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Disguised in Drag

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"Uh... Olsen, when we said that this story would call for staking out Luthor in 'casual dress'..."
"Sirrah, go you to Barthol'mew my page,
And see him dress'd in all suits like a lady;
That done, conduct him to the drunkard's chamber,
And call him 'madam,' do him obeisance."

Any scenario where a character dresses as a member of the opposite gender for purposes of disguise. In many cases, this results in Incredibly Conspicuous Drag; for example, if the character in question is a man, his square jaw and broad shoulders will make him look like an Amazon at best or a guy in a kitschy Halloween costume at worst... but it's still good enough to fool others most of the time. He may have the right body type and facial structure to look genuinely attractive as a woman, but Attractive Bent-Gender is likely to come into play in either case.

Frequently, but not invariably, Played for Laughs, though this may lead to some Values Dissonance as making fun of gender non-conforming people becomes less acceptable. If the character is a man dressing as a woman, this trope will often result in An Aesop about walking a mile in women's shoes.

Subtrope of Crossdresser. If the character wears opposite-gender disguises more often than seems strictly necessary and/or seems to like it to some degree, then they also qualifies as a Wholesome Crossdresser or Creepy Crossdresser depending on the character.

Not to be confused with Dragged into Drag, though they may overlap if the subject is unwillingly forced into the disguise, whether by others or by circumstance.

Sweet Polly Oliver is the Distaff Counterpart of this trope but is more likely to be Played for Drama.

Harmless Lady Disguise is a subtrope, as is Hiding in a Hijab.


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    Anime & Manga 
  • In Ah! My Goddess, Keiichi has to dress up as a woman at one point to avoid the wrath of an ex-boyfriend of Urd's who likes cursing any men who get close to her. Him having coincidentally gained long hair and breasts from drinking some of Urd's potions not too long ago helps his disguise.
  • In Anohana: The Flower We Saw That Day, Yukiatsu disguises himself as Menma to fool the other Peace Busters and to relieve his own obsession of her.
  • Legoshi of Beastars, to avoid needing to cut his fur short again, crossdresses in order to speak with his friend Louis, who is currently the leader of a criminal organization that wants Legoshi dead.
  • Black Butler:
    • A plot point for episode 4. And one guess who got dragged into the drag. Give up? Ciel.
    • In season two we have Alois briefly disguising himself as a maid.
  • Black Cat:
    • Train has this happen to him in the anime. Also coupled with him turning into a cute little boy (due to being shot with a Lucifer bullet). Due to him shrinking in size, no one else except Eve has clothes his size - so he ends up having to wear her dress temporarily. The saddest part? He looked damn good in it.
    • And Sven, also in the anime. Y'see, they needed bait to lure out a Serial Killer who preferred to target women, and Sven's chivalrous attitude just wouldn't allow him to let Eve do it, so... Averted in the manga, where he did let Eve do it, reluctantly.
  • In Brave10, because he would have been killed if it were found out any of the original Ishikawa Goemon's sons were living, the Ishikawa Goemon seen in this series starts living as a woman to deter rumours.
  • Conan Edogawa from Case Closed and Kaitou Kid from Magic Kaito have both shown no issues with disguising themselves as girls when it helps their current plans.
    • The first case that includes Kaitou is both squicky and funny since Kaitou steals Sonoko's mother Tomiko's very expensive black pearl while perfectly disguised as Ran, which strongly implies that he drugged, stripped her and perfectly studied her... er, features so he could pose as her better. Conan himself goes completely red when confronting and unmasking Kaitou, realising the implications of a nude Ran hidden somewhere... Fortunately, Kaitou is polite enough to not steal her gown, only using a similar dress.
    • Played with much later: Kaitou knocks out and strips Sera to disguise himself as her, leaving her Bound and Gagged in her undies... but Sera is such a Bifauxnen and so flatchested that he doesn't notice it's a girl. (To be fair she is wearing boyish underwear and an undershirt at that moment. Sera was also caught in the men's washroom because the women's washroom was full.) Conan later explains everything, Kaitou is all "WTF?!" when told Sera's a girl... and cue to a very pissed off Sera in her undies drop-kicking him in the head.
