[[quoteright:275:[[Disney/{{Mulan}} http://static.tvtropes.org/pmwiki/pub/images/sweetmulan.jpg]]]]
[[caption-width-right:275:Mysterious as the dark side of the moon.]]

->''"As sweet Polly Oliver lay musing in bed,\\
A sudden strange fancy came into her head.\\
Nor father nor mother shall make me false prove:\\
I'll 'list as a soldier and follow my love.''

->''So early next morning she softly arose,\\
and dressed herself up in her dead brother's clothes,\\
She cut her hair close, and she stained her face brown,\\
And went for a soldier to fair London town."''
-->-- '''English Folk Song'''

A female character dresses up as a man to accomplish some end. Often becomes a variant of the JackieRobinsonStory. The sports version is especially popular in children's media, since it allows for an {{Anvilicious}}ly contemptuous boys' team for the heroine to win over with her talents.

Named for the old, old folk song "Sweet Polly Oliver" (quoted above), in which a woman disguises herself as a man so she can join the army and follow her soldier lover. However, the trope predates the name, going back apparently to a [[OlderThanPrint 6th century AD]] Chinese myth.

If a girl dresses like that all the time, she might be a WholesomeCrossdresser. Sometimes the audience (or a character) doesn't know this at first, and is surprised to find out SamusIsAGirl.

Contrast with HarmlessLadyDisguise and DisguisedInDrag; is a type of SheIsTheKing (Type 1, to be specific). Some men may subconsciously see through this, and become SweetOnPollyOliver. Since, in most cultures, she needs a new name, may occasion a MeaningfulRename. Not to be confused with {{Bifauxnen}}.

Many times when this is done in film and TV, the actress playing the crossdressing character rarely does a convincing job (see HollywoodHomely), requiring SuspensionOfDisbelief on the part of the audience that the other characters encountering her really believe she is a man/boy. On the other hand, quite a few women really did get away with this surprisingly easily in the past, which ''The Folklore of Discworld'' phrases as:

->in an age before unisex fashions, trousers meant 'man' and skirts meant 'woman'. Trousers plus high-pitched voice meant 'young man'. People didn't expect anything else, and saw what they expected to see.

As a type of WeirdnessCensor, the human mind will simply ignore small details that could give the ruse away, once it has classified a person as either male or female. And in societies in which male and female gender roles are clearly separated with no room for overlaps, this effect would be even stronger, as the idea of meeting a crossdresser would be even more inconceivable than it is today.

You can listen to the full version of the song [[http://www.youtube.com/watch?v=icx9_jpHg3I here.]]



[[folder:Anime & Manga]]
* Ikusu Mizutani from ''LightNovel/KonoNakaNiHitoriImoutoGaIru'' hides the fact that she's a woman while working for the Seiryuu Association. She does this not because she has to, but so as to keep up the illusion of her dream of being a ninja, as all ninjas were traditionally male.
* ''Manga/{{Basara}}'': The story takes place in a future Japan, reduced to a barren desert by a catastrophe at the end of the 21st century. The main character is Sarasa, a girl whose twin brother, Tatara, is prophesied to be the "child of destiny" who will bring back the country's independence and stop the tyrannical rule of the Empire, namely the Red King. When Tatara is killed, Sarasa pretends to be him in order to keep the downtrodden from losing hope.
* One of the major plot points of ''Manga/OuranHighSchoolHostClub'', with the twist that Haruhi wasn't ''trying'' to pass as a boy, she was just wearing castoff men's clothing because she couldn't afford her school's expensive uniform, and didn't care enough to correct the members of the Host Club when they jumped to conclusions about her gender. A good half the comedy of the series springs from the boys of the Host Club running themselves ragged to keep Haruhi's gender a secret from the rest of the school, while Haruhi herself continues to not care.
* [[spoiler:Akira]] in ''Manga/MaiHime'' disguises herself as a man. In [[ShesAManInJapan the German version of the dub]], she's even given a man's voice (and not even [[CrossdressingVoices a woman playing a man's voice]], at that), as the production company was not aware "he" was actually female...
* ''Manga/RanmaOneHalf'':
** Akane disguises herself as a boy in order to battle the Yamata no {{Orochi}} without being eaten as the beast loves the taste of women.
** Ranma's UnluckyChildhoodFriend Ukyou "gave up" her femininity and passed herself off as a male (to the point of attending a boys-only school) after Genma and Ranma ran out on her marriage arrangement. Once her ruse is discovered, however, she quickly abandons the pose and crosses over into WholesomeCrossdresser territory (but only at school, her "civilian clothes" are all feminine [[{{Bokukko}} even if she still acts boyishly]]); later that season (in the anime only) she even abandons that once, causing all of the boys at Furinkan High to wonder who the "cute girl" is. She wears the girl's uniform at least once after that (and lampshades it, naturally.)
** In a strange subversion of the trope, [[GenderBender girl-Ranma]] had to disguise herself as ''male'' during a martial arts duel to hide the fact that she had been locked as female.
* Juliet Fiamatta Asto Capulet in ''Anime/RomeoXJuliet'' dresses as a boy named Odin to disguise her connection to the Capulet family line, as the last surviving member is known to be female. After Juliet learns of her heritage, she's allowed to wear dresses and let her hair down when she's in the Capulet headquarters and away from intruders, and she takes it on stride. (Then again, when she pulled a RecursiveCrossdressing stunt at the start, she ''did'' like [[SheCleansUpNicely wearing a fancy gown.]]) [[spoiler: And once Juliet's identity is revealed to the public and ''everyone'' knows who she truly is, she just doesn't bother with disguises anymore and wears either simple dresses or tomboyish clothes depending on the situation.]]
* In ''Manga/KazeHikaru'', the main character Tominaga Sei disguises herself as a male swordsman after the murder of her family to avenge herself on their killers, and ends up joining UsefulNotes/TheShinsengumi.
* Michel Volban of ''Anime/GlassFleet'' is a noblewoman who assumed her older brother's identity and his role as leader of LaResistance.
* An early episode of ''Manga/CardcaptorSakura'' has a minor character named Yuuki dress up like a boy while she tries to remove a card's influence from her DisappearedDad's painting. Sakura doesn't notice her gender until the girl's NiceHat falls off and reveals her long hair.
* In ''Manga/CynthiaTheMission'' Shii, the male 'protection' personality of the busty and beautiful Kanae manages to pull this off with a specific jacket designed to minimize her bust. It doesn't help that Shii acts very much like a man.
* Subverted in ''Manga/LudwigRevolution''. [[spoiler: When we see a {{flashback}} of a princess being outcast and then flash forward to Petronella calling Julius "Julianna", this is where your mind goes, right? Turns out the young Princess Julianna is a [[{{Transgender}} trans woman.]] Maybe.]]
* Subverted in ''Manga/GirlsSaurus'', where all the other students at the boys' school Tsubasa goes to are convinced he's actually a girl pretending to be a boy, even though he isn't... Except for tough guy Arahata, who refutes the idea as ridiculous. "What do you think this is, a shoujo manga?" Of course, then when he goes to confront Tsubasa on the matter, he's utterly convinced that he's a girl after one look at him, too. He also gets molested by men on the train to school.
* Subverted in ''Manga/ShugoChara'': When Nadeshiko's "twin brother" Nagihiko shows up in one episode, it seems painfully obvious, that it is her in disguise... [[spoiler: until it is revealed that actually EVERYTHING ELSE was the disguise and Nagihiko is Nadeshiko's REAL identity.]]
* Done in the ''Manga/SailorMoon'' manga by Minako. She uses the Crescent Compact to transform into a male Mugen Gakuen student so she can slip into the school and watch the concert of idol [[PaperThinDisguise Mimi Hanyuu]], who is secretly [[ThePsychoRangers Mimette.]] She also does this at least once in the prequel, ''Manga/CodenameSailorV''.
** In the manga, both Nephrite and Sailor Moon did this--Nephrite as a ghostly bride, and Sailor Moon as the ghostly bride's groom.
** Sailor Moon also disguises herself as a reporter in the first-season [[Anime/SailorMoon anime]] episode "Cruise Blues". If that isn't obvious enough, look at how short her hair is in this disguise!
* Anne, a runaway girl in Part 3 of ''Manga/JoJosBizarreAdventure'', tries to pass herself off as a runaway boy to sneak onto a boat and travel the world, believing that it would be impossible to pull off such a disguise once she started to physically mature.
* Shizu, Mariya's twin sister in ''Manga/MariaHolic'' is doing the exact opposite of her brother by playing out this trope. None of her antics over at Mihoshi no Mori Boys' School have been seen, but this is especially troubling for Shizu since she DoesNotLikeMen.
* Yellow successfully passed herself off as a boy for the bulk of ''Manga/PokemonSpecial's'' Yellow chapter. Most characters didn't find out until the Gold and Silver chapter, though.
** RED (and the cast introduced in the GSC Arc) didn't know Yellow was a girl until the end of the GSC Arc. Most everyone else already knew by the end of the Yellow Arc.
* ''Anime/OtogiZoshi'': Hikaru disguises herself as her brother, because he is sick [[spoiler: and later dead]]. The series loses a bit of charm when she drops the disguise.
* Mizuki Ashiya from ''Manga/HanaKimi'' who dresses up as a guy to get together with her favourite high jumper, Sano. They get close enough that people mistake them for Yaoi Guys and even Shuichi (the loud guy...) starts liking her thinking she's a guy, leading to some odd situations to say the least.
* Kiri in the manga ''Never Give Up'' poses as a male model so she can stay close to her neighbor and love interest, Tohya. It helps a lot that Kiri already [[{{Bifauxnen}} looked just like her dad, who was a model too]].
* The incredibly {{Bifauxnen}} Oscar of ''Manga/RoseOfVersailles'' dresses as a man for her day job of commander of the Royal Guard. The rest of the time, she just does it because her father [[RaisedAsTheOppositeGender raised her as a boy]].
* Candy White-Andree in ''Manga/CandyCandy'' [[YouAreGrounded is grounded]] during a school festival, but a friend of hers sneaks her a box with two outfits: a female gown and a male disguise, both with matching wigs. (A gift from her MysteriousProtector, who had sent it ''before'' she was punished.) She uses them to sneak away and have fun without being caught by the school staff, alternating between the girly girl facade and the boyish one. HilarityEnsues.
* Kyouko from ''Manga/SkipBeat'' does this when she is challenged to act as the challenger's son.
* Rei [[ShoutOut Saotome]] in ''Anime/YuGiOhGX'' pretended to be a boy in her first appearance. Like in the ''Manga/CardcaptorSakura'' example, she's found out when she loses her hat and this reveals her RapunzelHair.
* Part of the backstory for Override of ''Anime/TransformersCybertron'' was that she somehow disguised herself as a boy to enter the great race for planet leadership. The weird bit, aside from the concept of a crossdressing robot, is that Override is pretty damn androgynous anyway and is a male in the original Japanese.
* "Pierre", actually Valerie, is a [[VillainousCrossdresser villainous version]] on ''Anime/AgentAika'', whom the titular character [[SweetOnPollyOliver falls for]].
* Briefly becomes very common during the earliest (chronological) arc of ''Manga/{{Ooku}}: The Inner Chambers'' as numerous heads of noble houses, seeing a {{gendercide}} plague kill off their sons and nephews, mask the absence of [[HeirClubForMen male heirs]] by dressing their daughters in drag and bringing them to public events like annual oaths of fealty to the Shogun. Then one year the screen hiding the [[ElCidPloy elusive]] Shogun Iemitsu is raised and a young woman (complete with a kimono, makeup, and a wig to mask how short she had been keeping her own hair) [[AwesomeMomentOfCrowning commands all present to behold their ruler]].
* In ''Manga/{{Naruto}}'' the male daimyo Sagi is eventually revealed to in fact be his twin sister Toki. After her brother's mysterious death, she swore to avenge him; to do so, she assumed the role of her brother and claimed the body that was interred was herself. Once her family's enemy was revealed and eliminated she revealed the truth of her deception to the people and continued in her role as daimyo.
* In ''Manga/GirlGotGame'', Kyo is forced/convinced by her father to pretend to be a boy so she can fulfill his dreams of playing basketball. She also lives in the boy's dorm with a boy she hates [[spoiler: who she of course ends up falling for.]]
** This series is pretty much a parody of the genre. Similar to the example in ''Mulan'', Kyo has many severe male stereotypes she tries to emulate with little success. She ends up adapting, however, and wonders if she can ever go back to being feminine. Her roommate also has an interesting way of coping once he discovers her true gender.
* Charles/[[spoiler:Charlotte]] Dunois of ''LightNovel/InfiniteStratos'' disguises herself as a boy while attending the school, [[spoiler: with the purpose of stealing data from [[ThatOneGuy Ichika]] and his [[PoweredArmor IS unit]]. Unfortunately, she got found out ([[FullFrontalAssault and in the most awkward way possible]]) before she could succeed.]]
* In ''Manga/{{Claymore}}'', Clare disguises herself as a man for a time in order to travel under the radar, even using her limited ShapeShifting abilities to elongate her vocal cords and deepen her voice.
* ''LightNovel/MayoChiki'''s premise.
* [[spoiler: Helmut Marx Von Babel]] of the Baselland Military Academy's cavalry divsion in ''Manga/GunkaNoBalzer''. Her sex isn't discovered until the protagonist forces her to strip to [[{{Squick}} remove the leeches that got all over her when she forded a river]].
* Itsuki Myoudouin from ''Anime/HeartcatchPrettyCure'', taking her big brother Satsuki's role due to the aforementioned man having a weak heart. For added "hilarity", Satsuki is also a case of DudeLooksLikeALady. He got better after a risky treatment, and Itsuki was able to resume being a girl by the end of the show. It should be noted that while Itsuki is mistaken for a boy several times in the series, pretty much everyone in the school knows she's a girl. [[EvenTheGirlsWantHer Not that it matters much ...]]
* Tsukiko from ''Manga/SamuraiHighSchool'' switches places with her [[HalfIdenticalTwins Half-Identical Twin]] brother Kou to enter said high school and become Supreme Commander of Japan. It helps that they both are adept at the opposite gender roles.
* [[spoiler: Alicia "Jeudi" Brandel]] from ''Manga/HonooNoAlpenRose'' must do this in the manga [[spoiler:to go to Austria unnoticed, calling herself "Julian", so she can escape from her StalkerWithACrush and find the people who can tell her who she truly is. She does it so well that two girls find her boy self "handsome", and one of them (Liesl) is quite infatuated with "him" too... And she may have been a bit infatuated wuith Jeudi ''[[IfItsyouItsOkay after]]'' [[IfItsyouItsOkay finding out]], too.]] [[{{Bowdlerize}} Sadly, it was cut from the anime.]]
* Despite female samurai and daimyo being not just allowed but commonplace in ''LightNovel/TheAmbitionOfOdaNobuna'', [[spoiler:Asai Nagamasa]] pretends to be a man for unclear reasons. Her "wife" is actually a boy, as well. Neither of them knew this when the (political) marriage was arranged.
* Mikusa from ''Manga/ArataKangatari'' must disguise herself as a male of the Himezoku for reasons she does not disclose to Kotoha. [[spoiler:She's eventually forced to reveal to Hinohara that it is because she's not even truly of the Himezoku.]]
* Kei from ''Anime/IriaZeiramTheAnimation'' looks like a tough-talking street rat of a boy (it's meant to make Kei look tough) until Fujikuro's sharp nose picked up the truth about ''her''. This makes things interesting since Kei is also attracted to Iria, though most figure it to be Iria being [[CoolBigSister someone to look up to]], much as how Iria looked up to her brother Gren in her youth.
* The heroine of ''Anime/CastleInTheSky'' dresses as a boy to evade capture. The disguise doesn't fly for long.
* In ''Manga/TheWorldIsStillBeautiful'' for a while starting from Chapter 31, Nike goes under disguise as "Vice Captain Kanaris Micaine" of Livius' army to pretend to be Luna's lover so they can stop her unwanted arranged marriage to Marquis Fortis. It fools everyone [[spoiler:but him, so it turns out]].
* In ''LightNovel/TokyoRavens'' Natsume is a boy as far as anyone outside of her family knows due to family tradition. [[spoiler:The "tradition" was created so that the family's enemies would target her rather than the actual heir, Harutora]].
* In ''Manga/TokyoGhoul [=:Re=]'', it is eventually revealed that [[spoiler: Kanae von Rosewald]] is actually a woman that has spent the last decade living as a man. She adopted her male identity because of the [[HeirClubForMen deaths of her brothers]], believing it was her responsibility to carry on the family legacy in their stead. Though it seems to be an OpenSecret, the man she loves is oblivious and she persists in hiding it from him. [[spoiler: Just before her death, she confesses her true feelings and Shuu finally calls her by her real name, Karren. She sacrifices herself to save him, and thinks how painful it was to live that way and how happy she is to be able to [[DyingAsYourself die as herself]]]].
* The YuriGenre oneshot ''Liar and the Ferris Wheel'' is about a girl that falls in love at first sight with another girl and pretends to be a boy to go on a date with her. [[spoiler:She knew the entire time though.]]
* ''Manga/NozomuNozomi'' is about the evolution of a middle school boy from WholesomeCrossdresser to Sweet Polly Oliver under the influence of female puberty over the course of a year following an inexplicable GenderBender. Nozomu starts out identifying as a boy who likes to dress as a girl in private but eventually ends up identifying as a girl who is forced to dress as a boy in public who feels she must maintain the pretense because she's afraid of the consequences of revealing her true gender.
* In ''Manga/Classi9'', Ren has to pass as a boy named Rentarou to keep studying music in [[OneGenderSchool Melite]]. Except for Mozart, who led her there and ended up becoming her SecretKeeper, no one is allowed to know about her gender, or they will both be expelled.

