his big secret—he's almost completely bald.
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.
Rudy wore his cap even when hired by a theme park to live as a wild animal; i.e., naked.
Likewise, 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.
Black Hat Guy from XKCD. The only time he was bareheaded was when his hat was stolen (for about 2 strips).
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.
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.
The entire cast of Red vs. Blue is never seen without their helmets. In the last couple of seasons, most members of Project Freelancer are seen helmetless in flashbacks (excluding Agent Maine, who becomes the Meta), but the guys from Blood Gultch still never take theirs off.
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.
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.
Edd from Ed, Edd n Eddy. He actually gets very concerned about being seen without it, and when it actually comes off (which is never seen by the audience), the others seem shocked by what's underneath.
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 CGI kid racers in The BBC's pre-school show Kerwhizz always wear armoured tracksuits with helmets.
Kick Buttowski never takes off his helmet. He loses it in one episode (his head is covered with mud) and tries to find a replacement.
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".)
Her big sister Applejack subverts the trope by wearing a Nice Hat frequently, but still taking it off on occasion. A Funny Background Event gag later reveals that the sisters have a whole clostet full of identical hats and bows.
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.
The four main kids of South Park almost never take off their hats. In Kyle's case, it's to hide a really embarrasing Jewfro. Kenny never took off his hood, so no one knew what he looked like until he finally took it off in the movie. Cartman, however, is frequently seen without his hat.
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.
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.
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.
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 was taken away in "Ear-sy Rider," she wore a hoodie to cover her head.
Rocky of Rocky and Bullwinkle almost always wears his aviators 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.
Launchpad McQuack from DuckTales and Darkwing Duck was rarely seen without his aviators cap. He often even wore 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 his hat off they struggle with getting it off (though they do get it off).
Raven from Teen Titans Go! is almost never seen without her hood up. The only time she's seen hoodless was in the episode "Laundry Day".
Dinky Little of The Littles is almost never seen without his aviator hat, though he took it off for the majority of "Ben-Dinky".
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.
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.
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 wear their turbans whenever they're in public.
Some denominations of Christianity 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 is 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 takes them off now and then. It's just that when he does, people assume that it's not 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.
Actor Mike O'Malley, from Yes Dear and Glee. Though early in his Nickelodeon career he had a full head of hair, his latter-day baldness has made him dedicated to the headwear. Just try to find a recent picture of him without a hat.
Singer John McCrea of the band CAKE is never seen without some form of headwear. He appears to have an affinity for baseball caps.
Defied by many mothers and teachers. When their children or students won't take their hats off, they make them.