    • Conan once switched clothes with Ayumi to find some kidnappers (they wanted her to deliver the ransom).
  • Code Geass had three male characters do this in one of the picture tracks. We had Rivalz and Suzaku, but also Lelouch. In a later one, Lelouch was forced into a bridal dress. This scene was then added into the visual novel game Code Geass: Lost Colors. It was truly hilarious, considering he makes a rather attractive woman. Suzaku does it Lost Colors again as well, though it's not quite as attractive, or convincing.
  • Crossplay Love: Otaku x Punk: Shuumei creates his "Mei" persona to be able to get close and talk to Hana, who he worries wouldn't like his male personality. Little does he know "Hana" is also a Crossdresser.
  • This is the entire shtick of Oka Sakuragaoka from D-Frag!. Since he was dressed like a girl when the main character first sees him, he continues dressing like a girl to maintain the masquerade.
  • In D.N.Angel, Satoshi disguises himself as a woman in order to distract Handsome Lech Dark during a heist. It works — he nearly kisses Satoshi before he realizes who he's talking to, and at that point, Satoshi had already handcuffed him to the wall.
  • In Date A Live Shido has to seal, Miku a spirit who Does Not Like Men and has a controlling voice, and the only way to do that is to make her fall in love with him then kiss her. In order to do this, he disguises himself as Shiori, then tries to do just that. While Miku doesn't see through his disguise until the climax (with an unintentional Crotch-Grab Sex Check), it doesn't work out, and he only convinces her to let her powers be sealed after she sees him rescue Tohka from her inversion.
  • In Demon Slayer: Kimetsu no Yaiba, to spare the field inexperienced Aoi Kanzaki from being forcefully drafted into Tengen’s mission of infiltrating a Red-Light District to rescue his contacts (his 3 wives) and exterminate a demon Tanjiro, Inosuke and Zenitsu all volunteer to take the mission in Aoi's place, but since Tengen really needed female slayers he forces the trio to disguise themselves as girls and apply themselves as courtesans. Zenitsu is the one who stands out the most due to circumstances forcing him to go throughout the entire event dressed like a girl, while everyone else eventually broke off the disguise during the nerve-wracking fight against the demons.
  • All three dragon knights do this in the first volume of Dragon Knights, as they are trying to infiltrate a castle that keeps stealing female sacrifices from a nearby village.
  • In Dr. STONE, the Treasure Island arc sees the heroes finding an island ruled by an Evil Chancellor who possesses the device that petrified humanity and ally themselves with Amaryllis, a young woman who planned on infiltrating the chancellor's "harem selection" so she could it. After deciding to have Kohaku go along, Amaryllis points out that having more "girls" would increase their chances, so they try disguising the men present; Senku's voice is too deep, Gen can affect a decent feminine voice but is too tall, and Soyuz is right out because he's too tall, muscular, and bald. The only guy who can pull it off is Ginro, who effectively has to be dragged kicking and screaming the whole way.
  • In Dual! Parallel Trouble Adventure, the local Humongous Mecha can only be piloted by females. So when the male protagonist shows he's compatible, the Mad Scientist in charge of the robots makes up a female-looking pilot suit with voice changer and "shock absorbers". It doesn't last very long.
  • In El-Hazard: The Magnificent World, Makoto, the male hero, happens to look just like the missing princess of the magical land the characters visit. The royal family forces him to impersonate her. That created a very uncomfortable moment with the princess' lesbian consort.
  • In Fist of the North Star, Rei, one of the characters in the series, does this to lure his pursuers into a trap by using his pink cloak and hide his face, but mainly for survival. Then makes his epic reveal when his real gender is shown. It works because of his Bishōnen looks, and he's been trying to find a man with seven scars on his chest (who was revealed to be Jagi, Kenshiro's evil brother who was framing and impersonating him).
  • Honoo no Alpen Rose:
    • In the manga, Jeudi has to crossdress so that people don't recognize she's wanted by the Count.]]
    • Also in the manga, Leon would take advantage of his Pretty Boy appearance and disguise himself as a woman in public so that he wouldn't be recognized as a celebrity.
  • There's one scene in episode 7 of Fractale where Clain Necran does this while roaming a city populated by Doppels.
