Hair that is striking in its length, volume, or color makes a very dynamic visual, and as such, many a work of fiction will include characters who have it. But wait! For some reason or other, the person with the striking hair needs to be disguised so that either other characters, the audience, or both don't realize it's them.
The easiest way to do this is to conceal their hair under a helmet, a wig, or with a hat, cap or scarf. This also gives the author the potential to toss out The Reveal with a dramatic explosion of flowing locks as the character's most prominent attribute positively identifies them for all to see.
Except...hair doesn't work that way. It can range from "fairly difficult" to "really freakin' hard" to successfully compact and store long or thick hair in such a small space. And even if it can fit, there's a real-life phenomenon known as "helmet hair" — hair that's been tucked up under a close-fitting piece of headgear for very long tends to be not so flowing and perfectly styled when it's released.
If The Reveal is particularly huge or unwieldy, it may result in Please Keep Your Hat On.
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Anime and Manga
Card Captor Sakura has an example in episode 7 with Yuuki Tachibana, who has waist-length hair that she hides under a baseball cap. This, combined with her tomboy nature, leads both Sakura and Tomoyo to think she's a boy until The Reveal at the end of the episode.
Enel and Sengoku form One Piece have their afro compressed under their headgears.
Revolutionary Girl UtenaThe Movie had Juri and Utena's character designs altered significantly. While Juri's hair has always been insanely elaborate, the volume of hair she fits in a simple fencing helmet (full French curls plus Rapunzel Hair that extends almost to her knees) is just ridiculous. Utena, by contrast, actually has character sketches that show how her relatively more modest length of hair could in fact be braided tightly enough to manage hiding it under her hat. Of course, when she takes her hat off it's not braided at all...
Even bigger than either of them is Anthy in the television series and the manga. Normally it's curled above her neck; when the third story arc begins, the viewers are shown that it's actually long, flowing, wavy hair, and it symbolizes her true self. In the movie, it's always down and flowing.
Taken Up to Eleven with Buddha from Saint Young Men. Though manageable when kept in his topknot, when he lets down it positively explodes outward until it's covered every floor, wall, and ceiling. It happened so quickly that Jesus thought a blackout had occurred.
C.C. of Code Geass does this almost any time that she impersonates Zero by wearing his outfit. Her waist-length hair just magically manages to fit into the Zero mask. Oddly averted later when everyone is wearing Zero costumes in R2, and C.C. has her green hair notably extending outside of the Zero mask in a way that'd easily identify her if not for the I Am Spartacus moment.
Averted in Elfen Lied. Lucy's helmet when she's in the lab is longer on the back, providing enough space to fit her hair, which goes past her waist.
Juliet of Romeo X Juliet could conceivably hide all her hair under her wig if she twisted and pinned it, but when she simply removes the wig and lets the long hair fall it's perfect and unbound. How she got it all up loose is anyone's guess, how it was let down unmussed is a small miracle.
Taiga from Toradora! has fairly long, poofy hair, but manages to get it done up in two small buns when she goes swimming.
In Halo Legends, the Spartan Cal manages to fit a surprising amount of hair into her helmet to make The Reveal more dramatic. It's also not shown to be bound in any way so it can flow dramatically. From the same series of shorts the Spartan Daisy is shown with a much more realistic bob that would be able to fit into her helmet.
Alto of Macross Frontier fits a high ponytail into his close fitting helmet. Either he has a special helmet with a hole cut for his hair or it's magic
In Gundam 00, Princess Marina Ismail is guilty of this when she goes on a world tour to negotiate a solar power generation system. How she keeps her butt-length hair rolled-up is anyone's guess.
Soma Peries also has this problem, but it's averted as the helmet on her customised pilot suit has a visibly larger helmet than the male pilots.
In Yu-Gi-Oh!, when Mokuba challenges Yugi during the Duelist Kingdom arc, he's wearing a disguise in which he manages to cram his three pounds or so of hair underneath a cap.