* In the Literature/{{Child Ballad|s}} ''Literature/TheFamousFlowerOfServingMen'', the heroine's husband and baby are killed by her mother, and she disguises herself as a man to run away and work.
* In the Literature/{{Child Ballad|s}} ''[[http://www.sacred-texts.com/neu/eng/child/ch063.htm Child Waters]]'', the heroine refuses to leave the hero, despite his declaration that he goes to woo another woman. He insists she dress as a footpage and run alongside his horse.
* In the Literature/{{Child Ballad|s}} ''[[http://www.sacred-texts.com/neu/eng/child/ch103.htm Rose the Red and White Lily]]'', the sisters dress as men to escape the WickedStepmother and rejoin with their stepbrother lovers.
* Yet another one (''[[http://www.sacred-texts.com/neu/eng/child/ch150.htm Robin Hood and Maid Marian]]'') has Marian seek [[RobinHood Robin]], armed and in man's clothing, and when the two meet Robin is also disguised - so they fight, for "at least an hour or more", before recognizing each other.
* Crossdressing is a classic folk music trope. One song, "The Soldier Maid," also known as "Female Drummer" (not sure whether it's true folk or modern) is about a girl who joins the British army as a drummer boy, and is only betrayed when a woman comes on to her, learns she's female, and goes off to tell her officers. The officers are actually disappointed they have to send her home, and give her a bounty and pension for her service. The song "Cruel War," covered by Peter, Paul and Mary, focuses on a woman who follows her love to war and is killed while in disguise.
** "Jackaroe" is another song about a girl who goes off to war to follow her love, this time in the Navy.
** As is "Billy Taylor", but it has a twist ending. It turns out that the titular character, whom the song's main character has joined the Navy to follow has found a new girl, and the main character tracks them both down and kills them, and is promoted for it.
** "The Handsome Sailor Boy" -- In which a young woman signs on a ship as a cabin boy and the captain falls in love with her. In some versions, she's looking for her lover and doesn't tell the captain she's a woman, until she's safe on shore. In others, she's just doing it for the adventure, both the captain and the captain's wife fall in love with her -- but it's only the captain who realizes she's a woman ... Until one night, on board ship, when she gives birth. Then everyone knows.
** In "The Female Rambling Sailor", a woman goes to sea after her lover is pressed into naval service and drowns. She proves an exemplary sailor, and none of her crewmates suspect her identity until she dies in a fall from the rigging and they discover her 'female form'.
* There's a Spanish ballad about a girl who dresses like a man, calls herself Don Martín and goes to war because her father is [[RetiredBadass too old]]. Then, the prince falls for her (getting extremely confused because he somehow suspects "he" is a girl, but isn't quite sure). Then the prince comes out to the queen and she suggest several tests to expose Don Martín, all of which fail, except the last one: a bath. Don Martín runs away and the prince after her, and they marry.
* ''Grażyna'', a 1823 narrative poem written by Adam Mickiewicz features an eponymous heroine living in the 15th century, who, as a protest against her husband coming to an agreement with [[UsefulNotes/TheTeutonicKnights Teutonic Knights]], secretly puts on his armour and leads the army into battle with the enemy.
** This poem is said to have inspired the Emilia Plater, a real-life military heoine of the November 1830 uprising against the Imperial Russia. Plater cut off her hair, put on a men's uniform and equipped a unit of more than six hundred volunteers - half trained soldiers and half peasants with war scythes. It's a significant fact that Plater had been also immortalized by Mickiewicz in his poem ''Śmierć pułkownika'' (''The Death of the Colonel'')
* Spoofed in W.S. Gilbert's ''[[http://math.boisestate.edu/GaS/bab_ballads/html/bumboat_woman.html The Bumboat Woman's Story]]''. The heroine disguises herself as a man to sign on as a sailor on the gunboat of handsome Lieutenant Belaye, whom she loves. When Belaye returns from leave with a wife, it is revealed that ''every one'' of the sailors on the boat is a woman who disguised herself for the same reason.
* Played with in ''Martinmas Time,'' in which a girl is [[IGaveMyWord forced to swear]] she will visit a camp of nearby soldiers. [[ExactWords She arrives dressed as a soldier]] and demands entrance. Impatient for the girl to show up, the soldiers tell her to hurry up and leave, even paying her to do so. At which point she reveals her disguise, ties her garter to their gatepost, and escapes.
* Deconstructed in Elizabeth Barrett Browning's ''The Romaunt of the Page'', where a lady accompanies her husband on a crusade, disguised as a page, only for the husband to declare that such an act "unwomans" a woman and that he'll only think of her as a page and never as a wife. The woman [[DownerEnding breaks down and sacrifices herself when they are ambushed by the Saracens]].
* Also in the different versions of Norwegian ballad ''Liti Kjersti Stalldreng'' (Little Kirsti Stableboy), where the heroine disguises herself for nine years as a stable boy in the royal stable. The prince goes SweetOnPollyOliver, and the result reveals itself when the king finds the clever stable boy in the stable, giving birth. He recognizes the relation, and accepts Kirsti as his son´s wife.

[[folder:Comic Books]]
* ''ComicBook/TheSandman'': [[spoiler: Jim the "cabin boy" in ''Hob's Leviathan'' is actually a girl named Peggy.]]
** There's also Desire, who switches genders as necessary.
* ''ComicBook/{{Marvel 1602}}'': Carlos Javier has a page named John Grey. Scott Somerisle is insanely jealous of "John"'s friendship with Angel, much to the latter's confusion. [[spoiler: When Scott finds out that Angel honestly didn't know that "John" was female, he apologizes... only to be told that Angel was, in fact, in love with Jean's boy-persona.]]
* In ''ComicBook/{{Legion Of Super-Heroes}}'', Lightning Lass made her first appearance pretending (rather inexplicably) to be her dead twin brother, the Legionnaire Lightning Lad. The deception was exposed when Sun Boy noticed that she didn't have an Adam's apple.
* In ''[[ComicBook/JusticeLeagueOfAmerica Justice League Task Force]]'', there's Mystek, who wore a very masculine armored suit. One of her teammates, Triumph, found out the truth on a trip through space. Mystek, who got claustrophobic when in costume, hid in the bathroom to take it off. Triumph eventually demanded that she come out, having had enough time to "drain the weasel". He opened the door, saw the indignant lady inside, walked back to his seat in a daze, and whispered, "''[[SamusIsAGirl Mystek has no weasel.]]''"
* The Spanish comic magazine ''ComicBook/ElJueves'' had a story, ''Emili[[strike:a]]o'' where a girl, Emilia, pretended to a boy to do the mandatory conscription in the Army and be with her boyfriend.
* Echo from ''Comicbook/NewAvengers'', who posed as a male hero named Ronin in order to infiltrate the Tokyo underworld. It was an ingenious move, especially when you consider that if gangsters were looking for a male hero with a ''very'' [[CaptainEthnic Japanese-sounding name]], a small Latina woman would be the last person they'd suspect.
* Agnès de Roselande/Isabeau de Marnaye in the Francois Bourgeon's historical series ''ComicBook/LesPassagersDuVent''.
* In one ''ComicBook/WeirdWarStories'', a drummer boy being held in a UsefulNotes/AmericanCivilWar prison camp turns out to be a girl, leading to a SweetOnPollyOliver'' situation. And then zombies attack...
* "Jack", in the ''Deathwatch'' comic strip by Creator/PaulCornell (Elizabethan ''ComicBook/JudgeDredd''), is quite clearly a girl wearing a false moustache to work as an actor. And, inevitably, [[RecursiveCrossDressing ends up playing Helen of Troy]] in ''Theatre/{{Faust}}''. Surprisingly, while the FishOutOfTemporalWater acts as OnlySaneMan to the MedievalMorons in just about every other respect, this is the one point where he has a blind spot as well.
* Subverted in ''ComicBook/DemonKnights'' with the Shining Knight (who is a Sweet Polly Oliver in some other versions as well). Her costume looks convincing to the reader (due to the fact that she's very flat-chested) but fools ''no one'' in-universe. And then played with further when [[spoiler: it turns out assuming she's a woman is wrong as well; she's non-binary in some way (nobody in the setting has the right terminology; she describes herself as "both").]]
* As a young girl, Martha Washington in ''ComicBook/GiveMeLiberty'' habitually passes herself off as a boy to avoid being sexually assaulted. She then gets grabbed by someone ''looking'' for young boys.
* [[ComicBook/{{WITCH}} W.I.T.C.H.]]:Vicky and Irma in the World Cup/Football Special. They posed as boys so they could play on the football team.
-->Cornelia: What should we call you? ''Irmo''?
* In ''ComicBook/PrinceOfPersiaTheGraphicNovel'', when Shirin leaves the city of Marv in search of LaResistance, she cuts her hair and masquerades as a boy named Shapur.

[[folder:Fan Fiction]]
* In ''Fanfic/{{Austraeoh}}'', the stallion [[spoiler:caravan guard Gold Plate turns out to be not so much a stallion at all; he's a mare called Gold Petals]].
* In ''FanFic/TheLostGirl'', Friendly has a variant of this, as she quickly forgets she ever was a girl.
* There's more than one ''Webcomic/AxisPowersHetalia'' fic out there that imagine the female Nations as being forced to do this out of necessity (i.e. avoid getting raped by their own soldiers), though this usually happens in historical-themed stories to stress the ValuesDissonance.
* In ''Fanfic/ChildrenOfTime'', [[WesternAnimation/SherlockHolmesInTheTwentySecondCentury Beth Lestrade]] dresses as a street boy out of necessity when in VictorianLondon, first to join Literature/SherlockHolmes on a case, then for purely practical reasons when she and the Irregulars are on the run. To her amusement, [[InspectorLestrade her own ancestor]] falls for her disguise, though she later confides to Holmes that she was rather surprised it worked.
* This is a popular trope in RuleSixtyThree fics in general.
* In [[FanficRecs/MartinMystery The Red Monarch]], Tatsuki does not actively try to hide her gender, but the short hair, baggy clothes - and presumably androgynous appearance - make everyone mistake her for a very cute boy at first.
* In ''[[http://www.fanfiction.net/s/6159955/14/Wolf-Cub Wolf Cub]]'' girls weren't allowed to be on Quidditch teams during Harry's parents' schooldays due to prejudice, so Remus' half-werewolf sister dressed in a boys' uniform and called herself Tam O'Flahearty in order to participate in tryouts. She won a spot as Seeker, pushing Harry's father, who was also trying out into the vacant Chaser position.
** A similar premise is used in ''[[https://www.fanfiction.net/s/10305847/1/In-Love-of-Quidditch In Love of Quidditch]]'' where girls aren't allowed to fly ''at all'' because it isn't considered "ladylike." In this case, Harriet Potter goes to Hogwarts, which her twin brother Alexander was supposed to attend, as "Harry" Potter in hopes that she can play professionally someday, while her brother attends the no-Quidditch academically-oriented school their father was sending her to so that he can become a curse-breaker.
* In ''Fanfic/{{Emergence}}'', Ruby is chosen to be part of a mission in Syria dealing with [[StrawMisogynist ISIS terrorists]] because with her short hair, she can pass for a boy at a distance with the help of baggy clothes.
* In the Manga/{{Naruto}} story ''Fanfic/SpiderThread'', Tomoe pretends to be a boy while traveling because she thinks it would be safer. The ruse continues long after it's necessity is gone.
* While not a precise example, this is a popular theme in a large number of Manga/{{Naruto}} with Haku as a major character.
* In the Literature/TheHungerGames fic ''[[https://www.fanfiction.net/s/8610425/1/What-s-So-Civil-About-War-Anyway What's So Civil About War, Anyway?]]'', Katniss joins the Union army by hiding as a boy called Kat. Somewhat subverted in that it does not take long for most people in her unit to learn her true identity, but they are cool with it, anyway. There is also a joke about another woman getting caught and sent back home.
* In ''FanFic/PrettyCurePerfumePreppy'', [[spoiler:Sasaki, when she was in the basketball team masquerading as her brother]].
* ''[[http://ksarchive.com/viewstory.php?sid=415&warning=1 Kindsar's Phenomenon]]'' reimagines [[spoiler:Captain Kirk]] as this trope - whilst he uses male pronouns throughout, has undergone a reasonably substantial amount of surgery, and intends to keep the male body he finds himself in thanks to the GenderBender [[spoiler:until he eventually has to choose between the convenience of the aforementioned body and [[JumpingTheGenderBarrier remaining bonded to Spock, who can't stay flipped without dying horribly and who is biologically incapable of bonding with another male no matter how much he might want to]]]], he also admits to not really identifying as male, and only passed himself off as such because [[spoiler:[[Recap/StarTrekS3E24TurnaboutIntruder women can't become starship captains]]]].

[[folder:Fairy Tales]]
* In [[http://www.mythfolklore.net/andrewlang/076.htm "The Lute Player"]], the queen dresses as a man to get safely to her husband.
* In [[http://www.mythfolklore.net/andrewlang/053.htm "The Girl Who Pretended to be a Boy"]] the youngest daughter of an emperor disguises herself as a boy and rescues a princess.
* The Creator/BrothersGrimm fairy tale "The Twelve Huntsmen" (who are actually a princess and eleven female companions disguised as men).
* Several Italian fairy tales have this, ranging from going to war, saving a prince dressed as a doctor, escaping from villains, or simply because they feel like it / a magic pony told 'em to. Examples: "Fantaghiro the Beautiful", "The Dragon and Enchanted Filly", "The First Sword and the Last Broom", "Wormwood", "The King of Spain and the English Milord", "The Great Narbone", "The Parrot", "The Canary Prince"...
* In "[[http://www.surlalunefairytales.com/authors/aulnoy/1892/bellebelle.html Belle-Belle]]", Belle-Belle disguises herself as a male knight since her father is too old to fight for the king. Belle-Belle is even wooed by the lady-in-waiting Florida, who does not know that she is a woman.
* In "[[http://www.surlalunefairytales.com/facetiousnights/night4_fable1.html Costanza / Costanzo]]", Costanza disguised herself to go into service because she could not get a suitable bridegroom of RoyalBlood, only one of BlueBlood.
* The Icelandic fairy tale "Literature/TheStoryOfKingOdd" is about an elf queen who is forced by the circumstances to pose as a man in the human world.
* In the Middle Eastern fairy tale ''The Story of the King, Hamed bin Bathara, and of the Fearless Girl'', Princess Sherifa is astonished to hear that the king of the neighboring kingdom has banished all women and wants to find out for herself what's happening. Because of the whole "women are banished" thing, she disguises herself as a boy and quickly becomes the king's new best friend. The king starts to get uncomfortable when [[SweetOnPollyOliver he can't figure out why he's attracted to his friend]] and tries a number of tests to see if his friend is secretly a woman. The princess passes each one and the king finally tries to trick her into undressing for a swim at the beach, at which point she jumps into the ocean and swims away. He only figures out she's a woman by seeing that she carved the truth into a door before leaving.
* In ''Literature/TheDiscreetPrincess'', the titular character delivers her newborn nephews to their EvilPrince father while disguised as a doctor treating him after their last encounter.

[[folder:Films -- Animated]]
* In Disney's ''Disney/{{Mulan}}'', Mulan disguises herself as a man by making her hair shorter and wearing a soldier's outfit so that her disabled father won't have to go.
* {{Parodied| Trope}} in ''WesternAnimation/ThePiratesInAnAdventureWithScientists'' with the pirate named Surprisingly Curvaceous Pirate. No-one in the film seems to work this out, despite it being very obvious.
* ''WesternAnimation/TheBreadwinner'' has been compared to ''Disney/{{Mulan}}'' for its use of this trope. Due to the Taliban's [[NoWomansLand strict rules about women]] Parvana has to cut her hair short and wear her dead brother's clothes to go out and take odd jobs to buy food for her family. Later on she meets with an old friend from school named Shauzia who is doing the same thing.