  • Fullmetal Alchemist: Lt. General Grumman disguises himself as an old woman at one point to meet with Mustang.
  • Fullmetal Alchemist (2003): ** Edward Elric has disguised himself as a girl only once. Whether or not that was successful would be difficult to say.
  • In a manga-only part of Fushigi Yuugi (and a series of short segments after some of the anime OAVs), the Suzaku warriors wash up on the shores of a matriarchal society after shipwrecking, and are forced to pass as women. Played for high hilarity when Gentle Giant Mitsukake reveals himself as a woman, only for it to be digitally pixelated out because it's too horrible to look at. More hilarity is mined when Chichiri turns himself into an adorably gorgeous young woman, prompting a jealous reaction from Nuriko, who's been crossdressing since the beginning of the series and is horrified that someone might make a prettier woman than him.
  • In Arina Tanemura's manga (examples include The Gentlemen's Alliance and Sakura Hime: The Legend of Princess Sakura), disguise can actually change a boy's physique: he really looks like a girl.
  • In the Get Backers manga, this is one of Ban's *ahem* genius plans to try to get them into a prison. He has both him and Ginji dress in schoolgirl uniforms and try to pretend that they're on a field trip and want to visit the prison. It doesn't work. Though they actually do look quite cute in it...
  • Great Teacher Onizuka:
    • Onizuka dresses as a Joshikousei to infiltrate Anko and her friends' karaoke party. They see through it pretty quickly, but not in time to escape their punishment for bullying Noboru.
    • When Teshigawara kidnaps Fuyutsuki, Onizuka puts on a wig and the wedding dress that he'd put on her, and lies in wait, sitting on the bed facing away from him. Teshigawara doesn't realize who it is until he gets close enough for Onizuka to clobber him.
    • Onizuka does this again in Shonan 14 Days, when he even more unbelievably impersonates a teenage girl (Sakurako) to beat up her father when he tries to molest her. The father does notice Onizuka's shoulders are unusually broad for a girl, but not in time to avoid an ass-kicking.
  • Gundam:
    • Mobile Suit Gundam ZZ had Judau and Iino crossdressing in order to infiltrate the base of a gang leader who's trying to form his own harem. Humorously, while Iino gets in easily, Judau gets turned away because he looks downright weird in a dress.
    • A major plot element in the first half of ∀ Gundam is that the androgynous male protagonist Loran is known to the public as a girl named "Laura Rolla". Loran dresses the same most of the time, though he may need to switch to a feminine voice and speech, but twice had to get all dolled up for a gala (very convincingly). The idea was concocted by Guin Sard Lineford, who for vague reasons claims it's diplomatically better if the Moonrace believe the White Doll was piloted by a woman. Given Guin was heavily implied to be in love with Loran, and had been calling him "Laura" since they first met, he probably just wanted to see Loran in a dress. Loran goes along because he wants to keep in contact with the Moonrace, which will be impossible if they know he's an enemy pilot.
    • Happens to Tieria in Mobile Suit Gundam 00, when he must infiltrate a high-class party. The thing is, he's androgynous enough to pull it off; anyone who didn't know his true sex would be utterly fooled. He rationalizes it as a good disguise because all Gundam Meisters are known to be male, but Wang Liu Mei (and the viewers) guesses that Sumeragi was having a bit of fun at his expense.
  • Hare from Haré+Guu was disguised as a girl once.
  • Harukanaru Toki no Naka de - Hachiyou Shou has an episode where the main group is trying to help a young couple and comes up with a plan that involves impersonating them. When the option of Akane playing the role of the girl gets rejected for being dangerous, Eisen suggests that one of the Hachiyou could dress as a woman... and everyone immediately agrees that he is perfect for this task. (Eisen should have accounted for the fact that he is pretty enough to pass as a girl without much effort; the man they were trying to fool even offers "her" to become his wife upon discovering that "she" is not the princess he was searching for, but a different girl...)
  • Although not normally used as a disguise, Hermione Ayasaki is once used as such in an alternate story of Hayate the Combat Butler, to keep Hayate from being killed and Izumi from getting in trouble for having a boy in her room from her father. 'She' is hired as a maid by said father, though the other characters see through the disguise easily, as is normal for Paper Thin Disguises within the series.