In a later arc, Valon, whose hair is both very spiky and extremely thick, somehow put all of said hair into a regular motorcycle helmet. His helmet hair is impressive but still impossible. Meanwhile, Marik - who also rides motorcycles, and is introduced earlier - averts this trope by having his long hair stick out of the back of his cheap helmet.
Hanaukyō Maid Tai. Cynthia keeps her hair loose, but on the very same head under the very same cap Grace keeps the very same hair, without changing the volume of the cap itself.
Sunday Spade of Jajauma Quartet (licensed as Wild Cardz in North America) manages to hide several meters worth of hair underneath a small cute cap.
Depending on who's drawing him at the time, Wolverine's flared mask could concievably contain his distinctively flared hairstyle (they're rarely drawn to actually match up, flaring-wise - in fact, the haircut came a while after the mask; he's never unmasked in his first appearances). The muttonchop sideburns are a different matter - some artists don't even bother to draw his mask covering the parts of his jaw where there's hair when he's unmasked. And how does his hair stay so distinctively flared when he keeps wearing a mask over it?
In Kyon Big Damn Hero, Tsuruya begins their first Curb-Stomp Battle by revealing her identity. She pulls off a blonde wig, and her ankle-long green hair drops to the ground. This is soon followed by Kyon and Yuki shifting into martial arts mode, and beating all 24 of their opponents into a lengthy stay at the hospital.
Arguably the second most popular interpretation of what's under Edd from Ed, Edd n Eddy's hat is the notion he has long hair that goes past his shoulders. Typically it's tied up using bobby pins or a ponytail.
Averted in Victor/Victoria, in that Julie Andrews has her hair cut that short to perfect her Count Grazinski look. Double averted in that the "drag reveal" involves a woman pulling off a long wig to reveal short, mannish hair.
Anya in Anastasia Appears to have a small ponytail for most of the movie, but when she lets her hair down later when she's all dressed up, her hair is much longer than the ponytail would account for. If you look closely, at the small "ponytail", though, you can see that it's actually only the ends of her hair sticking out of a very tight bun.
In She's The Man Viola impersonated her brother in order to get into a boys football team. She hides her hair under a boy-wig, which she removes in the movie's climax football match. Seeing the length, it makes one wonder.
In Shakespeare in Love, Gwyneth Paltrow's character managed to get her waist-length hair under a short wig so she could disguise herself as a teenage boy and thus play the part of Juliet, in which she let her real hair down.
In Disney/Pixar's Up, young Ellie takes off her flying helmet to reveal a bushy head of hair, made to look bigger by "helmet hair" and static electricity.
In The Princess and the Frog, Facilier's hair is about the same height as the hat he's trying to keep it under. Hat hair is almost certainly in effect.
Rapunzel in Tangled uses this as character development - when she enters the kingdom for the first time, the long hair she had to keep for Mother Gothel's sake is immediately an encumbrance to her joining in the festivities and Flynn recruits a group of young girls to braid it until it's compact enough to be off the ground. When Gothel tricks her into returning to the tower, the unbraiding of her hair is a subtle symbol of her return to Gothel's dominance over her.
Played for Laughs in Austin Powers in Goldmember: Foxxy removes the cap of her wetsuit to reveal short hair, then shakes her head, and the hair explodes (offscreen) into an afro.
In Brave, it is nothing short of miraculous how Queen Elinor manages to tuck all of Merida's profusely curly, waist-length hair under a small wimple that doesn't even bulge — and of course, when Merida reveals herself at the archery tournament, her hair flows as freely as if it had never been subjected to the accursed wimple.
Played straight during the Stark Expo intro in Iron Man 2. Lampshaded in the novelization.
In the X-Wing Series of the Star Wars Expanded Universe, there are a number of Twi'lek pilots. No mention is made of how they accommodate their brain-tails to their pilot helmets, though there are apparently "socks". But on at least one occasion, they dress up in stormtrooper armor, and the Twi'lek character is specifically commented on as probably being very uncomfortable with her sensitive brain-tails all scrunched up in the helmet.