[[folder:Films -- Live-Action]]
* In {{Slapstick}} comedy ''Film/TheKnockout'' (1914), the hero's girl does this to watch him fight in a boxing match, since no women are allowed in the audience.
* ''Film/{{Yellowbeard}}'': Spoofed; one of the ship's officers is named "Mr. Prostitute" and is an obvious woman with a fake mustache.
* The stoning crowd in ''Film/MontyPythonsLifeOfBrian'', which also doubles as RecursiveCrossdressing.
* In ''Film/ShesTheMan'' (a modern-day retelling of Creator/WilliamShakespeare's ''Theatre/TwelfthNight'', mentioned below), the main character disguised herself as a boy so that she could play soccer after the girl's team was canceled.
* ''Film/PiratesOfTheCaribbeanDeadMansChest'': Elizabeth Swann disguises herself as a man to sneak on board a ship. Since she changes on the ship itself, her dress is found by a few of the sailors, which leads to a mad rush to find the stowaway naked lady.
* In the 1984 finnish comedy ''Uuno Film/TurhapuroInTheArmy'', the protagonist's wife takes her husband's place in the finnish army for a short while against her will, with an extremely unconvincing [[WigDressAccent haircut and stubble]]. What really gets her, though, is that no-one noticed a thing...not even while they were bathing.
* Viola in ''Film/ShakespeareInLove'', Shakespeare's LoveInterest, who wants to be an actor. [[HilarityEnsues Hilarity]] [[MistakenForGay and awkward situations]] ensue.
* ''Film/{{Yentl}}'' followed this trope. The main character became a man in order to attend a school in Jewish Talmudic Law, which was forbidden for women at the time. It made for some really weird love triangles. [[note]] It was based on a book by Isaac Bashevis Singer, as listed in the literature section.[[/note]]
* In ''Film/CarryOnJack'', Sally steals Albert Poop-Decker's uniform and takes his place on the frigate Venus, while Albert finds himself pressganged onto the same ship as a common seaman.
* The [[spoiler: runaway Jack]] from ''Film/PitchBlack''.
* The Creator/DisneyChannel movie ''{{Motocrossed}}'' involved a girl posing as her brother to enter a motocross race, after he breaks his leg. What makes this one more ludicrous is that the siblings have the ''same name'' (Andy, short for both Andrea and Andrew).
* This trope is the central plot of ''Film/JustOneOfTheGuys,'' an 80's teen comedy. The main character's brother even asks sarcastically if [[ShoutOut she's trying]][[Film/{{Yentl}} to become a rabbi.]]
* After her rescue from Fogg's Asylum by Anthony in ''Film/SweeneyToddTheDemonBarberOfFleetStreet'', Johanna dresses up like a boy in order to hide from Judge Turpin. [[spoiler:Unfortunately, she almost gets killed by her own father, Sweeney Todd, when he fails to recognize her and takes her for a witness to his final vengeance upon the Judge.]]
* ''Film/ConnieAndCarla'', about two female performers who witness a murder, so they go into hiding by disguising themselves as {{Drag Queen}}s (a spoof of ''Film/SomeLikeItHot'' where two jazz musicians who witness the St. Valentine's Day Massacre go into hiding by joining an all-women's jazz band). In other words, they dressed up as men who dress up as women.
* A similar idea is used in ''Film/VictorVictoria'', merely as a way to break into show business. Victoria's singing is apparently far more appreciated by audiences who think she's a gay female impersonator named Victor. The film makes a point that this takes some doing: Victoria is naturally a coloratura soprano (being played by Creator/JulieAndrews) but has to perform as a contralto so that her voice is deep enough to keep up the illusion.
--> '''Norma:''' ''YOU NO GOOD TWO-TIMING SON OF A BITCH!'' '''''HE'S A WOMAN!'''''
* Happens in the third ''Film/FromDuskTillDawn'' movie.
* The Swedish movie ''Mitt liv som hund'' (''Film/MyLifeAsADog'') is about a 12 year old boy sent to live with relatives in the countryside when his mother contracts tuberculosis. One of his new friends, who is also the top player on the local boys' football team, is actually a girl. Keeping up the charade becomes somewhat difficult when she hits puberty and things start to grow ...
* Common in fairy-tale movies (''Film/{{Dragonslayer}}'', ''Film/TheBrothersGrimm'') as a way to conceal the gender of daughters who might otherwise be fed to dragons, kidnapped by witches, etc.
* In the 1950 British thriller ''Film/TheCloudedYellow'', Jean Simmons cuts her hair and exchanges her dress for trousers in order to pass as "Master Fox". The disguise is never seriously tested, which is just as well as she's [[PaperThinDisguise a remarkably unconvincing boy]].
* There is the 2003 Afghani film, ''Film/{{Osama}}'', the first film to come out of Afghanistan after the overthrow of the Taliban. The film is about a 12-year old girl who disguises herself as a boy in order to earn an income for her family, who are left destitute and with no way of earning an income after the death of her father and uncle. ''Osama'' is an unusually realistic example of the trope.
* In the 1979 basketball comedy ''Film/FastBreak'', D.C. (Harold Sylvester) admits to Coach Greene (Gabe Kaplan) that he has unusual feelings for his (ostensibly male) teammate Swish. In the climactic game, Swish unwraps her breasts and hits the court. D.C. is relieved.
* Princess Leia briefly disguises herself as the bounty hunter Boushh in ''Film/ReturnOfTheJedi'', though this barely counts since he's also an alien.
** And since, at least in the Old Republic, female soldiers weren't a rarity--there are female pilots in Episode I who attack the Trade Federation control ship, not even going into the Expanded Universe or female Jedi.
* ''Film/MaVieEnRose'' introduces such a character (a tomboy who goes by "Chris") right at the end, [[spoiler:right after Ludovic's parents have given in to the DoubleStandard]].
* The Creator/{{Disney}} live-action version of ''Film/SwissFamilyRobinson'' has Roberta (or "Bertie") do this, as she and her grandfather have been captured by pirates. Not very convincing, and TheReveal shows that she's a girl when her head wrap is pulled off to reveal... really short hair, but a suddenly more girlish face.
* The German film ''Film/SchwarzerJagerJohanna'' (1934), in which Marianne Hoppe plays a woman who joins the Black Brunswickers during the Napoleonic Wars to follow her loved one.
* In ''Film/{{Salt}}'', Evelyn Salt disguises herself as a man in order to get into the White House towards the end of the film. Creator/AngelinaJolie makes an eerily convincing man.
* The Canadian Short "No Bikini" shows that bath and this trope '''do''' mix sometimes. Robin, a 7-yr girl, ''hates'' bikinis, but girls must wear a swimsuit for a swimming class. So she pretends to be a boy so she can attend just in swimming trunks.
* The Creator/WhoopiGoldberg vehicle ''Film/TheAssociate'' was a double version; she not only dressed as a man, but went white to win big in business.
* ''Film/TheChallengers'' has a girl dressing up as a boy so she can play in the school band.
* There is a Soviet comedy called ''Film/MyDearlyBelovedDetective'' about [[DistaffCounterpart two female detectives with the last names of Holmes and Watson]]. At one point during an investigation they dress up to sneak into a club of bachelor men. The head of the club gets wind of this and states that all the members will undergo "an embarrassing examination"... which consists of every member being forced to give a gentleman's word he's male. Holmes passes. Watson has some problems, but an admirer takes the blame for her.
* There's another Soviet movie, called ''Film/HussarBallad'', whose protagonist, Shurochka Azarova, is the TropeNamer for this trope in the Russian counterpart of Wiki/TVTropes.
* ''Film/PrincessOfThieves'' centers on Robin Hood's daughter, Gwyn, who dresses up as a man to follow her father.
* In another Robin Hood example, Maid Marian first appears dressed in armor and assumed to be male in ''Film/RobinHoodPrinceOfThieves''.
* Katharine Hepburn takes her turn in ''Film/SylviaScarlett''.
* In ''Film/{{Lockout}}'', Emilie ends up the only woman in the middle of a space prison riot so Snow must disguise her as a prisoner in the hopes that they can sneak past the others. He does this by rubbing coffee, motor oil and dirty toilet water in [[DyeOrDie her hair]]. The other prisoners still take an interest in her for being a "pretty boy" inmate, forcing Snow and Emilie to fight their way through anyway.
* The French film, ''Film/{{Tomboy}}'', has a 10-year-old girl move to a new neighborhood. Throughout the movie, she passes herself off as a boy, even playing soccer without a shirt, kissing another girl, and swimming without a top.
* In ''Film/FrankAndI'', a young girl convincingly (in the movie) pretends to be a boy up until her master makes her drop her pants and beats her with a whip. When he scolds her for crying, she confesses that she's a girl and she loves him.
* In ''Film/ColorOfNight'', [[spoiler:Richie]] turns out to actually be [[spoiler:Rose]] in disguise.
* In ''Film/RobinHood1991'', Marian sneaks out of the castle, cuts her hair and dresses as a man to join Robin and his Merry Men.
* In 1952 swashbuckler ''Sons of the Musketeers'' (aka ''At Sword's Point'') one of the sons is quite obviously a daughter (played by Creator/MaureenOHara), but absolutely nobody notices until after she takes her hat off.