  • Hetalia: Axis Powers:
    • France once dressed up as a girl to capture Italy. The plan is pulled off without a hitch.
      Italy: Germany, Germany! I was hitting on someone because I thought it was a cute girl, but it was actually France in disguise!
    • Italy himself once dressed up like a woman on April Fools Day in order to trick Japan.
  • In the manga version of Honoo no Alpen Rose, Jeudi crossdresses and cuts her hair to escape from the Count, and a local girl named Liesl hits on "him" (and may be a bit enamoured with "her" even after finding out, and at some point in the manga, Leonhart does this as well.
  • This is the premise of I My Me! Strawberry Eggs, wherein the protagonist dresses as a woman to teach at a school run by a misandric headmistress. At the end of the series, very subtle hints are dropped that his landlady is actually a man in drag, who does so in order to be close to the headmistress.
  • JoJo's Bizarre Adventure:
    • In Part 2, Joseph Joestar decides that the best way to infiltrate a secret Nazi base in Mexico is to don a Harmless Lady Disguise. Since Joseph is a 6'4" colossus with a Heroic Build you could grate stale parmesan on, you can imagine how well it worked out.
      Joseph: Damn, those Nazis are impressive. How could they see through my female disguise?
    • Tsurugi Higashikata from Part 8, since he has to be disguised as a girl until he's 12 in order to ward off a "curse".
  • Kaguya-sama: Love Is War: Since she's supposed to keep her identity as Kaguya's valet a secret from their classmates, Hayasaka has adopted multiple personas including the butler Haysaca-kun for when Fujiwara comes over. She's even given him a complex backstory as an orphaned, gay, crybaby, teen-genius who's graduated from Harvard.
  • The Kaname series of doujins plays this for drama; the titular character Kaname only dresses up as a girl because he feels more comfortable indulging in his gay sexual desires dressed up, otherwise keeping it separate from his "normal" everyday persona as a boy.
  • One-shot Kanojo Ni Naritai!? is about a high school boy who pretends to be a girl to date a classmate who he thinks is a Butch Lesbian. It turns out she is not attracted to girls though.
  • In the manga adaptation for Kingdom Hearts: 358/2 Days, Roxas was forced to wear a French Maid Outfit and pretend to be the White Rabbit's servant, Mary Ann, while trespassing his home to find a way to restore Luxord to his normal size. Unfortunately, it didn't work.
  • Kyo Kara Maoh!:
    • This is how Yuuri first meets Jozak, whose disguise would have been more convincing if Jozak didn't a) have noticeably larger biceps than most women and b) seem to believe that Sleeves Are for Wimps.
    • Jozak is the only one that does it regularly, but if the characters in general need to go somewhere in disguise, there's about a fifty-fifty chance that at least some of them will be going there in women's clothes. It's that kind of a series.
  • In The Love and Creed of Sae Maki, Kokai is a Master of Disguise who cautiously contacts Misao with We Do Not Know Each Other tactics to stay under Sae's radar. Once Misao is walking down the street when a middle-aged housewife in an apron gives her instructions on where to meet—Kokai in drag.
  • Lupin III:
    • Lupin is a Master of Disguise and does this often. Either disguising himself as a female ally (such as Femme Fatale Fujiko), someone the target knows to get close to the loot or to fool security at a venue he's about to hit. It has backfired on him on at least one occasion when the man he was planning on robbing fell in love and proposed. The reveal did not dissuade him.
    • He also wore a Spy Catsuit resembling that of the resident "beta girl" of Lupin III: Island of Assassins in one scene.
    • Goemon, Jigen, and Fujiko (the latter as Lupin himself in at least one case) have also been in cross-gender disguises for jobs, usually most unwillingly. And one volume of the Lupin III Y manga had them all in drag to fool both Zenigata and their target.
    • Zenigata himself has also gotten into the action, in one episode disguising himself as Fujiko, and in Farewell to Nostradamus as a Brazilian carnival girl.
    • In Lupin III: The Woman Called Fujiko Mine episode 6: Oscar disguises himself as the targeted schoolgirl to trick Fujiko and Lupin.