The Lord of the Rings plays this straight when Éowyn removes her helmet at the climax of a pitched battle. Interestingly, though, The History of Middle-earth has revealed that in an early draft of Return of the King, Tolkien averted the trope instead—originally Éowyn cut her hair short before donning men's armour.
It's a non-issue in the Peter Jackson film adaptations, seeing as it's shown as quite normal for male Rohirrim to have long hair!
Edward Eager's children's novel Half-Magic has Katherine whipping off her helmet after defeating one of King Arthur's knights, with her long brown hair revealing that she is female . . . and also nine years old.
Spots The Space Marine has thick dark hair that comes down to her waist, yet she can tape it up so it fits under her helmet.
Jeri Ryan's hair is mid-back length, but she wore it tightly braided to play Seven of Nine on Star Trek: Voyager.
Inverted with the 60s Batgirl, whose long red hair was actually a wig to help further conceal the fact that she was secretly Barbara Gordon with the short black pixie-cut.
This is also how the modern Batwoman conceals her identity, hiding her short red hair under a long red wig.
The song "Signs" by Five Man Electrical Band has these lyrics:
And the sign said "Long-haired freaky people need not apply"
So I tucked my hair up under my hat and I went in to ask him why
He said "You look like a fine upstanding young man, I think you'll do"
So I took off my hat, I said "Imagine that. Huh! Me workin' for you!"
Also shows up in the Charlie Daniels song "Uneasy Rider." The narrator gets a flat tire while driving through Mississippi and has to stop at a redneck bar so he can call for repairs. He stuffs his long hair into his hat, trying to hide his counterculture leanings, but eventually has to take it off. The locals are not amused.
Millia Rage (Guilty Gear) is probably the most extreme example of this trope. Her hair naturally falls to her ankles while tied up, but she also uses it as a weapon, and it takes huge and ridiculous shapes. Also, in one winning pose, she takes off her ponytail and her hair flops to the ground, stretching to about two feet from her!
In-universe, explained by it not being hair but a magical symbiote permanently bonded to her which has a high-end Healing Factor. How it retracts again, though...
Noel Vermillion's (BlazBlue) long hair is usually kept up in a beret, somehow.
Same game, when Litchi Faye-Ling is not in battle mode, she usually kept her hair in a big, complex bun, with a yin-yang and panda 'hairpin' to keep it in place. If she's in battle mode, she ends up revealing a VERY long hair that nearly touches the ground, even in ponytail and she's standing (and she's tall).
Samus from Metroid certainly qualifies. This may be a reason they cut her hair in Other M.
Between the Morph Ball mode and her 200+ missiles, keeping a ponytail underneath her helmet is a minor trick.
Multiple members of Organization XIII in the Kingdom Hearts defy the laws of physics by managing to keep their Anime Hair hidden under their hoods. Vanitas hides Sora's gigantic 'do in a perfectly head-sized helmet, which is partially explainable by the fact that he doesn't so much as remove his helmet as transform it Also, Zack Fair can hide his big spiky hair under a Spartan style helmet. Ventus is a borderline example. Then there's Terra, who somehow crams all of his thick hair (which reaches to around his shoulders) inside his head-sized helmet. Though for Ven and Terra, the helmets are summoned on.
Cecil Harvey has a mane of long, flowing white hair under his Dark Knight helmet. Golbez also has long white hair under his horned helmet. Averted with Kain Highwind whose Dragoon mask has room in the back for his blonde ponytail.
Edea of Final Fantasy VIII in her first scene, where her long hair just disappears inside her headgear.
Ron Delite of Ace Attorney fame has hair that resembles cinnamon buns. Fans often wonder how it could possibly fit in his Mask De*Masque mask.