* In ''The Secret of 1798'' Catriona dresses up as a boy so she can go fishing with her father. She simply borrows a neighbour's clothes and hides her hair under a large hat. The ruse is up immediately when the boat capsizes and they are rescued by a French ship.
* In ''The Breadwinner'', a girl named Parvana, who lives in Afghanistan, disguises herself as a boy in order to earn money for her family because her father was arrested and her brother was too young to provide for them.
* In ''Becky'' by Lenore Hart, Becky Thatcher (Tom Sawyer's childhood sweetheart) passes herself off as a man and fights in the Civil War.
* The Creator/HarryTurtledove alternate history novel ''Literature/TheGunsOfTheSouth'' features Molly Bean, a prostitute who disguises her flat-chested self as a man to serve in the Confederate States' unit Castalia Invincibles. She poses as her "cousin" Melvin Bean and joined because the war was taking away all her customers. Ignorant and illiterate, she learns to read and begins to fall for her teacher. How much combat did she see? She was at ''Gettysburg'', y'all. She later serves a surprisingly vital role in defeating the AWB men who are time travelers, by being a popular bedmate while covertly spying on them. Her letters to her lover describe many futuristic marvels (None of which she understands, but her teacher/future husband twigs onto the fact that these guys are from the future). These prompt him to instruct her to go to [[OurPresidentsAreDifferent Confederate President Robert E. Lee]] and describe everything she'd seen. She does, but her attempts to hide her womanly self make it difficult (Lee can't figure out [[CrowningMomentOfFunny why she keeps on mixing up "I" and somebody named Melvin in her story]]). When the CSA goes after AWB, she shows back up in uniform and the commander's reaction ("you still haven't grown a beard?") makes it clear he knew all along about Molly but decided to keep it quiet due to her courage. After she helps take down the AWB, she marries her teacher. In RealLife, there was an actual Molly Bean who enlisted in the Invincibles, but she was discovered and sent home - in February, 1865, more than 2 years after joining the unit. Her livelihood as a prostitute was pure author's invention.
* The Robert A Heinlein novel ''Literature/TunnelInTheSky'' features an example where "Jacqueline Marie Daudet" is mistaken for a young boy (in part due to constantly wearing body armor) by another boy during an advanced survival test on a far away planet. She continues to pretend that she's "Jack Daudet" for weeks, including through some sexist commentary by her survival partner, until the beans are spilled by someone the two of them rescue. For 1955, the premise that girls could do things just as well as men could was pretty advanced.
* This is the main storyline of the historical novel ''Literature/PopeJoan'' (based on what may have been a RealLife example as well, but is generally considered fictitious).
* The old man's granddaughter in ''Literature/SwissFamilyRobinson'' who was disguised as his grandson.
* Creator/TerryPratchett's ''Literature/{{Discworld}}''
** ''Discworld/MonstrousRegiment'' spoofs the everloving hell out of this one. Our heroine Polly Perks joins the army of her war-torn home country of Borogravia, under the alias of "Oliver Perks", to look for her strong-but-simple brother Paul. [[spoiler:Along the way, she discovers everyone in her squad ''except'' the limp-wristed commanding officer, including the boisterous and apparently quite male Sergeant Jackrum, is also a woman disguised as a man, as are quite a few members of the Borogravian top brass]]. Pratchett also plays this for drama as much as for laughs, with Polly becoming disgusted by the contrast between how men and women are treated in Borogravia. What's really ironic is that when the regiment has to [[RecursiveCrossDressing dress as women]] in order to infiltrate an enemy base, the male lieutenant is simply waved through, but Polly is assumed to be a man dressed as a woman and questioned. Even more ironic is when Jackrum states how [[spoiler: so many of the upper brass are women and is then astounded to realize that ''every single one of them'' thought ''she'' was the only one in the army doing this]]. Oh, and the song exists in the setting. She took the name as a reference, but finds the joke gets old when people keep asking if she's heard of it.
** The [[Film/TheAdventuresofPriscillaQueenoftheDesert performing troupe of female impersonators]] in ''Discworld/TheLastContinent'' included an actual female, who was filling in for her brother. And turned sideways because Rincewind honestly doesn't notice, though he did get upset that his (presumably male... ish) Luggage was now dressed in high heels (a lot of them) and a frilly pink tablecloth.
** An obscure Pratchett use of this trope, from the ''Assassins' Guild [[AllThereInTheManual Discworld Diary]]'', reveals that a few Polly Olivers had enrolled in the then all-male Guild school, by means of a short haircut and a note excusing them from gym classes. One former [=SPO=] became head tutor for Black Widow House after the Guild school went co-ed, and now teaches Edged Weaponry and Fencing.
* Alanna of Trebond from the ''[[Literature/TortallUniverse Lioness Quartet]]'' books by Tamora Pierce. As a nine-year old she starts dressing as a boy in order to train for knighthood as [[MeaningfulRename Alan]], and keeps it a secret until after she's already earned her shield (and thus is formally [[SheIsTheKing Sir Alanna]]).
** In one of the short stories set in the same universe, a character is revealed to have disguised herself as a boy and ran away from home because her stepfather wanted her to be veiled like the other females in their country and was going to arrange a marriage for her.
* Dernhelm/(Éowyn) from ''Literature/TheLordOfTheRings'' is a classic example. In her Crowning Moment of Awesome, she is able to kill the Lord of the Nazgûl precisely [[NoManOfWomanBorn BECAUSE she is not a man]].
** The Witch-King's belief that no man could kill him came from a prophecy by Glorfindel a thousand years before. The prophecy said "not by the hand of man shall he fall." The Witch-King thought he was invulnerable, but he got shivved by a hobbit (not a Man) and his head struck off by a woman (not a man). Which just goes to show you should always read the fine print.
* In Creator/EdwardEager's ''Literature/HalfMagic'' a young girl gets really annoyed at Lancelot so she wishes that she was his match in strength and skill, then conjures a suit of armor and challenges him to a duel. She wins and the crowd cheers her. When the king asks her to remove her helmet she does so, having forgotten she still looks the same underneath. As the mood of the crowd shifts from shock to anger, she's called names and Lancelot is jeered for being beaten by a girl, for all of five minutes before Merlin erases everyone's memories.
* The main character of [[http://ib-archive.livejournal.com/36322.html this story]] in the Livejournal-based "webzine" ''Imaginary Beasts''.
* In the children's picture book ''Little Kay'' a girl dresses up as a boy to become a knight. The king somehow finds out there's a girl among the men, and asks his advisers how he can figure out which one she is. In an inversion of the Achilles myth, the advisers suggest offering jewels and pretty fabrics and so on, on the assumption that the girl will be the one interested. Since this is a comedy, though, the men all turn out to be raging dandies who ''love'' the gaudy stuff while the girl spurns it. The only one who offers useful advice is the castle maid, who suggests the king have them all drink a toast, since when they all tilt their heads back to drink the men's Adam's apples will be apparent. This proves effective.\\
After the girl is discovered, the sultan is so impressed that he decides to make her a knight anyway, since she is the only one in the army who isn't a complete dandy. Dressed as a boy, she goes off on a quest which will win her the hand of a princess. She rescues the princess, and the princess discovers she is a girl, but they decide to get married anyway.
** Possibly based on a Russian fairy tale - at the end of that story, the king asks the girl to bathe with him, she goes to change... and runs off, leaving a note behind saying "by the way, yes, I AM a girl."
*** There is an Italian tale which has the same scene (except the girl fakes an urgent message forcing her to return home). It seems to have inspired [[http://en.wikipedia.org/wiki/Fantaghir%C3%B2_series an entire film series]]
** There was a similar fairy tale, only that the whole group was a bunch of girls. When they got wind of the 'tests' to expose them, they would try to confuse things even more. When offered jewels and fabrics, some of them ignored them, some of them appraised the valuables, and a couple of them 'stole' some of the gems. When ashes were strewn across the threshold (on the assumption that the girls would try to clean it up), most of them marched right across it, while a few of them tried to clean it up and made the mess worse in the process.
* In ''The Mother-Daughter Book Club'', one character wears a boy's uniform and helmet to try out for the school hockey team, since the coach refuses to let a girl join. Naturally, her skills secure her a slot on the team, even after her identity is revealed.
* In ''The Girl Son'', Imduk, a Korean girl is disguised as a boy so that she can attend school, at a time when it was believed only boys could learn the Chinese language, with the approval and knowledge of the school's principal.
* Rune, from ''Literature/TheLarkAndTheWren'', passes as a boy to join the Bardic Guild, which only accepts men. Somewhat subverted in that she's fairly open about her gender with most people not directly connected to the Guild. [[spoiler:Also, when she gets the apprenticeship and reveals her true gender, she is savagely beaten and both her instruments are broken.]] Considering they were planning to castrate "him" to keep "his" pure voice, this may have been a better fate. It turns out well enough in the end: [[spoiler:She throws in with a group of freelance bards who lack the Guild's prejudices]].
* In ''The Zucchini Warriors'', one of Creator/GordonKorman's Literature/MacdonaldHall books, the star of the Macdonald Hall football team is in fact Cathy Burton from the girls' school across the road, wearing the name of school nerd Elmer Drimsdale (who has to keep up the ruse out of uniform). The resulting fame goes to his head a little.
** [=ZICTORY=]!
* In the third Literature/FinneganZwake novel, Uncle Stoppard's [[ShowWithinAShow novel]] uses this with [[Theatre/{{Hamlet}} Ophelia]]/"Osric". Seriously.
* In the novel ''Literature/TheShakespeareStealer'' a girl disguises herself as a boy so she can be an actor, since it was illegal for women to perform on the Elizabethan stage.
* Exactly the same thing happens in ''No Bed for Bacon'', the novel upon which ''Film/ShakespeareInLove'' was (very) loosely based.
* Creator/EstherFriesner's ''Literature/MajykByHookOrCrook'' and ''Literature/MajykByDesign'' feature a [[OurElvesAreDifferent Welfie]] swashbuckler who prefers to be called "A Blade for Justice". [[spoiler:Blade turns out to be Kendar's wife, Mysti who, whilst hiding a legendary bust and still wearing twinkly stuff on her eyelids, dies in a fight against a dragon because of a combination of the dragon's magical resistance and a poorly timed Disney-esque sword-throwing incident and is brought back to life by a rather stupid prince whom she had no intention of marrying. Both Kendar and Mysti took the "Til death do us part" deal pretty seriously. Hilarity ensues in ''Majyk by Design'' when they hook back up with Mysti still in costume and Kendar's brother and aunts in eavesdropping distance.]]
* Pamela Kaufman's ''[[http://www.amazon.com/Shield-Three-Lions-Pamela-Kaufman/dp/0609809466 Shield of Three Lions]]'' has the main character, a young girl, dressing up as a boy to save herself from being killed off or married for her property. She ends up going off to the Crusades and falling in with [[UsefulNotes/RichardTheLionheart King Richard]]. Among other things, he falls in love with her as a boy and there is much confusion and danger (since he's the king) when he realizes she's a girl.
* ''Literature/BloodyJack'' is a young adult novel about a London orphan girl who joins the Royal Navy as a ship's boy. Risky, but much more attractive than dying of starvation. This causes problems both comedic and poignant when she [[spoiler:falls in love with a fellow ship's boy, thinks she's dying when she gets her period and has nobody to ask about it]], etc. It has several sequels, and the character sometimes reverts to this trope in a pinch, even though by then she's filled out a little more and presumably no longer looks like an androgynous eleven-year-old. People still buy it, though.
* Nearly every character in Creator/PiersAnthony's ''Refugee'' (in the series ''Literature/{{Bio of a Space Tyrant}}'') ends up dressing as a member of the opposite gender as a defense against ubiquitous space pirates.
* In John Barnes's ''Literature/OneForTheMorningGlory'', Calliope dresses as a man. Characters pretend to be deceived. Sometimes even she forgets that she's dressed as a man and glares at people who refer to her as male.
* The main character of Isabel Allende's ''Daughter of Fortune'' goes off to California disguised as a man in order to find the lover who left her to seek his fortune there.
* In''Cue for Treason'', the young runaway Kit, who joins an Elizabethan theatre troupe and proves good at [[RecursiveCrossDressing playing female parts]], is actually called Katherine.
* Buran in Barbara Cohen and Bahija Lovejoy's ''Seven Daughters and Seven Sons'' disguises herself as a boy in order to make her family rich, since her father has no business sense. SweetOnPollyOliver ensues.
* Princess Miriamele in Creator/TadWilliams's ''Literature/MemorySorrowAndThorn'' dresses as a servant boy when she wants to roam the Hayholt unrecognized, making this a cross with KingIncognito. Her disguise is effective enough that the hero, Simon, is fooled (granted that he's not all that observant when it comes to girls), even after they meet in the wilderness. Wiser characters do see through it, though.
* [[spoiler:Briony Eddon]], in the same author's ''Literature/{{Shadowmarch}}'', tries this rather unsuccessfully.
* One of the tales in Creator/{{Boccaccio}}'s ''Literature/{{Decameron}}'' features a daughter of the King of England traveling to Italy disguised as an abbot. She falls in love with a young fellow she meets on the way, but he is [[MistakenForGay quite disturbed]] by her advances until she places his hand on her chest.
* In ''One Corpse Too Many'', the second Literature/BrotherCadfael mystery by Creator/EllisPeters, Godith Adeny (daughter of Fulk Adeny, foe of King Stephen of England) does this by dressing like a novice monk to prevent capture by the king, which would have caused her to be held for ransom. Cadfael deduces who she is quite quickly in the book. In [[Series/{{Cadfael}} the TV show of the book]], he sees through her disguise instantly. As does the audience.
** In a later novel, done again by "Brother" [[spoiler:Fidelis]], and this time the ruse is successful. Even Cadfael is completely fooled until almost the very end of [[spoiler:the eleventh book, ''An Excellent Mystery'']].
* In Jane Yolen's ''Literature/SwordOfTheRightfulKing,'' [[spoiler:Gawen]] turns out to be [[spoiler:Guenivere]]. Even the narrator is in on the trick, since the sections told from her point of view continue to use masculine pronouns.
* Lampshaded with Blabbermouth in ''Haroun and the Sea of Stories'' by Salman Rushdie. "Don't you know girls have to ''fool people'' every ''day'' of their ''lives'' if they want to get ''anywhere''?" When her secret is revealed, the only character bothered by it is quickly chagrined by someone more awesome who isn't.
* In ''Literature/TheAnubisGates'' by Creator/TimPowers, [[spoiler: Jacky (short for her middle name, Jacqueline. Her real first name is Elizabeth)]] does this in order to infiltrate London's criminal underworld and track down the unnatural creature that killed her fiancee.
* Eponine in ''Literature/LesMiserables'' for a while - she trades outfits (with a boy who is actually described as enjoying crossdressing for a lark) to disguise herself so she can sneak into the barricades. Marius doesn't even recognize her when she [[spoiler: takes a bullet that saves his life and ultimately ends hers]], but that might just be him being a silly, tactless and clueless emo kid.
* Played with in Swedish author Ulf Stark's ''Dårfinkar och dönickar'', in that the crossdressing is initially a mistake - Simone is assumed to be a boy called Simon. She becomes increasingly invested in her disguise as the story progresses, though.
* Another Swedish example is Caroline in Maria Gripe's ''Skugg-/Shadow'' books, who spends large parts of the books pretending to be a young man called Carl. She does it for several reasons: increased freedom, to gain a certain job, and for the sheer heck of it. She will also quite happily flirt with both men and women. (Which backfires when two of them fall deeply in love with her and decide to marry each other, bonding over their mutual love for Carl. Yeah.)
* Joanna Sedley in Creator/RobertLouisStevenson's ''Literature/TheBlackArrow'' may be the least convincing example of this ever. Everyone who sees her realizes that she's a girl, except for the [[TooDumbToLive protagonist]], who thinks his new friend is just really wimpy.
** Stevenson didn't put too much effort into it for two reasons: 1) He was writing it as part of a serial, and having her listed as a boy for the first few installments (it originally appeared in a weekly kids' magazine) would have confused the readers, and 2) he was only writing it for a quick buck while he wrote ''Literature/PrinceOtto''. Ironically, ''The Black Arrow'' ended up being much more popular.
* Arya Stark in ''Literature/ASongOfIceAndFire'' and ''Series/GameOfThrones'' has this trope forced upon her, although she was something of a tomboy in the first place.
** In the first book, her unkempt, [[{{Tomboy}} tomboyish]] appearance leads to lots of people mistakenly calling her "boy", and she has to correct them so often that "I'm not a boy" practically becomes her catchphrase. In the second book, once she's in disguise and actually trying to pass off as a common boy, when someone sees her ruse she has to repeat her catchphrase with a twist: [[CrowningMomentOfFunny "I'm not a girl!"]]
** [[ZigzaggingTrope Brienne is an interesting case]] in that she does look like a tall, powerfully built man; she would have a ''harder'' time trying to look feminine than passing as a man. As she's one of the strongest knights in the Seven Kingdoms, she was able to secure a place in [[PraetorianGuard Renly's guard]] without actually needing to hide. The only way you could tell her actual gender is by [[SamusIsAGirl seeing her bareheaded]], which logically leads her to keep her helmet on when she'd rather not be recognized.
** While it hasn't been explicitly revealed as of yet, the half-Summer Islander, slim, smooth-faced Dornish [[SdrawkcabAlias Alleras]] with the widow's peak who's not interested in women bears a striking resemblance to the half-Summer Islander, slim, Dornish female Sarella whose father had a widow's peak.
** Deconstructed with Brave Danny Flint, also the subject of a romantic song, who posed as a boy to join the Nights Watch. Apparently the real 'Danny' Flint was raped and murdered, presumably by her [[ArmyOfThievesAndWhores fellow soldiers]] when her identity was discovered. Just another average day in [[CrapsackWorld Westeros.]]
* Winter Ihernglass, of ''Literature/TheShadowCampaigns'' series, escaped from an OrphanageOfFear by enlisting in the Vordanai army. She's one of the only rankers in the [[ArmyOfThievesAndWhores First Colonials]] who volunteered for service in Khandar, as it was the furthest posting possible from Vordan and the least likely to contain anyone who'd recognize her. The reader is in on her identity from the first chapter, but not anyone else; frequent mention is made of the fact that she would be dishonorably discharged if her true sex became known. (She initially gets away with it by pretending to religious sentiments in order to avoid the other soldiers' brothel and tavern visits. Her RankUp in the beginning of the first book also helps, as [=NCOs=] get private quarters; previously she had purchased her own tent out of pocket to avoid sharing quarters.) Lucky for her, when her CO eventually does find out, he decides to keep up the masquerade, as she's far too competent to let go.
** Winter isn't the only female soldier in the Colonials, either. [[spoiler:Bobby]] is revealed to be female about three-quarters of the way through ''The Thousand Names,'' when she suffers a grievous wound in combat. Her fellow noncoms also decide to keep the secret, although this has more to do with the nature of her survival than her sex. (Hint: she undergoes an EmergencyTransformation that would see her executed for witchcraft back in Vordan.)
* Michelle, the main character in Elaine Moore's ''Get That Girl Out of the Boys' Locker Room'', becomes this trope so she can play on her school's boys' football team.
* Deryn/Dylan in Creator/ScottWesterfeld's novel ''Literature/{{Leviathan}}'' disguises herself as a boy to join the air forces.
* Nastily subverted in ''Iron Dawn'', in the backstory of Barra the Pict: seeking her fortune in the male-dominated Mediterranean, she dresses up as a young man and joins a group of bandits. She need not have bothered, as the thugs were disappointed to discover that she ''wasn't'' a boy when they turned upon and gang-raped her.
* Creator/MarionZimmerBradley's wizard Lythande is a woman who disguised herself to be able to learn magic; by the time her teachers found her out, she had learned too much for them to send her away. Instead, her punishment was that if any man should learn she was a woman, she would lose her powers, thus condemning her to continue the masquerade for the rest of her life.
** In her ''Literature/{{Darkover}}'' novel ''Hawkmistress'' Romilly runs away from home and disguises herself as a boy. She proceeds to fall in love with a man who seems to return her interest. Unfortunately it comes out that he genuinely prefers boys and is enormously taken aback, not to mention turned off, when he discovers she's a girl.
--> "Don't cry, mistress, I swear I won't touch you!"
--> (Romilly cries harder)
* In one of the ''Franchise/StarWars'' novels, Princess Leia debates trying to pass herself off as a man. She takes a good, long look in her mirror, and decides her figure is far too emphatically female. (Probably intended as an ironic reference to her Sweet Polly Oliver turn in ''Film/ReturnOfTheJedi'')
* Kite from ''Literature/SewerGasAndElectric'' acted out this trope during the American Civil War.
* Creator/IainBanks's ''Literature/TheWaspFactory'' adds a twist in that ''the protagonist herself'' isn't aware of this. Yes, it's a weird book.
* In Stephanie Kennedy's 1980s YA novel ''Hey Didi Darling'' this trope is the main plotline. A GirlGroup decides to dress up like boys and form Tommy & The Tigers in order to get gigs.
* Miranda, the title character from ''Literature/{{Maledicte}}'', passes herself off as a young man to get revenge on her lover's father. The male name and pronoun are used even in scenes from "his" point of view, which definitely makes for some odd sex scenes. Actually, the entire book is an odd experience - Maledicte's deception is so complete that the reader forgets that it ''is'' a deception.
* Judith, the teenaged protagonist of the young adult novel ''The Minstrel's Tale'', is forced into an ArrangedMarriage by her stepfather. Not only is she deeply put off by her bridegroom, who is at least thirty years her senior, but on the night of their betrothal dinner she falls in love with the young minstrel who comes to play and sing for them. He leaves her an instrument and a note suggesting another way of life, which she accepts gladly; she cuts off her long hair, dresses in clothes belonging to her deceased brother, and runs away to minstrel school.
* In ''My Father Had a Daughter'', a fictionalized account of the life of Judith Shakespeare, the heroine dresses as a man in order to sneak off to the Globe Theater and act in [[Creator/WilliamShakespeare her father]]'s plays. Works well until he figures out who she really is, but even he has to admit some amusement at the trick. The narrative implies that her ruse was his inspiration for ''Theatre/TwelfthNight'' (see the Theater section below).
* In ''Literature/RoseDaughter'', a retelling of "Literature/BeautyAndTheBeast" by Creator/RobinMcKinley, Beauty's sister Lionheart disguises herself as a boy so she can get a job and help support her father and sisters. This somewhat confuses their new neighbors, who are ''quite sure'' that when the family moved in there were three daughters rather than two daughters and a son, but they shrug it off and go about their lives.
* Another Creator/RobinMcKinley example occurs in ''Literature/TheOutlawsOfSherwood'', when a young woman named Cecily joins Robin's band under the name Cecil. She remains undiscovered for quite a while, which is particularly impressive considering her brother Will is also in the band. And Marian disguises herself as a man for a shorter period in the same book.
* In the final book of ''Literature/TheChroniclesOfPrydain'', Princess Eilonwy dresses as a man so she can go off to war with Taran and the others. Something of a subversion, since she fools absolutely nobody who knows her, but they sort of roll their eyes and put up with it because there's really nothing else they ''can'' do at this point. [[spoiler:Besides, if she'd stayed behind like she was told, she would have been killed when Caer Dathyl was sacked.]]
* In the Creator/UrsulaKLeGuin short story "Dragonfly", in the ''Literature/{{Earthsea}}'' setting, Irian dresses as a boy in order to accompany the sorcerer Ivory to Roke, the wizard's school only boys are allowed to attend. Ivory's got his own agenda and [[spoiler:Irian is actually a dragon born in a human body or something, in any case not really a girl, though she doesn't realize that until the end of the story]].
* There's a Spanish-language writer of historic novels, who was a BIG fan of this trope. Almost every novel has a girl impersonating a pageboy, either to follow him to war, to deliver a message, and even so a boy can take her clothes and escape from jail impersonating her.
* ShowWithinAShow example: In ''[[Literature/GarrettPI Gilded Latten Bones]]'', one of Jon Salvation's comic plays used this trope, starring a princess who was raised as a boy and crowned king by her unsuspecting subjects. Apparently this trope hit it off big in [=TunFaire=], as lots of other playwrights immediately stole the idea and wrote their own variations.
* In Creator/PoulAnderson's ''Literature/AMidsummerTempest'', Jennifer dresses as a boy to escape her captors.
* Scyla in ''Literature/ShadowsOfTheApt''
* In ''Sarum'', Aelfgifu dons Saxon armor to fight a skirmish against the Vikings and is initially mistaken for a young man, as she'd intended. Subverted in that her deception never fools anyone for long, but she fights well enough that her brothers insist she be allowed to participate in the Battle of Edington ''without'' having to invoke this trope.
* In Rebecca Reisert's novel ''The Third Witch'', a retelling of ''{{Theatre/Macbeth}}'', the main character Gilly disguises herself as a serving boy to infiltrate Macbeth's castle. He [[spoiler:killed her father to marry her mother, the future Lady Macbeth]]. Gilly has vowed to avenge her loss by killing Macbeth whenever she gets the opportunity.
* In the historical novel ''The Tokaido Road'' (by Lucia St. Clair Robson), the main character Cat travels through feudal Japan dressed in several male disguises. It seems that a lone female traveler would be unusual but not impossible; the real reason for the cross-dressing is to evade a warrant for her arrest.
** In an interesting reversal of the AttractiveBentGender trope, Cat's love interest sees her as an attractive male monk and considers taking "him" to bed. Once the love interest discovers Cat's true identity, he's impressed and has no problem transferring his attraction onto the true female version.
* Alice in Beth Hilgartner's ''A Murder for Her Majesty'' takes this up almost by accident. Having witnessed her father's murder, apparently at the Queen's command, she needs to find a place to hide; conveniently she has a run-in with some helpful boys in the cathedral choir, who think it would be great fun to disguise her as a choirboy.
* In Robin Hobb's ''[[Literature/LiveshipTraders Ship of Magic]]'', after Althea runs away from her family, she asks a friend for advice on how to find work as a sailor on her own merits; the friend snarkily responds that she would have to find a way to be reborn as a boy, preferably one with a different last name. Which is exactly what she does - she disguises herself as a boy, and joins a crew under an assumed name.
* Rosario in ''Literature/TheMonk'', who quickly soon reveals himself to be a woman named Matilda.
* ''Literature/DonQuixote'' plays this trope perfectly straight with Dorotea, a girl who dress as a man who sets to get back her unfaithful lover in the first part of the novel. At the second part, this trope will be parodied and deconstructed
** [[NoNameGiven The daughter of Don Pedro de la Llana]] parodies this trope showing us will use it in RealLife: TheIngenue who has been in a GildedCage all his life and asked his brother to show her the world… that is, the little town they live… at night. She dresses as a man because she wants to hide her identity. [[FridgeLogic But nobody knows her because she had been hidden all her life]]. Justified because she is JustAKid who has lived in a GildedCage and she really doesn’t know better. As Sancho said:
--> "In truth, young lady and gentleman, this has been a very childish affair, and to explain your folly and rashness there was no necessity for all this delay and all these tears and sighs; for if you had said we are so-and-so, and we escaped from our father's house in this way in order to ramble about, out of mere curiosity and with no other object, there would have been an end of the matter, and none of these little sobs and tears and all the rest of it."
** ClingyJealousGirl Claudia Jeronima deconstructs this trope: She is wearing man’s clothes because [[IfICantHaveYou she has murdered a supposedly unfaithful lover]] and Barcelona is having a CivilWar. She wants to conceal her identity so her family would not be harmed by {{revenge}}.
** TheExile Ana Felix deconstructs this trope: Fleeing for Spain for having muslim fathers, she enters Algiers, where the King blackmails her to steal his family treasure hidden in Spain. So she wears man’s clothes to come back with the King’s soldiers and mislead the Spanish authorities. She is captured by them and threatened with execution when she declares she is a woman:
--> [[LampshadeHanging "A woman and a Christian, in such a dress and in such circumstances! It is more marvellous than credible,"]] said the viceroy.
* Ruth Mallory in ''Literature/SomeoneElsesWar''. She doesn't get the idea until someone else mentions it, however, and [[SexSlave wishes she had thought of it]] [[TearJerker much sooner.]]
* Kim from ''Literature/MairelonTheMagician'' hides herself as a boy; she's a street kid, and, being a girl, would be put in a brothel pretty quickly if she was revealed.
* In Creator/EDBaker's ''Literature/TheWideAwakePrincess'', Annie starts her search like this. Once she joins Liam, she readopts a dress.
* In Creator/AndreNorton's ''Literature/IceCrown'', Roane briefly and accidentally does this; her short hair and coverall convince the princess she's male, and when the princess gets a good look at her, she's astounded.
* In Creator/StephanieBurgis's ''[[Literature/KatIncorrigible A Most Improper Magick]]'', Kat tries to run away as a boy to cause a scandal. She doesn't even make it out of the garden.
* A thirteenth century French [[KingArthur Arthurian Romance]] is arguably one of the earliest feminist texts. A woman, Eufeme ("Alas, woman!") gives birth to a daughter, Eufemie ("Alas, girl"; or, "euphemism", a way of speaking around the subject), without a father, and decides to raise her as a son, named Silence ("Seriously, could the metaphor be more clear?"). She becomes famed as a minstrel and a knight, captures Merlin, and is unmasked.
* Tavia from the ''[[Literature/JohnCarterOfMars Barsoom]]''-novel ''A Fighting Man of Mars''; she dresses like a man to escape slavery and the harem of Tul Axtar. She can also fight much better than most women in the Barsoom-series.
* [[spoiler: Brady]] in ''Literature/MrBlank'' and [[Literature/GetBlank the sequel]] dresses as a man to facilitate her multiple allegiances in various conspiracies.
* ''Franchise/DoctorWhoExpandedUniverse'':
** Literature/BerniceSummerfield does it twice:
*** In ''[[Recap/DoctorWhoNewAdventuresAllConsumingFire All-Consuming Fire]]'' by Andy Lane, she disguises herself as a man while undercover in 19th century India. Once the Doctor [[DidYouGetANewHaircut finally notices]], she explains she abandoned her original cover (as a woman looking for a husband) after she decked a man in a pub, and decided she'd draw less attention this way.
*** In the Creator/WilliamShakespeare pastiche "The Trials of Tara" by Creator/PaulCornell in ''Decalog 2: Lost Property'', she's disguised as Bertrand, and inadvertantly becomes one of Queen Strella's suitors. Strella doesn't realise, but her servant Miranda does:
---->'''Strella''': What say you, maid?
---->'''Miranda''': Yes, I say a maid.
---->Have you been out of marriage too long?
:::Later, the Doctor arranges for the three suitors to join a troupe of female actresses as part of the EngagementChallenge, letting Benny engage in some RecursiveCrossdressing. The spectators conclude that Bertrand makes "a twee and awkward girl".
** Deconstructed in the Literature/DoctorWhoMissingAdventures novel ''The Plotters'', where the Doctor's insistence on dressing Vicki up as a boy leads to her being sexually predated upon by a king with a [[PaedoHunt fetish for young boys]].
** The Missing Adventures novel ''The Ghosts of N-Space'' did a similar thing - Sarah Jane dresses as a boy for her own safety in the Middle Ages, and is repeatedly assumed by the other characters to be the Doctor's "catamite", much to her [[{{Squick}} upset]].
* In the short story ''Yentl the Yeshiva Bocher'' by IsaacBashevisSinger, the book which Barbara Streisand's famous movie was based on, Yentl dresses up as a man so that she can study Talmud at yeshiva, an activity restricted to men at the time. She falls in love with a guy (Avigdor) who thinks she's male, while a girl (Hadass) who the guy (Avigdor) is in love with falls in love with her (Yentl). One of a rare small number of circular love triangles. Unlike in the movie, Yentl does not get a happy ending. She is exiled from the town and spends the rest of her life wandering around dressed as a boy, trying to study wherever people haven't heard of her. [[RealityEnsues That's what actually would have happened, seeing as in America women couldn't study Talmud either.]]
* The ''Mémoires du général Thiébault'' mention a girl known as M. de Marbitzky, a German nobleman's natural daughter who dressed as a man (and is referred to with male pronouns in Thiébault's narration). Unfortunately, there are no details about him and the reasons why he lived as a man.
* In "The Misadventures of Maude March", the title character and her sister Sallie disguise themselves as men while Maude is on the run from several crimes, [[spoiler: including murdering a man(which was actually her sister by accident)]]. All the women, and the occasional man with a sister who did that, see through it, though most men are completely fooled.
** In the sequel, "Maude March on the Run!" they are forced to do this again [[spoiler: when Maude is recognized and Sallie has to break her out of prison]]. Again, the trick only works on most men, because women apparently have a sixth sense for this thing.
* ''Literature/AllMenOfGenius'' is about a woman who wants to attend a prestigious scientific academy which only accepts men, and who impersonates her brother to get there.
* In ''Literature/TheFolkKeeper'', Corinna disguised herself as a boy named Corin to become a Keeper, since girls aren't usually allowed to take the position.
* Creator/GeorgetteHeyer has several examples:
** In ''These Old Shades'' the street urchin "Leon" whom the Duke of Avon buys to be his page turns out to be "Leonie" halfway through the book, [[spoiler: though it turns out Avon knew it all along. He's like that.]]
** In ''The Corinthian'', heroine Penelope ("Pen") Creed disguises herself as a boy to run away from home and seek out her childhood sweetheart. Hero Sir Richard Wyndham penetrates the disguise almost immediately, but goes along with it when he accompanies Pen. He advises her to tell people she's named Penn "after the Great Quaker."
** ''The Masqueraders'' has an outstanding example in that not only is heroine Prudence disguised as "Peter Merriot", but her brother Robin [[DisguisedInDrag poses as "Kate Merriot"]]. The book being set in 1746 or thereabouts makes this a bit more believable than it would be in the Regency period.
* In ''Literature/FromAHighTower'', Giselle Schnittel temporarily pretends to be a man named Gunther von Weber in order to enter sharpshooting contests and win money to provide for herself.
* Shallan from Creator/BrandonSanderson's ''Literature/TheStormlightArchive'' successfully uses a boy's or a man's disguise several times in order to gather information or pass unnoticed through war camps. Nobody ever notices, but then she is a mistress of illusion.
* ''Literature/HopeLeslie'' has [[spoiler:Roslin, aka Rosa]].
* UnderAPaintedSky: Samantha and Annamae run away by posing as boys and taking the Oregon Trail west.
* In the ''Literature/TalesOfTheFox'' series, BoisterousBruiser Van's daughter becomes a SweetPollyOliver--Van is horrified at her "unwomanly" desire to fight, while the normally tricky Fox is dismayed at how easily he was fooled by a false beard and deepened voice.
* ''Literature/QueenOfTheTearling'' has an unusual example; Kelsea swaps clothes with one of the male guards who accompany her. The loyal guards know that she is a woman, and the disguise is not meant to be very convincing, it is only to distract the enemies, who are looking for the Queen and are unlikely to get very close.
* In ''Literature/TheArtushof'' Berklinger tries to avoid his daughter getting married by dressing her up as his son instead.
* In ''Literature/TheGoblinEmperor'', Maia has an aunt who disguised as man and became a pirate captain. She is also married to a woman. There is also an aversion, with [[spoiler: Kiru Athmaza]] whom her boss tried to pass off as male to fill a prestigious position at court as no suitable male candidates were available. Maia sees through it ''immediately'', and it is lampshaded both with her saying "I told you he'd notice" and Maia noting her voice is much too high to be mistaken for male. [[spoiler: Maia being Maia, he gives her the job anyway.]] It is possible the disguise failed partly because she was ^not^ crossdressing; the uniform she wears for her job is implied to be the same for women and men.
* Spoofed in ''Literature/KatIncorrigible''; Kat disguises as boy and wants to run away to London. She gets as far as the front door of her house.
* Le'Lorinel from ''Literature/PathsOfDarkness'' is actually a female elf, dressing up as a male. She mostly uses this disguise in order to deflect attention from the fact that she is in fact [[spoiler: Ellifain, the young elf child that Drizzt rescued in ''Literature/TheDarkElfTrilogy'']].
* In ''Literature/TheWitchlands'', Merik initially thinks that Cam is a girl who masquerades as a boy so that she could enlist in the Navy. [[spoiler:Turns out not to be the case, as Cam's a transgender boy.]]
* [[spoiler: Irene Adler]] successfully tricks Franchise/SherlockHolmes in the short story "A Scandal in Bohemia".
* InvertedTrope in ''The Galaxy Game'' by Karen Lord: Conventional wisdom has it that only a woman can be a corporate nexus (the power brokers of Punartam's highly complex social economy), so one character who was born a boy but had a clear talent for it was raised female. From what she says, it's possible she's had surgery, but she doesn't appear to identify as female, exactly, so much as identify so strongly as a nexus that she'll be whatever gender makes that happen.
* The ''Literature/SignalAirship'' series' protagonist, Josette Dupre, used to be one of these before the Garnian military allowed women to serve in a (limited) military role.