  • Unsurprisingly pulled off by Alto Saotome in Macross Frontier Sayonara no Tsubasa where he dresses up as a maid in an attempt to rescue Sheryl.
  • Mazinger Z: Done by — of all people! — Baron Ashura at least twice (in episodes 7 and 36). He/she disguised like a woman to manipulate a mob or frighten nosy people away one of his/her operations. Fortunately he/she was a shape-shifter, so it was not so hard looking like a woman how it would be to him/her (on the grounds of Ashura being half-male, half-female). It overlapped with Creepy Crossdresser since it was pretty squicky -and eerie-.
  • Mint na Bokura is about a boy who disguises himself as a girl so that he can attend the same boarding school as his sister.
  • Mob Psycho 100: In one chapter, Mob and Reigen have to sneak into an all-girls school disguised as students to meet with some clients. Mob is rather embarrassed about the whole thing, especially when the security guards see right through Reigen's disguise but not his.
  • In Monster Rancher, Hare devises a plan to sneak Holly and the Stone safely away from their enemies, by having Genki and Holly swap outfits and then have Genki run interference while Holly slips quietly away with Tiger. Unfortunately, Lillim saw through it.
  • Moriarty the Patriot: In the first chapter of The Remains, William is dressed as a woman to play his brother's fiancee on a trip to Durham so he's not recognized in his old home and won't bring trouble there.
  • My Daemon: In the episode "Impurity of Peace", Kaede and Ichinose sneak Kento into the Peace Organization building by having him pass as a student in the school group having a field trip there that day, further disguising him by having him wear a girl's uniform and hair clip. He has an androgynous enough appearance that it works to get him in, but one of the students notices his discomfort and gets suspicious upon not recognizing "her" from any of their classes, and Kento has to take advantage of a convenient distraction to sneak away and meet up with Kaede, whereupon he changes back to his regular outfit.
  • My Monster Secret:
    • Ryou Aizawa is a six-inch-tall male alien who pilots a female Mobile-Suit Human, primarily for the purpose of extorting money from the resident Casanova Wannabe. This results in no end of Squick for the characters who are aware of his actual identity.
    • A rare unintentional example occurs in the case of Genjirou Shirigami when he comes to Youko's school to find out if her secret (she's a vampire) has been exposed. Unfortunately, he requested that Akane magically disguise him, and Akane being Akane, she obliged by making the disguise female.
  • In Otoboku - Maidens Are Falling For Me, the main character spends most of the series in this kind of disguise—that is, he passes for several months at an all-girls school, despite being found out more than once.
  • PandoraHearts:
  • Pokémon: The Series:
    • In Pokémon: The Original Series, Ash had to disguise himself as a girl to gain access into the Celedon City Gym, as he had offended Erika, the Gym Leader, earlier in the episode. It went on to become a Running Gag Once a Season, though usually it's not a disguise.
    • In Pokémon the Series: Black & White, Ash, Pikachu, and Cilan had to crossdress in order to get into an all-girls club. Iris (the only actual girl of the group at this point in time) instigated it.
    • The aforementioned Running Gag reversed itself in one episode of Pokémon the Series: XY when it's Serena who has to masquerade as Ash while he's incapacitated.
    • If Team Rocket uses a disguise that involves a female and a male role, James will almost always dress as the female. (And very lovely he looks too.) Logically, then, this also applies to Jessie, who has dressed as a man on several occasions (though she doesn't seem to crossdress as much as James does.) They've mostly stopped crossdressing since Johto, but it will sometimes pop up (such as one case in Sinnoh where James had to use Jessie's contest disguise for a similar reason as to Serena's case listed above).
    • In Pokémon the Series: Ruby and Sapphire, minor recurring villain Brodie is a Master of Disguise, and he's able to pretend to be people of either gender with ease. Notably, in his first appearance, he spent most of his time disguised as a female scientist; the only time his cover came close to being blown before he revealed himself was when Brock actively stopped himself from flirting with "her", much to everyone's confusion.