Custom character creation and Clothing Damage in Soul Calibur IV combine to allow this. You can give a character a huge afro and put a close-fitting helmet over it, and it'll magically be sucked into hammerspace. Until you break the helmet in combat, that is, at which point it erupts. Players have been known to lose matches from the distraction.
Waka from Ōkami somehow keeps his ankle-length locks completely hidden beneath his hat/helmet, which perches jauntily on the top of his head.
In World of Warcraft whenever players put on a helmet all of their hair disappears under it. The same applies if they put on a hat, even if their hair is three feet long and they're wearing a small cap.
Grand Theft Auto: San Andreas. The player can choose to get a giant afro, which remains entirely undamaged by the wearing and removal of any headgear.
Sougetsu Kazama (Samurai Shodown) besides using water ninjutsu, must know some of hair ninjutsu, since to make a column of water rise, his hair unties by itself as he turns gracefully. In one of his victory poses he actually unties his hair with one hand, and it just flows and flows until it actually reaches the floor! Amazing that he never used it to attack...
Judging by this piece of concept art◊ from Mega Man 8, Proto Man has some kind of enormous spiky pompadour/mullet hybrid '80s Hair that he manages to fit under his helmet. It still somehow manages to not be his most blatant violation of headgear sensibilities, thanks to wearing Cool Shadesunder the same shades on his helmet.
Your character in Guild Wars 2 can have long, flowing hair - or in the case of Sylvari, a couple feet of twigs sticking out of their head - but it all disappears entirely under helmets.
Nightfall in ElfQuest. She wears a headscarf most of the time, except when she's literally letting her hair down.
Cuanta Vida: How the heck does Jordi/Bleu/BLU Spy fit his poofy, scruffy hairstyle into his class's tight-fitting balaclava without making it look all lumpy? Early on it's fairly believable, but his hair gets pretty long as the comic progresses.
Collar 6: When Sixx's hair is in a pony-tail it reaches to her knees. Butterfly, aka Evita Kappel, also has this, having hidden her long, wavy black hair under a shorter blond wig.
Homestuck: Vriska Serket and Aradia Megido both have very long and unkempt hair. How they fit it all into their tiny God Tier hoods is anyone's guess. In a lesser case, Nepeta Leijon's hair is taller and wider than the tiny cat cap she normally wears.
When not wearing his green cap, Kyle Broflovski sports a huge "Jewfro" that's like twice the size of the hat that hid it. Afros and other curly hairstyles compress quite a bit, since much of the volume is down to the shape of the hair rather than its mass.
Similarly, in an episode of Duckman, Cornfed pulls off his rather small hat and an enormous afro-like hairdo comes ballooning into view.
Avatar: The Last Airbender just loves this trope. Zuko's Season Three shaggy emo boy mop can be tied neatly into a topknot; Katara's slim braid disguises hair so thick it is wider than her shoulders (which is actually realistic as her hair is wavy, and thus looks bigger than it actually is); Azula's little topknot/hair antennae combo, when let down, reveals waist-length locks, and Toph's modest bun is revealed to be a veritable afro when not properly done up; and in a reversal, Sokka's ponytail implies hair about shoulder-length, but when untied is barely level with his chin, and it's in a sort of wedge cut that would really be impossible to get into any semblance of a ponytail.
Comic Book Guy gets a bit of this in an episode as well. When Bart is haggling with him over trades, he offers to throw in his "man-scrunchie". Tied back, his hair seems to be your typical balding-guy ponytail. But once unleashed, it flows with volume and sheen worthy of Salon commercial.
And when the school staged a fake ceremony knowing Lisa will confess she cheated on a test to Comptroller Atkins who is awarding the grant money. The fake Atkins unmasks turning out to be Otto complete with his hair, hat and headphones.
It takes no time for Kim Possible to fit her waist-length hair under a helmet, even if it's automatically popped on her head by a gadget.
Shego's hairdo, on the other hand, outright shrinks by 50% the only time we see her out of costume.