[[folder:Live Action TV]]
* ''Series/{{Farscape}}'' did this in the episode "Coup By Clam," when Moya was orbiting a planet notorious for its torturously sexist laws. When a tech was sent over to help, everyone assumed he was male, but Chiana was never convinced and eventually forces a GenderReveal. As Chiana herself put it "I know a male when I see one." Unfortunately, the tech's boss wasn't so understanding, and came within inches of killing her before [[MagnificentBastard Scorpius]] [[NeckSnap intervened.]]
* Spoofed by the character of 'Bob' in the various ''Series/BlackAdder'' series.
** Queenie makes a very poor attempt at this (wearing a big cloak over her elaborate dress) in an attempt to join in on the boys' drinking party.
** Also used for a bit of subtle CharacterDevelopment; in the second series (set in Elizabethan England), when 'Bob' first shows up, Lord Blackadder is both taken in by Bob's disguise and highly attracted to 'him', prompting something of a crisis of sexuality. In the fourth series (set during the First World War), 'Bob' shows up again... and Captain Blackadder's not fooled for a second. Unfortunately, his superior officer ''is''...
** In the same episode, Baldrick attempts an inversion where he disguises himself as a woman to try and seduce the General to marry him for his wealth ([[ItMakesSenseInContext yeah...]]). Blackadder scuttles the plan by pointing out that the General is unlikely to be attracted to a "two-legged badger wrapped in a curtain".
* ''Series/MendolIkemen'': Three girls pose as male idols.
* In ''Franchise/StarTrek'', Ferengi society is highly sexist, and female Ferengi are [[ArsonMurderAndJaywalking denied the right to work, do business, or even wear clothes]]; naturally, in one episode of ''Series/StarTrekDeepSpaceNine'', the plot revolves around a crossdressing Ferengi woman.
** And in another, Quark not only crossdresses but ''[[GenderBender actually gets a sex-change]]'' in order to ''seduce'' a businessman into supporting female enfranchisement. {{Squick}}, squick, squick.
** Quick note about the Ferengi: To them, not doing business is more sexist than not wearing clothes. Their hat is capitalism, after all.
* In the 2006 ''Series/RobinHood'' a Saracen woman called Saffiya disguises herself as a boy called Djaq. It takes the Sheriff of Nottingham several episodes to guess she's a woman and (season 2 spoiler) [[spoiler: he still hasn't pegged that "The Nightwatchman" is in fact Marian in disguise, despite the fact that the masked thief has rather conspicuous breasts]].
* Another RobinHood variation; in the 1991 TV movie ''Robin Hood'' with Patrick Bergin in the lead role, Maid Marian (Creator/UmaThurman) attempts to escape an ArrangedMarriage to the evil Sir Miles Folcanet by disguising herself as a boy and joining Robin's merry men. When the Sheriff of Nottingham attempts to lure Robin into a trap by having his lover impersonate Marian, Marian is forced to reveal herself to Robin to save him. She was more successful at impersonating a guy than the above example, partly because Uma's fairly tall.
* An episode of ''Series/{{Sonny With A Chance}}'' has Sonny disguise herself as a male fan of herself.
* A subversion comes in a ''Series/ChicagoHope'' episode where at the start we see a teenage girl hack off her hair and attempt to pass as a boy on the streets. The subversion comes with TheReveal that the girl is actually a boy that was simply raised as a girl after a botched circumcision.
* In the '90s Fred Savage sitcom ''Working'', Chris Grant (short for Christina) shows up for an interview to join the office where the show is set. The boss is a known philanderer and "good old boy," so Christina dresses and acts masculine to get on the boss's good side and score the job. HilarityEnsues when her gender is revealed to the main character (but not the boss), and then they all hang out in a sauna. Even more HilarityEnsues after Chris is found out, gets fired, and the office rises up against the boss's unfair hiring practices. In the next round of interviews, he's forced to consider females for the job. The woman he chooses to hire is actually the main character in drag.
* Dee in the ''Series/ItsAlwaysSunnyInPhiladelphia'' episode "The Gang Gets Invincible".
** This being ''It's Always Sunny'', and Dee being... Dee, as soon as she takes off her disguise, she breaks her foot while trying to kick a football.
* Many KoreanDrama's ''love'' this trope:
** ''Series/TheFirstShopOfCoffeePrince'' has this trope as its main plot.
** Korean drama (and a Japanese remake) ''Manga/HanaKimi'', with a girl pretending to be a boy to go to an all-boy's school to meet the high jumper she has always admired. Of course, [[spoiler: as a twist, he figured out she was a girl by the first/second episode but purposely didn't tell her that he knew.]]
** Also the heroine in the Korean drama ''Series/ThePainterOfTheWind''.
** The titular heroine of the Korean drama ''Series/QueenSeondeok''.
** In yet another Korean drama, ''Series/HanGukYoung'', Sujeolnyeo Seo-ssi (Lee Tae Ran) dresses like a man and goes out spying at night.
** ''Series/YouAreBeautiful'' has the heroine pretending to be her teenage heartthrob brother in order to take his place in a boy band. Jeremy's reaction to her reveal is priceless.
* Amusingly subverted in ''The Curse of the Claw'' episode of ''Series/RippingYarns'' (a parody of "The Monkey's Paw") with a character who appears to be an obvious Sweet Polly Oliver because her strict Victorian upbringing was so strictly Victorian she doesn't know she's a woman (or indeed what women even are.) The hero is happy to "enlighten" her.
* In the second season of ''Series/TwinPeaks'', [[spoiler:Catherine Martell, presumed dead, disguises herself as Japanese investor Mr. Tojamura. Her costume fools the other Twin Peaks residents, including her husband]].
* In the Chilean SoapOpera ''Series/PampaIlusion'', the female lead is [[HospitalHottie a young and beautiful doctor]] who wants to get close to her misogynistic JerkAss of a father, who disinherited her and her MissingMom when she was born. To do so without being found out, she crossdresses as a male physician, and unwittingly attracts [[SweetOnPollyOliver men]] (like the male lead, who is her dad's business counselor) and [[StupidSexyFlanders women]] (like the old man's house maid)
* Brazilian miniseries ''Series/CopasDeMel'' had a woman disguising as a man to travel with the Brazilian team for the 1958 UsefulNotes/FIFAWorldCup. On renaming, she decides to use the same nickname as her actual, Mel - from Amelia to Melchiades.
* ''Series/TheYoungRiders'': Pony Express rider Lou was really Louise, and managed to keep her real gender hidden from most of the main characters for nearly the entire first season (and from some of them for even longer.)
** Her love interest, [[spoiler: and eventual husband in the series finale]] Kid, learns her secret in the very first episode and agrees to help her keep it. (It's the shared secret that helps them bond together). [[spoiler: The other riders learn it in the fourth episode, but only when they encounter Lou's father and siblings. Teaspoon learns it in the second episodes of the second season.]]
*** Note that the RealLife Pony Express specifically recruited "small wiry fellows, preferably orphans" as riders, making this entirely possible.
* On the first episode of ''Series/TheSuiteLifeOnDeck,'' Bailey disguises herself as a boy to get into Seven Seas High. PlayedWith: The program accepts both genders, but by the time Bailey applied they were out of spots for girls. Fortunately for her, [[LovableLibby London]] created a vacancy by bribing her roommate to quit the program, so Bailey became her new roommate instead.
* In ''Series/DaddysDaughters'', Eugenia (Creator/DaryaMelnikova) disguises herself as a boy to help the school win a football match in Episode 35. It helps she was a UsefulNotes/{{Pettanko}} {{Bifauxnen}} early in the show's run.
* Tom, Leo's fellow apprentice in ''Series/{{Leonardo}}'', is a girl who disguised herself as a boy to escape an arranged marriage and because in Renaissance Florence girls can only paint as a hobby. Her real name is Lisa, which given the series' InThePastEveryoneWillBeFamous tendencies, presumably makes her [[MonaLisaSmile Lisa del Giocondo]]. (This is confirmed in Episode 8.)
* Jacqueline, alias Jacques, a woman disguised as a man while on the run for murder, in ''Series/YoungBlades''. Although in her case, it's a PaperThinDisguise.
* The Disney made-for-TV movie ''Motocrossed'' does this when Andrea Carson must fill in for her injured brother Andrew Carson in a motorbike race. They get away with it because of their similar names; she signs up as "Andy", and while the other racers are male, [[AintNoRule the form doesn't require a gender]].
* In the DarkestAfrica sketch in episode 29 of ''Series/MontyPythonsFlyingCircus'', the explorer called Brian is obviously Carol Cleveland disguised as a man, though no special attention is drawn to it.
* One ''ABC Afterschool Special'' was about a girl who pretended to be a boy because she wanted to play the title role in Theatre/{{Oliver}} and the director refused to let girls try out for the part.
* ''Series/ColdCase'' had that 2-part BootCampEpisode about a girl who joined a military school to prove she can hack it with the best of them. She only found later that her classmates didn't like not because she was a girl but because she was a "barracks rat", a anti-social loner. Only when she softens do they warm to her. She gets killed [[spoiler:by another jealous barracks rat]]
* In William Hartnell-era ''Series/DoctorWho'', the Doctor would often dress up his female companions in men's clothes out of concern for their safety:
** In "The Crusades", the Doctor insists on dressing Vicki up as a boy because he feels this will make her safer in the Middle Ages. Vicki tries her best and the disguise works well, but eventually complains to the Doctor that she's fed up with being a boy and wants to be a girl again. She spends the rest of the story in a [[GorgeousPeriodDress stunning and very feminine]] medieval gown and headdress, which she seems a lot more comfortable with.
** In the later Hartnell story "The Smugglers", Polly is dressed fashionably for the 1960s in trousers and a cap. When she goes back in time to pirate Cornwall, the locals mistake her for a boy, which she admits to the Doctor makes her feel 'very odd'. The Doctor tells her it's better she go along with it for her own safety, as pirates do not tend to be kind to women.
** In "The Woman Who Lived," Ashildr disguises herself as a highwayman. A {{Flashback}} to the Hundred Years War also reveals that she BoundAndGagged a male soldier and [[MuggedForDisguise stole his weapons and uniform]] in order to join the fight.
* ''Series/GameOfThrones'': Arya Stark is disguised as a boy by Yoren to hide from everyone and be taken to the north to safety due to her status of being branded the daughter of a "traitor". After a while, RealityEnsues and it becomes a SubvertedTrope: Arya is only able to conceal her gender from truly stupid people, while anyone with a working brain (Gendry, Tywin, Jaqen, The Hound) sees past the disguise at first glance. By the third season, she's more grown up and it's pretty obvious to people that she's a girl. Before her disguise, there's something of a minor running gag in her doing this ''unintentionally''. She dons pants while practicing with her sword, and people who encounter her during these moments often mistake her for a boy much to her frustration.
* In ''Series/{{Zoey 101}}'', Lola dresses up as ''Steve'' to prove the boys that there's no biological reason they can't act normal when there is a girl around.
* Played for laughs in an episode of ''Series/FamilyMatters''. Laura is buying her first car and sees one she likes, but the sexist salesman doesn't take her negotiations seriously. She disguises herself as a boy by borrowing Eddie's clothes (very baggy on her due to her brother's height), a baseball cap to hide her hair, and of course putting on a deep thuggish voice, and goes back to him to do business. The salesman isn't fooled and rips her hat off, at which point she becomes ''super''-feminine and pretends to cry until he lowers the price.
* In the ''Series/MurdochMysteries'' episode "Shipwreck" this turns out to be the BigSecret of a priest suspected of murder.
** A season 3 episode, "Victor Victorian" featured a whole group of women masquerading as men.
* ''Series/MissFishersMurderMysteries'': The VictimOfTheWeek in "Murder and the Maiden" is a nurse who has adopted the identity of an institutionalized RAAF officer in order to fly.
* In UK children's TV series ''Sir Gadabout (The Worst Knight in the Land)'' the incompetent Knights of the Round Table are regularly saved by taciturn "Sir Knight", who unknown to them, is King Arthur's young daughter, Princess Elenora (Tamsin Egerton), wearing chainmail.
* ''[[Series/CarryOnLaughing Carry On Laughing!]]'': In "The Baron Outlook", French knight Sir Gaston de Lyon, about to be captured by the English, swaps clothes with his mistress Marie, who then pretends to be him. Sir Gaston does get a [[AManIsAlwaysEager little excitable]] [[SexyDiscretionShot in the process]], however.

