A popular sub-genre of GenderBender comedy ([[CerebusSyndrome and increasingly, drama]]).

Our protagonist is a [[DifferentForGirls stranger trapped in a strange land]]. They need to infiltrate the social fabrics for [[MacGuffin one reason or another.]] Often, this reason is survival. Problem is, their true gender, if noticed, wouldn't allow them to blend in. Maybe they would be stuck in a ghetto or cage or breeding farm. Maybe they would be expelled. Maybe they would be killed...

But our protagonist does what he/she has to and becomes a WholesomeCrossdresser who will attempt to integrate himself/herself into the setting. How well, and for how long, is what drives the plot.

As a rule, the establishment is draconian and ironclad in its traditions, and is more often than not [[StrawFeminist militantly hateful]] [[StrawMisogynist towards the gender it excludes.]] Through his/her sensitivity, kindness and unique "outsider" perspective, our hero/heroine will (usually) challenge the preconceived and narrow perceptions of his/her fellow cast members...

...and with a little bit of luck, change the establishment into one of kindness and tolerance by the time his/her true gender is exposed.

Note if you're a Japanese-male character on this adventure, you'll more often than not fall victim to the GenderVocabularySlip, as Japanese is a language with ''very'' gender-specific pronouns for men and women to refer to themselves with.

Compare SweetPollyOliver.
[[AC:{{Anime}} and {{Manga}}]]
* ''OuranHighSchoolHostClub'', in which our heroine Haruhi is talked into joining the club and masquerading as a wholesomely sweet boy to cater to their female clientele. It deviates from the usual formula in that her clubmates, at least, are fully aware of the ruse and it's not really Haruhi (who simply has boyish tastes in clothing and hairstyle, and is entirely indifferent to what sex people think she is) trying to maintain the masquerade, but ''everybody around her''.
* ''IMyMeStrawberryEggs'' started out as this, with the HotBlooded young teacher trying to prove the tyrannical StrawFeminist organisation's disdain of men wrong... only to fail bitterly. [[spoiler: It turns out he's not the only one doing it, though.]]
* ''OtomeWaBokuNiKoishiteru'' is one of the funniest and most heartwarming examples in anime, wherein kind-hearted WholesomeCrossdresser Miyanokouji Mizuho becomes the most beloved "OneeSama" and a pillar of strength of his circle of friends in a Catholic Girl's School.
* In ''MariaHolic'', the crossdresser in question is actually ''not'' the main character. He is also ''apparently'' a cruel person who cares not one whit about other people.
* In the first OVA of ''Anime/ElHazardTheMagnificentWorld'', after finding himself in another dimension, the main character Makoto is forced to crossdress in order to pose as the missing princess Fatora.
* The manga series ''GirlGotGame'' is about a high school girl named Kyo Aizawa who disguises herself as a boy in order to join Seisyu High's famous men's basektball team. However, it was her father's idea; she'd rather go to a normal school as a normal girl.
* The manga series ''Manga/MintNaBokura'' is about a boy whose [[HalfIdenticalTwins twin sister]] transfers to a boarding school to be closer to the boy she has a crush on. He transfers to the same school because he doesn't want to be separated from her, but there's a catch: the boys' dorm is full, so he has to disguise himself as a girl and live in the girls' dorm.
* In ''Manga/HanaKimi'', a Japanese-American girl wanted so much to meet her idol she decided to enroll the same school he attends. The problem is that he attends an all-boys school. He soon found out and started to like her. The plot point is that he doesn't know she likes him and she thinks he still doesn't know she's a girl. [[spoiler:When rumours start to abound of a girl on campus and her facade starts to crack via various Bridget-droppings, she decides to transfer to a public school while the going's still good, though [[BittersweetEnding she and her idol meet up again in college and become an item in the epilogue]].]]
* The manga series ''Manga/AKB49RenaiKinshiJourei'' is about an OrdinaryHighSchoolStudent cross-dressing to join an all-girl [[IdolSinger idol group]] so that he could secretly protect his crush, who is also in the same group.
* In ''MarugotoAnjuGakuen'', our protagonist is pretty much ''forced'' to join an all-girl academy for yokais by his mother.

* ''FanFic/FutariWaPrettyCureDragon'' has a male protagonist who winds up accidentally enrolling in a girls' school because he was trying to hard to pass an entrance exam after failing so many. The other protagonist is a girl through and through, and she finds out in the first episode right before they become the titular magical warriors.

* The truly [[{{Squick}} squick-tacular]] Wayan Brothers film ''WhiteChicks'' has two black male police officers masquerade as [[UncannyValley weirdly plastic-looking]] white valley-girls.
* Amanda Bynes in ''Film/ShesTheMan'' (which is a SettingUpdate of ''Theatre/TwelfthNight'') infiltrates an all boy's soccer team to prove that girls can play soccer just as well.
** And two decades earlier, a girl infiltrates another high school's senior class as a boy to try to prove gender bias in her school's newspaper in ''Film/JustOneOfTheGuys.'' The fact that her name was Terry didn't hurt. The funny part is, she failed miserably -- turns out her writing to start with wasn't very good -- but the Theatre/TwelfthNight plot helped her to improve.
* Disney's ''Disney/{{Mulan}}''. This trope actually gave the family film some unexpected and refreshing [[ParentalBonus parental bonuses]].
** Although one does notice that the character is drawn differently when she pretends to be a man. Look at the movie poster where half of her face is reflected in a sword. Notice her nose and jaw.
** And apparently her eyebrows grew in no time.
** Notice that this is based on an old Chinese poem "Poem of Mulan", making it older than Shakespeare.
* Dustin Hoffman in ''{{Tootsie}}''.
* ''{{Yentl}}'' had this, as it was set during a time when women were not to become educated.

* TamoraPierce's ''Literature/SongOfTheLioness'' series starts as a more dramatic example of this plot with Alanna becoming a SweetPollyOliver so she can become a knight, though her gender gets revealed at roughly the halfway mark.
* The male protagonist of ''Literature/APlanetCalledTreason'' develops breasts due to a genetic disorder and parleys it into the opportunity to infiltrate an all-female society.

* ''Theatre/TwelfthNight'' by Master Creator/WilliamShakespeare, obviously, created this OlderThanSteam genre and [[TropeNamer named this trope.]]