There was one episode of Danny Phantom that had Sam donning a Gothic-like wedding gown. Her usual short hair suddenly seem to grow twice its size when styled into two wild ponytails. Rapunzel Hair Jazz once squeezed her entire hair inside the Fenton hazmat suit she was wearing.
One episode of King of the Hill had Dale telling a story of his version of events. In the story, his characteristic hat falls off revealing, not his usual bald head, but what can only be described as a glorious mane of flowing hair.
Ten from Batman Beyond has a rather voluminous head of blond hair, but in costume her head is as smooth as an egg.
Roger of The Life and Times of Juniper Lee is almost always seen wearing a blue beanie cap. When forced to take it off for picture day, he is revealed to have a truly epic afro. How epic? He needs help to get the hat back on.
Given a humorous twist in The Venture Bros.. A flashback to when the Monarch was just starting off as a villain revealed he used to wear a helmet instead of his crown/cowl look. The helmet wound up giving him compressed eyebrows, which poofed out when he took it off.
In the Futurama episode "Xmas Story", in a scene parodying The Gift of the Magi, Zoidberg, Amy (whose hair could easily lend itself to this trope), and Hermes are all wearing hats. Zoidberg offers Amy a set of combs, only for her to take off her hat and reveal she sold her hair to a wigmaker so she could buy a set of combs for Hermes. "Oh, the irony," says Hermes, who also reveals he sold his hair to buy a third set of combs for Zoidberg. Zoidberg thanks Hermes for the combs, then takes off his hat to show he now has Amy and Hermes's hair, exclaiming "Finally, I look as pretty as I feel!"
There is a Speedo long hair swim cap out there, sold on Amazon.com. Given that whoever is seeking to buy this wants to actually fit all their hair in that swim cap and for said cap to actually fulfill its purpose, that swim cap most likely fits this trope.
Even a regular Speedo silicone swim cap will accommodate over two feet of straight hair of average thickness, if it's braided and coiled.
Just braiding hair that's long enough to be braided can compress it to a small degree. However, as the number of strands in the braid goes up, so does the amount of compression of the hair that is braided. Braiding is especially good for achieving Compressed Hair if the hair is braided tightly, like Jeri Ryan did to act in Star Trek: Voyager
Any Sikh man wearing a turban. All Sikhs are required by religious obligation to abstain from cutting any of the hair on their bodies, ever. This requirement results in impressive lengths of hair. Since Sikh men are required to wear turbans, they are putting hair at least two feet long into that turban.
Some marching band uniforms require girls with hair past their shoulders to tie it back and shove it all inside their hats somehow. If it won't fit, it can be tucked down the back of the jacket.
Even with a loose bun it's not that hard to fit it all into a marching band helmet. Though some girls probably still have to cut their hair if it's really thick and curly.
Some people with long hair (usually women and girls) who wear their hair up and then let it down will sometimes get comments from people who are surprised to learn just how long their hair actually is now that it's down.
If your hair is straight, it may be surprisingly compressible, even if it's long. A lot of period hairstyles (and, famously, Princess Leia's double-buns) actually require extra padding or hairpieces, or sometimes backcombing and a lot of hairspray, to produce the volume of hair required. (A great many photos you see from the late 19th century, for example, are achieved like this- nobody admitting to wearing it, but Great Britain imported thousands of tons of hair in this period.)
Basically, how easy this is varies quite a lot from person to person depending on how thickly their hair grows and how thick the strands are.
Anyone who's ever worked in theater and was required to wear a wig has developed some impressive tricks to hiding their hair. Between pins, braids, coils, and caps, it's possible to hide quite a bit of hair under a wig. Watch this video through to the end to see how much hair Kristin Chenoweth hid under her Sally Brown wig.
Unzie the Albino, an New Zealand aborigine who toured with Barnum and Bailey, was capable of fitting this◊ under a top hat.◊ You might not have wanted to sit behind him in the theatre either way.