* ''Manhwa/LoveInTheMask'': Hyu-Bin is essentially forced into being a boy in order to be an effective bodyguard for a wealthy girl the same age. While BodyguardCrush does no ensue, [[EvenTheGuysWantHim even the guys]] [[SweetOnPollyOliver think "he's" pretty]].
* ''Manhwa/HesDedicatedToRoses'': The heroine is a very plain girl who becomes a very [[{{bishounen}} pretty boy]] in order to escape her RichBitch "owner". Somehow no one notices her huge stash of [[UnlimitedWardrobe stylish male clothes]] despite her being a servant.
* ''Manhwa/BoyOfTheFemaleWolf'': The HotBlooded heroine ditched her femininity (except for the part that likes guys) after her mom left her to marry someone else and she [[HeManWomanHater has despised female "weakness"]] ever since.

* In the Music/ManMan song "Poor Jackie", the title character is a killer on the loose who disguises herself as a man to evade the police.
* The Music/GratefulDead song "Jack-A-Roe":
-->Jackie's gone a-sailing with trouble on his mind
-->He's left his native country, and his darling girl behind
-->Oh, his darling girl behind
-->She went down to a tailor's shop and dressed in mens' array
-->She climbed on board a vessel to convey herself away
-->Oh, to convey herself away.
* The Music/HoneyWorks song "[=Love@Liar=]" follows a young girl, inspired by the sound she heard of a particular band, disguising herself as a boy in order to join it and pursue a music career.

[[folder: Mythology & Folklore]]
* OlderThanPrint: Earlier than the TropeNamer is the Chinese legend of [[http://en.wikipedia.org/wiki/Hua_Mulan Hua Mulan]], a woman who joined the army as a man in lieu of her father, which has been made into a [[Franchise/DisneyAnimatedCanon Disney movie]], ''Disney/{{Mulan}}''. This story was first recorded in the 6th century C.E. (The Chinese government has confirmed in recent years that she was, in fact, based on a real person who did indeed serve in the army.)
* Hervor the Elder from ''Literature/TheSagaOfHervorAndHeidrek'' dresses as a man and calls herself Hervard to join a group of vikings, later becoming their leader. It's not until after she has led the vikings, recovered her [[AncestralWeapon father's sword]] and ventured into a land ruled by giants that anyone works out that she is a woman.
* The medieval legend of [[https://en.wikipedia.org/wiki/Pope_Joan Pope Joan]], supposedly a woman who disguised herself as a man to enter the Catholic priesthood and rose high enough to become Pope. Allegedly she was discovered when she went into labour during a religious occasion, and either died in childbirth or was executed for her masquerade. It was widely believed to be true for centuries, even by figures within the Church.
* Another old but non-military Chinese example, the Butterfly Lovers: Zhu Yingtai, who disguised herself as a man to become a scholar. She fell in love with her slightly clueless roommate Liang Shanbo and arranged to have him marry her 'sister.' This does not go as planned.
* The most commonly accepted explanation for the name of Petit Jean Mountain in Arkansas is that a young French lass dressed as a cabin boy ("Little John") to be near her fiance, who was a sailor on a ship headed to the New World. She caught ill and died, and her alleged grave can still be seen on the mountain.
* OlderThanFeudalism: In the fourth century b.C. married women were forbidden to watch the Olympic Games so a woman called Kallipateira dressed as a male trainer to go and watch his/her son compete. It is said that this episode was what started the tradition for both trainers and athletes to attend the games naked.


* Roleplay/DinoAttackRPG has a strange case in that while this trope is played straight, it is not for the usual reasons, as the Dino Attack Team is clearly established to have no objection to hiring women. Instead we have Agent Pyro (who despite spending most of his time wearing a gas mask was clearly stated to be male) [[SamusIsAGirl seemingly turning out to be a woman]]. It is later revealed that [[spoiler: the woman who was unmasked was actually Pyro's estranged daughter, who had stolen his gear while he was passed out drunk and then impersonated him in order to protect him from TheMole that was killing his teammates]].

[[folder:Tabletop Games]]

* In ''TabletopGame/{{Traveller}}'', both the Aslan and the Sword Worlders have specific rules for this. In both these cases this is not a disguise so much as a formalized way to allow vocational flexibility in females without hurting the traditions. In the case of the Aslan it comes about when there are no male heirs and a female has to "become male"; which includes not only carrying out [[ARealManIsAKiller male roles]] but vowing celibacy. In the Sword Worlds it is a way for eccentric women who actually want to go adventuring to do so without hurting the StayInTheKitchen principle.
* Since only men can be knights in the default setting for ''TabletopGame/{{Pendragon}}'', the game suggests this option for players who want to play female characters and whose Gamemasters are not willing to house-rule it.


* Creator/WilliamShakespeare ''loved'' this trope. Partly because, since female actors were forbidden on the Elizabethan stage, [[RecursiveCrossdressing all the young women in his stories would have been played by boys]], and having them dress as boys would make it easier for everyone involved--and add to the layers of sexual confusion onstage (after women were allowed to act on the English stage in the 1660s, playwrights continued to include this as part of the plot as a form of FanService).
** ''Theatre/TwoGentlemenOfVerona'' is the first appearance of the trope in Shakespeare (since sadly he had chosen to leave his [[Theatre/HenryVIPart1 Joan of Arc]] out of drag). Julia disguises herself as a page and follows her beloved Proteus to Milan, helping him rescue Silvia from a band of brigands.
** In ''Theatre/TheMerchantOfVenice'', [[MaidAndMaiden Portia and her handmaid Nerissa]] disguise themselves as a young lawyer and his clerk and follow their new husbands to Venice, where Portia intercedes in the trial of Antonio and saves his life. Portia and Nerissa are likely inspired by their friend Jessica, who earlier in the play disguises herself as a boy to [[ConvertingForLove elope]] with her [[StarCrossedLovers star-crossed lover]] Lorenzo.
** Things get especially interesting in ''Theatre/AsYouLikeIt''. Rosalind is banished by her uncle, and to aid her in her travels she dresses as a young man called [[MeaningfulRename Ganymede]]. Naturally, she runs into the man she secretly loves, Orlando, who is in turn so consumed by his passion for her that he doesn't even recognize her. So Ganymede offers to "cure" Orlando of his love by ''pretending to be Rosalind''. Got that? Male actor playing female character disguised as young man playacting young woman--in love with young man. Complicating matters, a country girl called Phoebe meets Ganymede and promptly [[SweetOnPollyOliver falls in love with "him."]]
** In ''Theatre/TwelfthNight'', HalfIdenticalTwins Viola and Sebastian are separated in a shipwreck. Viola, assuming her brother has drowned, disguises herself as a eunuch and goes into service for Duke Orsino--who decides to send "Cesario" as an emissary of love to the unaccommodating object of his affections, Olivia. [[SweetOnPollyOliver You can guess what happens next.]] And then the actually-not-dead Sebastian shows up and, of course, is promptly mistaken for Cesario. Zany hijinks ensue.
** Imogen of ''Theatre/{{Cymbeline}}'' spends much of her play disguised as a young page, after being framed for adultery and fleeing the royal court.
* Happens fairly regularly in {{Opera}}
** In Beethoven's ''Theatre/{{Fidelio}}'', the title character is actually a woman named Leonore, dressed as a man in order to free her husband Florestan from prison. Awkwardly, TheWarden's daughter is in love with "him."
** Poor Zedenka (''Theatre/{{Arabella}}'', Richard Strauss), forced to dress as a boy because her family cannot afford to let her doll up like her big sister Arabella. She gets her man in the end, so all is well.
** Handel's opera ''Theatre/{{Alcina}}''. Brave girl Bradamante dresses as a man, under the name Ricciardo, to save her lover Ruggiero from the clutches of the sister witches Alcina and Morgana. They ''both'' fall in love with "him." A messy love network ensues.
* The plot comic opera ''The Firefly'' has pretty little street singer Nina run away from home to Bermuda disguised in boy's clothes. Unfortunately, the boy in question happens to be the notorious pickpocket Antonio Columbo.
* The operetta ''Theatre/NaughtyMarietta'' has the title character live disguised as a boy (the son of a puppeteer) to hide from people who are trying to take her back to Naples for an ArrangedMarriage.
* ''Servant Of Two Masters'' has Beatrice, who sometimes wore men's clothing, disguise herself as her brother.
* In Bertolt Brecht's ''Theatre/TheGoodPersonOfSzechwan'', Shen Te has to dress as her fictional (male) cousin Shui Ta, in order to get respect from her clients.

[[folder:Video Games]]
* In ''VideoGame/AssassinsCreedI'' [[spoiler:it's supposed to be a surprise when, after your attempt on Robert's life, a woman takes off the helmet. Might have actually worked if, during the preceding battle, every time "Robert" was hit "he" hadn't sounded like a woman crying out in pain.]]
** If the player has a sufficiently tuned [[SweetOnPollyOliver "babe-dar"]] then the player likely noticed how feminine the target was in the cut scene before the battle even commenced.
** In ''VideoGame/AssassinsCreedIII'' some of the soldiers that wear face covering scarves make grunting sounds that imply this trope.
** ''VideoGame/AssassinsCreedIVBlackFlag'' features Mary Read posing as a teenaged boy[[note]]specifically, William Kidd's fictional bastard son James[[/note]]. While she does a decent job of hiding it[[note]]and ''does'' seemingly fool everyone until she doffs the disguise to instead play a waylaid woman[[/note]], it's pretty noticeable -- for starters, she doesn't have a "''James''" voice -- and the reveal is probably not too much of a surprise, especially if you know your history beforehand.
* Gaol in ''VideoGame/KidIcarusUprising'' dons the Dark Lord armor, which even makes her voice [[EvilSoundsDeep deeper]]. While Magnus already knew her from before, Pit and Palutena are fooled until her armor is broken.
* Faris from ''VideoGame/FinalFantasyV''. Yes, "his" secret [[ItWasHisSled is outed very early on]], but she doesn't start dressing any differently... apart from two or three of her jobs, including the Mystic Knight and the [[BellyDancer Dancer]], both of which only become available after TheReveal. It's also worth noting that she still talks like a man and is clearly uncomfortable the one time she's shown wearing women's clothing.
* A [[GoodBadBug bug]] (maybe?) actually creates one in ''VideoGame/FinalFantasyTactics''. The first stage of the Deep Dungeon/Midlight's Deep occasionally spawns a "male" Time Mage... who [[ScreamsLikeALittleGirl screams like a girl]], literally. If [[HeelFaceTurn Invited]] into your party, you'll discover that she's actually a female unit in everything but in-battle appearance; she can use female-specific equipment and can access the Dancer class (but takes on the appearance of a Bard when she does), and she is susceptible to Steal Heart from male units (and, if taught the ability, can [[SweetOnPollyOliver use the same skill on them]]). She even gets female sprites in the formation menu; just not in battle.
* In the video game ''VideoGame/TheLegendOfZeldaOcarinaOfTime'' Princess Zelda disguises herself as a warrior named "Sheik" to hide from the main villain and help the main hero. The reveal was a big surprise to players when the game first came out, but now it's [[ItWasHisSled so well known]] you can even have her switch back and forth between the two personas in the ''VideoGame/SuperSmashBros'' series.
** On the other hand, people are still trying to discern whether Sheik is male or female; (s)he's almost as confusing as [[VideoGame/SuperMarioBros2 Birdo]]... and the [[Manga/TheLegendOfZelda manga adaptation]] doesn't help matters either.
* ''VideoGame/{{Rhythm Thief|AndTheEmperorsTreasure}}'': [[spoiler: Charlie, though it's never made clear if she intentionally tries to look like a boy [[LadyLooksLikeADude or not.]]]]
* Kaye from ''VideoGame/{{Blazing Souls}}'' is an elven princess who escaped her family and dresses as a man to avoid unwanted attention, working as a bodyguard for Bridgette. [[spoiler:She's caught changing clothes by Zelos of all people, and he's nice enough to keep the secret for her.]]
* [[spoiler:Naoto Shirogane]] of ''VideoGame/{{Persona 4}}''.
** [[spoiler:Also, Izanami is disguised as a male gas station worker.]]
* Despite appearing as an enemy, King was handled as this in the original ''VideoGame/ArtOfFighting'' -- her reason in this case being that due to not being able participate in Muay Thai tournaments as a child due to her gender, she passed herself off as male and continued to do even after moving to the United States. Later games made her femaleness more obvious, even including visible breasts -- although relatively modest-appearing... despite the fact that without binding and concealment, her bust measurement rivaled [[VideoGame/FatalFury Mai]] [[MsFanservice Shiranui's]], which was capitalized on for some fanservicey official art, and occasional in-game fanservice. ''VideoGame/TheKingOfFighters 2001'' threw this muted handling of her appearance completely out the window, but [[FanonDiscontinuity we don't like to talk about it.]]
** In the first game, King's gender was a TomatoSurprise that you could uncover by defeating her with a fireball attack. Too bad her hit cries were so feminine that it hardly counted as a secret.
* Jayle, one of the Einherjar in ''VideoGame/ValkyrieProfile'' is a woman disguised as a male soldier. Interestingly, her commanding officer discovers this, but keeps his mouth shut because they've fallen in love with one another. She's more conspicuously outed just before her death, when a sorceress's seduction spell, fails to entice her. It ''did'' however entice that commanding officer, who runs her through.
** Much like Faris from ''Final Fantasy V'', in battle she continues to dress the same and is acknowledged as her soldier persona for all intents and purposes.
* ''VideoGame/JadeEmpire'' features a theatrical production in a culture where only men may be actors; naturally, if the player character is female, [[AllUpToYou she takes the part anyway]]. Of course, [[RecursiveCrossdressing it's a a female part]]...
* Sypha Belnades in ''VideoGame/CastlevaniaIIIDraculasCurse''. Being a witch, she had to disguise herself to avoid being [[BurnTheWitch burned]]. The game and manual were fairly good about concealing this fact until the very end. Her doppelganger in ''VideoGame/CastlevaniaSymphonyOfTheNight'', however, is feminine right from the get-go. And then ''VideoGame/CastlevaniaJudgment'' [[FanservicePack gives her large breasts and a fanservicey outfit]]. Finally, in ''Pachislot Akumajo Dracula III'', Sypha wears a garb similar to her original look ([[GirlinessUpgrade but with more of an emphasis on her womanly attributes]]) and is frequently seen with her hood down, similar to her zombie doppelganger in ''[=SotN=]'' and ''[[VideoGame/CastlevaniaPortraitOfRuin Portrait of Ruin]]''.
* In ''[[VideoGame/DragonForceSega Dragon Force]]'', one of the leaders is a female who wears intimidating and bulky armor with a face-concealing helmet for the first half of the game. Her proper gender is indicated immediately if you play as her in the campaign, but [[https://archive.is/Pb372 nobody else knows until she takes off the helmet.]]
* In ''VideoGame/RivalSchools'', Akira goes undercover in a body-concealing motorcycle helmet and leather jacket to investigate her older brother's disappearance. This is necessitated by the fact that her brother attends an [[OneGenderSchool all-male school]] for {{delinquents}}.
* In ''VideoGame/FireEmblemAwakening'', [[spoiler:when Lucina comes from the future to save her father in her attempts to stop the BadFuture, she disguises herself with a CoolMask concealing her eyes (which have a Brand that would reveal her identity) and [[CompressedHair tucks her hair]] into to [[BiFauxnen assume a boyish appearance]] and goes by the pseudonym of [[VideoGame/FireEmblemAkaneia "Marth".]] Eventually, she reveals her true gender after her mask is broken while averting an assassination attempt on Chrom.]] It is also suggested that [[spoiler: Lon'qu, a warrior fighting in the tournament at Ragna Ferox, lost to "Marth" because even though [[MasterSwordsman he was the more skilled swordsman]], his [[GenderReveal realization that "Marth" was a woman]] caused him to lose his edge due to his [[DarkAndTroubledPast trauma-induced]] [[CannotTalkToWomen gynophobia]].]]
* A common trope in the early ''Franchise/MetalGear'' (particularly in ''Metal Gear 2: Solid Snake'', ''Metal Gear Solid'', and ''Metal Gear: Ghost Babel'') had Solid Snake having to rendezvous with a female ally who has already infiltrated the enemy by disguising herself as a soldier. Particularly in ''[=MG2=]'' and ''MGS'', the only way to determine who is Snake's contact is to follow said contact to the Ladies' room.
** Or if the player is detail oriented, they may notice that the actually-female soldier sways her hips as she walks, and has slender legs. Snake himself notices it, a fact which is later [[ShoutOut given a nod]] in ''VideoGame/SuperSmashBros Brawl'' when he realizes immediately that SamusIsAGirl.
** In ''VideoGame/{{Metal Gear Solid 2|SonsOfLiberty}}'', Olga Gurlukovich disguises herself as a Cyborg Ninja similar to Gray Fox from the first game, while disguising her voice and using the alias of "Mister X."
* In ''VisualNovel/DaCapo'', [[spoiler: Kanae Kudou is disguised as a boy due to her strict traditional upbringing, mainly that she's not allowed to flirt with boys. So much that she already had to transfer schools once when her identity was found out.]]
* Leucos in the latest ''VideoGame/GloryOfHeracles'' game tries this to escape from authorities, but she doesn't pull it off well, and the game's characters [[NoFourthWall (and even the tutorial)]] [[LampshadeHanging lampshade]] this.
* In the obscure Sierra adventure game ''VideoGame/PeppersAdventuresInTime'', the titular character disguises herself as a boy for about 90% of the game, considering that she time travels to the American Revolution.
* Cocona from ''[[VideoGame/ArTonelicoQogaKnellOfArCiel Ar tonelico III]]'' disguises herself as [[spoiler:Tatsumi]] to avoid being detected as a reyvateil.
* [[spoiler:Shiva]] in the first ''VideoGame/GalaxyAngel'' [[VideoGame/GalaxyAngel game]] is made to crossdress for political reasons.
* Flash game ''Star Wish'' has one. Figure it out.
* In ''VideoGame/{{Genji}}: Dawn of the Samurai'', Otohiko is actually [[spoiler:Lady Shizuka]], despite players never hearing Otohiko's voice and the game continually referring to Otohiko as a "he." She did it to avoid the enemy Heishi's pursuit.
* In ''VideoGame/TearsToTiara2''. At one point the party decides to let themselves be captured by slavers. The girls disguised themselves, with some magical help, so they will be kept on the same ship as the guys.
* In ''VideoGame/FantasyLife'', [[spoiler:Princess Laura]], who is first met in her boy disguise.
* The player character of ''VideoGame/QueenAtArms'' has been raised as a boy and given a boy's name for as long as she can remember, but she knows perfectly well that she's a girl. Her adoptive family did this to conceal her true identity, for very good reasons.
* In ''Videogame/StarWarsTheOldRepublic'', it's revealed at the end of the Imperial Agent storyline that [[spoiler:Hunter, the Agent's ArchEnemy]] is actually a woman wearing a holographic disguise as part of her cover. If you're a male, she'll even claim that she's [[DatingCatwoman fallen for you]], giving you the chance for a LastKiss.
* In ''Franchise/TheElderScrolls'' backstory, Barenziah, [[LostOrphanedRoyalty the future Queen of Morrowind]], ran away from her Imperial loyalist foster family as a teen by disguising herself as a boy. She continued to pose as a boy for some time after in order to avoid detection.

[[folder:Visual Novels]]
* In ''VisualNovel/FateStayNight'', Saber is actually [[spoiler:KingArthur, or rather Artoria Pendragon, who used Merlin's magic to disguise herself as a man.]]
* [[spoiler:Rei Ijuin]] in the original ''VisualNovel/TokimekiMemorial'' because apparently her father wanted a boy.
* ''VisualNovel/PhoenixWrightAceAttorneyDualDestinies'' has [[spoiler: Robin Newman. When she's revealed to be a girl, she keeps switching between a very girlish personality and the boisterous, masculine personality she was using before.]]
* ''VideoGame/ProfessorLaytonVsPhoenixWrightAceAttorney'' has [[spoiler: Jean Greyerl, who lived as a boy to hide the fact that she was a witch.]]
* In ''VisualNovel/DaiGyakutenSaiban 2: Naruhodo Ryunosuke no Kakugo'', [[spoiler:the main character's assistant Susato Mikotoba disguises herself as a male defense attorney to defend Haori Murasame, under the name 'Ryutaro Naruhodo' (registered as such by her father).]]
* In ''VisualNovel/{{Hakuouki}}'' has protagonist Chizuru Yukimura dress as a boy to go looking for her father after he goes missing due to laws that prevented women from traveling alone and to make herself less of a target in Kyoto. After moving in with the Shinsengumi, Chizuru is asked to maintain the disguise to prevent an issue about a woman living in the compound. Key members of the Shinsengumi are informed of the truth early on and others see through the disguise later, but it was passable enough that one of Chizuru's love interests gets ''MistakenForGay''.
* ''[[VisualNovel/ShallWeDateNinjaShadow Shall We Date?: Ninja Shadow]]'' has Saori Shishido, a {{bifauxnen}} PlayerCharacter whose [[DudeLooksLikeALady girly-looking]] [[HalfIdenticalTwins twin brother]] Kaname, is murdered. [[AngstySurvivingTwin She]] then [[DeadPersonImpersonation takes up]] [[MySiblingWillLiveThroughMe his identity]] and rooms in with an all-male VigilanteMan group that her brother was supposed to join (who are [[ExPy totally not]] a ninja version of UsefulNotes/TheShinsengumi), determined to punish his killer ''and'' get help from the Vigilantes for her and Kaname's village, which is going through hard times. Her disguise is actually good enough that the Vigilantes often ask her to [[RecursiveCrossdressing dress up as a girl]] ''because'' they believe she's a girly-looking young man.

[[folder:Web Animation]]
* ''WebAnimation/{{TOME}}'' has an interesting example with [[spoiler: Gamecrazed. Because it's a video game, hypothetically anyone could simply [[CrossPlayer Cross Play]] to pull this off. However, the only character to actually do something similar is SOFDTI (an artificial intelligence), who technically didn't have any gender to begin with (but identifies herself as female). When she creates a digital avatar to play the game herself, Gamecrazed is mistaken for a male by Nylocke and SOFDTI saw no reason to object.]]

[[folder:Web Comics]]
* Spoofed [[http://the-whiteboard.com/autotwb1092.html here]] in ''Webcomic/TheWhiteboard'' by Sandy, in response to a customer insisting on talking to one of the guys at Doc's paintball shop..
* [[http://www.airshipentertainment.com/growfcomic.php?date=20081228 Timothy Peter Hugo Stanley]]. "A few crewmembers are convinced he harbors some deep secret, but... it remains a mystery." Beneath is an obvious picture of a (not-very-Foglioesque) girl.
* Emet from ''Webcomic/WarriorU'' dresses as a boy so that she can learn to become a warrior.
* In ''Webcomic/{{Strays}}'', [[http://www.straysonline.com/2012/01/page-202/ Meela's brother cut her hair so they could pass as brothers, rather than the brother and sister their enemies were looking for. She didn't like it.]]
* {{Subverted}} in ''Webcomic/TwoKinds'' with Natani. She dresses and acts like a guy because part of her soul had to be repaired with a piece of her brother's soul. That included the part about gender identity. As a result, [[{{Transgender}} she honestly identifies as male]] even though she is in a decidedly female body. She keeps her breasts bound and disguises her scent so nobody but a trusted few know the truth.
* In ''Webcomic/{{Storm}}'', Eolill often disguises herself as a man to be taken more seriously as a fighter.
* ''Webcomic/StickyDillyBuns'' has a minor case when Ruby (basically a deconstructed {{Ingenue}}) disguises herself as "Rudy" (basically a joke {{White Gang Banger|s}}), in order to assist with one of Dillon's {{Zany Scheme}}s. It's a short-term effort and not a very convincing disguise (although it fools Ruby's sister during a brief encounter), but it perhaps helps Ruby's confidence, as she claims that some of Rudy [[BecomingTheMask rubs off on herself]].
* In a ''Webcomic/KevinAndKell'' storyline, Kevin's dad is in debt to the Bovine Mob, led by a longhorn bull called "Mr Castrato". At the end of the story the police move in, only to find Castrato's jacket and horns abandoned ... "he" was actually a cow.
* In ''Webcomic/SandraOnTheRocks'', Eloise, as part of a convoluted revenge plot, infiltrates a high school along with her girlfriend Nadine under the guise of two new students. She wasn't happy to find out that Nadine, [[ItAmusedMe for her own amusement]], gave her a male fake identity.

[[folder:Web Original]]
%%* Amber Jarrett in ''Literature/DecadesOfDarkness''
* HugeSchoolgirl Dacey "Dawson" Ashcroft in ''Roleplay/SurvivalOfTheFittest'' pretends to be a guy due to the negative attention she received in her previous school, feeling it easier to get through highschool if everyone believes her to be a man. Luckily, she doesn't look all that feminine, and unlike some of the other female Southridge students lacks large breasts.
* In ''WebVideo/VideoGameConfessions,'' [[Franchise/TheLegendOfZelda Zelda]] often goes around in her Sheik disguise, explaining that she feels more free pretending to be both male and [[KingIncognito a commoner]]. Gets weird when [[DepravedHomosexual Link]] [[TwoPersonLoveTriangle starts hitting on her]] [[SweetOnPollyOliver while she's in disguise]].
* ''Literature/WhateleyUniverse'': As per WordOfGod: [[spoiler:Mr. Magic's]] son [[spoiler:'Artie']] is actually [[spoiler:'Gwen']]. He had an affair and she got pregnant, she broke off the affair out of concern 'about raising a child in the unstable life [he] led'. When he saw his child, "for some reason, possibly involving [[spoiler:Gwen's]] tomboyish appearance, he mistook her for a boy. Seeing how elated he was in having a son, she decided to play along and—for some reason—her mother also went with the charade, both telling [[spoiler:Mr. Magic]] that his daughter was a boy."

[[folder:Western Animation]]
* In ''WesternAnimation/FamilyGuy'', one CutawayGag has Peter Griffin [[https://www.youtube.com/watch?v=UDhF9UvElSo spending fifty years pretending to be a woman]], [[NunTooHoly posing as a nun]], and taking care of orphans at a [[TheMissionary Catholic Mission]]. A French Woman wrote a documentary about it called "Mère Bernadette: {{Transvestite}} Child of God" and it won the [[UsefulNotes/PalmeDOr Palme d'Or at Cannes]] and the Silver Scissors at the Bulgarian Lady-Weiner Festival.
* In the ''WesternAnimation/{{Futurama}}'' episode "War Is the H-Word", Leela disguises herself as a man named "Lee Lemon" in order to join the army. Zapp Brannigan is still attracted to her without seeing through the disguise leading to some... confusing feelings.
-->'''Zapp:''' (after the Leela feminine reveal) I've never been so happy to be beaten by a woman!
* ''WesternAnimation/CloneHigh'': The Joan of Arc clone disguises herself as "John Dark" ("Jeanne d'Arc") to join the hoops team, to give them a fighting chance against their rivals. [[spoiler: The whole thing backfires when Abe hates John, and so in respect of Abe, "he" keeps passing the ball to him, even though "he" could probably score "himself"; so they end up being pummelled again, and don't even ''score'' until the last second of the game... which fortunately helps the principal win a bet.]]
** The whole thing is mocked in a leaked production piece; apparently a future storyline had Joan becoming prom queen. The position of Prom King was given to basketball star John Dark. She ends up awkwardly dancing by herself during the prom royalty dance.
** This is actually [[TruthInTelevision based on her historical actions]], although the real Joan made no secret of her gender and wore male clothing just because it was more practical.
*** Although it's a pretty safe bet that the real-life Joan's army [[ItMakesSenseInContext had no dolphins disguised as people.]]
* ''WesternAnimation/GummiBears'' -- Princess Calla does this to avoid getting a bodyguard. Her father finds out and so is impressed at how formidable she is that he immediately agrees that she doesn't need one.
* In one episode of ''WesternAnimation/TheSimpsons'', Springfield Elementary becomes segregated by gender. Since the girls' school isn't teaching math properly, Lisa disguises herself as a boy in order to join the boys' class.
* ''WesternAnimation/MyLittlePonyFriendshipIsMagic'': In the episode "[[Recap/MyLittlePonyFriendshipIsMagicS6E5GauntletOfFire Gauntlet of Fire]]", dragon princess Ember disguises herself as a male dragon to compete in a [[DeathCourse Death Course]], even faking a deeper voice when forced to talk. However, it is [[DownplayedTrope downplayed]] to an extent, since it's not that female dragons ''weren't'' allowed, but rather that she did not want to be recognized after her [[RebelliousPrincess father explicitly told her not to compete]].
* Sam(antha) in ''WesternAnimation/DannyPhantom'' briefly disguises herself as a boy to trick three female ghosts who have made all the men disappear. Her presence was to get the three to use their powers so Sam's team could counter with their own weapon to restore all the men back.
* By day ''WesternAnimation/{{Cybersix}}'' disguises herself as a male high school teacher.
* Combined with YouGoGirl on ''WesternAnimation/{{Doug}}'' when Patti tries out for the softball team.
* An episode of ''WesternAnimation/JimmyTwoShoes'' had Heloise disguise herself as a boy in order to see a list of "Guy Stuff" that Jimmy and Beezy wouldn't let her see.
* An episode of ''WesternAnimation/TheGrimAdventuresOfBillyAndMandy'' has Mandy disguising herself as a boy calling herself Manfred to help out Billy's baseball team which does poorly, as he wouldn't let her join because he doesn't want a girl on his team despite Mindy leading the team that always beats them. She only wears pants and a baseball cap, but once she takes off the cap he recognizes her and kicks her out only to accept her again when she puts the cap back on (he's pretty stupid).
* ''WesternAnimation/ThePowerpuffGirls'': In "Bubble Boy," after capturing and imprisoning Boomer, the girls disguise Bubbles as Boomer and plant her among the Rowdyruff Boys in order to trick them into getting captured.
* In ''WesternAnimation/TheMummyTheAnimatedSeries,'' Alex's friend Yanit turns out to be a girl. Her family have been Medjai for thousands of years, and she didn't feel like breaking the tradition just because she didn't have a brother.
* ''WesternAnimation/TaleSpin'' has a [[GenderInvertedTrope gender inversion]] - Higher for Hire's business is suffering because its boss is female, so Baloo decides to enter an air scavenger hunt. In order to do so, he needs someone to sponsor him, but only an all-female aviation club will sponsor Higher for Hire, so he disguises himself as a lady.
* In ''WesternAnimation/VoltronLegendaryDefender'', [[spoiler: Pidge turns out to be a girl named Katie Holt, who disguised herself as a boy to continue investigating the disappearance of her father and brother after being banished from the property as Katie.]]

[[folder:Real Life]]
* During the UsefulNotes/AmericanCivilWar, some of the corpses of fallen men were discovered not to have been men at all. At least 240 women are known to have served in the ACW disguised as men, [[http://www.amazon.com/They-Fought-Like-Demons-Soldiers/dp/1400033152/ref=pd_cp_b_1 as you can read about here]] Several maintained their disguises after the war in order to qualify for pensions. It was a lot easier for women to get away with this back in the days before routine physical examinations, since often the only physical standards enlistees had to meet were "upright and breathing". Also, many 18th and 19th century women were relatively small-breasted due to inadequate nutrition, and many figured out the trick of padding out their waists instead of trying to completely eliminate their breasts, which was often helped by ill-fitting uniforms and the sartorial customs of the time, which required several layers of relatively thick and unyielding fabrics and often resulted in people resembling unmade beds.
* Joan of Arc did not disguise herself as a man, but chose to wear men's clothing while fighting for practical reasons.
** In general, armor made this sort of thing easier to pull off for those who, unlike Joan, did pull off a Polly Oliver. [[http://upload.wikimedia.org/wikipedia/commons/3/39/Joan_of_arc_miniature_graded.jpg Compare this picture of Joan]] [[http://1.bp.blogspot.com/-twMDpiYJEDc/UKxwes_S-2I/AAAAAAAAJFI/hlDsBNhYloA/s1600/Edward+Burne-Jones.jpg with this of St. George and the Dragon]]. The armor had a generally androgynous effect.
* Deborah Sampson disguised herself as a man named Robert Shurrleff and served in the Continental Army under General UsefulNotes/GeorgeWashington from 1782 to 1783. She was caught by a doctor after getting shot in the shoulder, and was honorably discharged due to her heroism on the battlefield. Deborah allowed her story to become public and gave lectures about her experiences in war until she died in 1827.
* There are at least 22 documented cases of women serving in the Prussian army during the Napoleonic Wars. They include:
** Eleonore Prohaska (1785-1813), who served as private August Renz in the Lützow Free Corps and only revealed her real identity when she was mortally wounded in the battle of the Goehrde (1813).
** Louise Grafemus (1786-1852, born Esther Manuel), a [[JewishMother converted Jewish mother of two]], who served with some financial backing from Princess Marianne of Prussia as an uhlan during the Wars of Liberation (1813-1815), searching for her husband who, as it turned out, was serving in a Russian unit and was killed before the war ended. Grafemus lost her right hand, was promoted to ''Wachtmeister'' (sergeant-major) and was decorated with an Iron Cross. After the war she moved to St. Petersburg, married a second time, and as the widow Louise Kessenich ran an inn called "The Red Zucchini".
** Friederike Krüger (1789-1848) alias August Lübeck served in the Kolberg Infantry Regiment from 1813 to 1815, rose to ''Unteroffizier'' (sergeant), and was awarded an Iron Cross and a (Russian) Cross of St. George after being wounded and discovered to be a woman at the battle of Dennewitz in 1813. After the 1815 campaign she retired from the military, married another ''Unteroffizier'', and had four children.
** Maria Werder, the wife of a landed gentleman, served as a hussar to be with her husband in the campaigns of 1806/7 and 1813. She was promoted to ''Wachtmeister'' in the 2nd Silesian Hussars and and revealed her real identity only when she left the army after her husband was killed in the battle of Leipzig.
* Thérèse Figueur, the original ''Madame Sans-Gêne'' before Victorien Sardou reused this nickname for Catherine Lefebvre, served from 1792 to 1815 as a cavalry trooper and was wounded and captured a few times.
* [[http://en.wikipedia.org/wiki/Nadezhda_Durova Nadezhda Durova]] (1783-1866), the Cavalry Maiden of UsefulNotes/TheNapoleonicWars, first served in 1806 disguised as "Aleksandr Sokolov". Her distinguished career continued after her true gender was discovered, and as a lieutenant in the Mariupol Hussars became the first Russian female officer. She later wrote memoirs of a quality that impressed [[Creator/AlexanderPushkin Aleksandr Pushkin]].
* [[https://ru.wikipedia.org/wiki/Завалий,_Евдокия_Николаевна Eudokiya Zavaliy]] (1924-2010), the marine corps officer of UsefulNotes/WorldWarII. She joined Red Army as a girl in 1941 after her village was taken by German landing force and worked as a nurse. But later she was commissioned because of injury and put in reserve regiment. Than some officers came to get volunteers to the front-lines they took her for a man (helped by the documents saying "Eudok.", which can be the beginning of both Eudokia ''and'' Eudokim). She decided to play with and soon became a platoon commander. After her real gender was uncovered 8 months later (as usual, in a hospital) she was sent to the officers courses and became the one and only female Marine corps officer in Soviet history. She retired in 1947 in rank of guards colonel. She and her marine platoon was so feared by Nazis that they called her Frau Schwarzer Tod (Miss Black death).
* During the UsefulNotes/FrenchRevolution farmer's daughter [[http://en.wikipedia.org/wiki/Ren%C3%A9e_Bordereau Renée Bordereau]] (1770-1824) lost several relatives to the Terror and and saw [[YouKilledMyFather her father killed before her eyes]]. Dressed as a man (not that hard, apparently, as she was described as very ugly) she fought in the wars in the Vendée on the royalist side under the ''nom-de-guerre'' Langevin (i. e. "the Angevin" or "man from Anjou") and was wounded several times. Since the forces of the Republic and Empire kept looking for a man, she managed to evade capture after the Vendéans' defeat until 1809. At one point she was accused of raping a girl, but was able to prove her innocence by revealing her gender, but not her real name. Imprisoned on the Mont-Saint-Michel, she was liberated after Napoleon's abdication, following which she dictaded her memoirs before taking to the field once more in the war of 1815.
* As per the ''Assassin's Creed IV: Black Flag'' example, [[http://en.wikipedia.org/wiki/Mary_Read Mary Read]] and [[http://en.wikipedia.org/wiki/Anne_Bonny Anne Bonny]], two Sweet Polly Olivers on the same ship, no less! Apparently the practice of women joining pirate crews disguised as men was common enough for Black Bart to specifically forbid it in his formulation of the pirates' code. Ironically, both escaped hanging because they claimed to be pregnant, since it was a pretty standard way of forestalling a death sentence, as there wasn't any immediate method to definitively confirm the allegation. Read later died of a fever while in prison, while Bonny disappeared from the record.
** Not to mention that Bonny was hitting on Read, and ended up being the victim of an UnsettlingGenderReveal, after which she [[TheReveal revealed]] her own disguise to Read.
** Read went on to fight a duel to save another (presumably) male pirate she was interested in. She allegedly won the duel by [[WardrobeMalfunction tearing open her shirt]] and then skewering her opponent [[DistractedByTheSexy while he was distracted]].
* Mollie Bean, who is known only from an 1865 article in the Richmond Newspaper, after she was discovered. She served in the 47th North Carolina Regiment disguised as a boy for over two years. Was included as a character in Creator/HarryTurtledove's ''The Guns of the South.''
* Also [[http://en.wikipedia.org/wiki/Catalina_de_Erauso Catalina de Erauso]], "The Lieutenant Nun".
* Mexican female writer Sor Juana Inés de la Cruz, back in the 17th century, crossdressed in order to sneak into an university back when women were not allowed to receive education. She later decided to become a nun and spare herself from TheReveal.
* The book ''Female Tars: Women Aboard Ship in the Age of Sail'' by Suzanne J. Stark gives several examples of women who joined the British Royal Navy in disguise (as well as exposing a few frauds). Includes a detailed autobiography of Mary Lacy, who served as a seaman and shipwright for twelve years.
* [[http://en.wikipedia.org/wiki/Norah_Vincent Norah Vincent]] posed as a guy for one and a half years, exploring the male-only parts of the society (including a Catholic cloister) out of pure scientific interest. Nobody guessed that "he" was a she the whole time.
* [[http://www.newscientist.com/article/mg19726462.000-histories-the-male-military-surgeon-who-wasnt.html James Barry]], a nineteenth-century British Army surgeon, was born Margaret Ann Bulkley. Bulkley became Barry in order to be accepted into medical school, half a century before women were officially allowed to study medicine in Britain. She maintained that identity throughout a long and distinguished military career, continuing the ruse until her death. Barry served all over the British Empire for fifty years, and worked hard to arrange better sanitation, food, and medical care for soldiers, prisoners, and civilians alike. She also performed one of the first successful Caesarians in history.
* Charlotte "One-Eyed Charley" Parkhurst, a stagecoach driver during the Gold Rush, who wasn't publicly outed until after her death.
* [[https://en.wikipedia.org/wiki/Milunka_Savic Milunka Savic]], a Serbian war heroine from UsefulNotes/WorldWarOne, was a rather awesome subversion of this trope. She joined the Serbian Army during the Second Balkan War in the place of her brother after he was drafted, and served with distinction until she was wounded in combat and her gender was revealed to the attending doctors. Her commanding officer wanted to transfer her to the [[StayInTheKitchen nursing division]], but she responded that she only wanted serve as a combatant. The officer said he'd think it over; one hour he granted her request. Yes, she was such a bonafide badass that the military ''literally couldn't waste her as nurse''. According to some sources, her subsequent career in WWI may have made her the most decorated female combatant ''of all time''.
* It's common in [[http://www.nytimes.com/2010/09/21/world/asia/21gender.html?_r=1&ref=world Afghanistan]] for mothers with no sons to dress young girls as boys to escort women of the family and support the family. Mothers with no sons are often pitied, and having what looks like a boy in public improves their image. Then the "boys" suddenly have to become wives, without knowing ''any'' domestic skills or even how to wear a burqa...
* There have been wild rumors that the [[JidaiGeki Sengoku Period]] warlord UsefulNotes/UesugiKenshin was a woman masquerading as a man. ''VideoGame/SengokuBasara'' and the live action drama ''Fūrin Kazan'' reflect this by depicting Kenshin as apparently male but beautiful and androgynous.
* Let us not forget Hatshepsut, Egypt's female King.
** And Cleopatra, for that matter, who often wore a false beard and dressed in male clothing.
* This used to be common in the Royal Navy. So common that chiefs would regularly shout ShowSomeLeg to make sure a given sailor was male before sending him to work.
* After the [[UsefulNotes/TheNapoleonicWars Battle of Trafalgar]] a naked woman was found floating in the [[WarIsHell wreckage]] by sailors of HMS Pickle. They chivalrously gave her some clothes and listened to her story. She was sailing with her husband in disguise aboard the French ship Achille. When her ship caught on fire she removed her clothes and jumped overboard. She swam toward some shipwrecked clinging to a spar. When they kicked her off she floated in the water until she was picked up by the British.
* [[http://www.nytimes.com/2008/06/23/world/europe/23iht-virgins.4.13927949.html?pagewanted=1 Albanian sworn virgins]] are women who took a vow of virginity and became a man in the eyes of society. There are many reasons for this: no male heir, escape from arranged marriage or poverty, when only men can actually work. Although their oath is usually taken in the front of family or local community, most of the sworn virgins don’t bother to inform newly met people about their true gender. This can lead to some embarrassing situations e.g. during hospitalization.
* Jeanne Baret, the botanical assistant, housekeeper, and possible lover of the French naturalist Philibert Commerçon, accompanied her master when he joined the Bougainville expedition; since women were not allowed to serve on French ships, she traveled in disguise under the name of "Jean Baret". Commerçon pled ignorance when the deception was revealed.
* A British Army doctor in UsefulNotes/WW1 was found after "his" death to be female. Examination of her body revealed that she'd also given birth at some point. Sadly, as she'd obviously enrolled under an assumed name, her real identity was never discovered.
* There was also half-legendary Polish student, Nawojka, who attended Jagellonian University disguised as a boy. She was discovered and removed from the university (though not charged with anything specific), but eventually went to a convent and became a teacher there. Her story was supposed to happen in early 15th century.
* Jazz musician Billy Tipton surprised a lot of people, including immediate family, when it was discovered at his death that he was female, born Dorothy Lucille Tipton, who'd been living as a man for almost half a century, and had even been in intimate relationships with women who were certain their partner was male.
* Some French officers during the Napoleonic Wars, most notably Marshal Masséna, had their mistresses dress as staff officers so that they could accompany them on their campaigns, although the disguises were often rather thin.
* In the earliest days of the Boy Scouts organization, girls who wanted to participate occasionally dressed in their brothers' clothing and came to meetings under male aliases. This largely ended when the Girl Scouts were founded, although some SweetPollyOliver scouts maintained the ruse long enough to finish scoutcraft projects in progress.
* Japanese has a surprisingly simple word for this, ''dansou'' (男装). It's also common for all-female acting troupes to have women who play boys' roles, often ''only'' boys' roles. In these cases, the actress may even appear as a man in public, despite being a woman, because it's "easier" for her fans to see her as a him (even if her gender is an OpenSecret).