  • Ranma ½:
    • Ukyō is a cross-dresser herself, and that's probably the reason why she attracts cross-dressers. Both of her love interests (other than Ranma), Tsubasa and Konatsu, look very convincing as girls because they've already got feminine features. Thanks to his parents, Konatsu the "Cindrella boy" is actually more beautiful than his step-mother and step-sisters could ever be (and what was his late father thinking?).
    • In order to distract the Orochi, a giant pervert who loves girls (to look at as much as to eat), Ranma, Ryōga, Shinnosuke, and Shinnosuke's Grandpa crossdress (namely, a schoolgirl, a nurse, a policewoman, and a bride). The funniest part is that Ranma does this as a man (had he done it as a woman, the Orochi would've made a beeline for her).
  • In RIN-NE, Rinne decides to dress in a maid uniform to try and capture a damashigami who is kidnapping school girls. It works. He actually has to unmask himself as male to his opponent when he defeats him. He then takes advantage of his situation to win the school's Mr. Lady competition. While Sakura and her female friends agree he looks cute, Tsubasa is at a loss for words.
    Rinne: How do I look?
    Tsubasa: How am I supposed to answer that?
  • During the yuki-onna arc of Rosario + Vampire, Tsukune has to disguise himself as a girl to get into the coming of age ceremony, where men aren't allowed.
  • Samurai Champloo: Jin does this to get into a brothel. However, despite his Bishōnen looks, the thugs guarding the brothel are suspicious and insist he play the instrument he's carrying. Jin fails dismally and so whips off his disguise.
    Thug: Crossdressers! I mean... double-crossers!
  • In Shounen Oujo (literally Boy Princess), Albert is a peasant child in a matriarchal society who is bought by the princess Alexia (whom he greatly resembles), in order to serve as her decoy while she sneaks out to see the queendom she will one day rule. The twelve-year-old Alexia is assassinated at her coming-of-age ceremony and Albert steps in to take her place on the spur of the moment, leading to him spending the next two years posing as a girl in every aspect of his lifestyle, going so far as to use herbal and beauty treatments to stave off puberty.
  • Slayers:
    • The heroes have to go to a Holy City where priestesses are trained and all permanent residents are female. They get involved with the ruler's child who does not want to be a priestess and is in fact male and forced to crossdress by his overbearing mother. At the end, it is revealed that the "all-female community" is in fact fifty percent male.
    • Gourry also has to disguise himself as a woman in a couple other episodes (always episode 17 of the season). Only Evolution-R averts this tradition, being a Bizarro Episode instead.
  • SpillItCocktailKnights: Sora spends her life as a boy to hide her secret identity as a Magical Girl. Her best friend, who has a Celebrity Crush on her, has figured out her secrets, but hasn't told anyone, including her.
  • Spy X Family:
    • Loid attempts to disguise Frankie as a woman so he can play the role of his wife and Anya's mother for Eden academy's family interview. It doesn't turn out well.
      Anya: I don't want this mama.
    • In "Short mission 2", Loid disguises himself as a woman to help Frankie practice going on a date with a woman he likes.
  • In Tokyo Ghoul:re, Haise Sasaki goes undercover on a mission to learn about the ghoul auction with his group of investigators (the Qs), and everybody except for Saiko (already female) dress up as women because the ghoul they were investigating, Nutcracker, was recently targeting young women to lure them into the auction.
  • In the second season of Vandread, it turns out that BC was a guy the whole time, serving as a spy for Tarak.
  • In Wild Rock, because Yuuen is an incompetent huntsman and a bit of a runt his father gets him to dress up as a woman for a Honey Trap ploy to get more food.
  • Aoi from You're Under Arrest! had to dress as a woman in order to catch chikan. Eventually she began living full-time.
  • In one episode of Yu-Gi-Oh! 5D's, Lua disguises himself as his twin sister Luca to enter a tournament because she doesn't want to enter and he wasn't invited. Once he actually gets onto the field he doesn't even bother acting like a girl, except to pretend very badly when his opponent points out that he's a boy.
  • In the YuYu Hakusho manga, Yusuke pulled this off pretty well and looks like quite a convincing girl believe it or not.

    Asian Animation 
  • In Happy Heroes, antagonist Big M. has a tendency to dress up in feminine disguises as part of his many, many villainous schemes. Considering he's a gonk whose face makes people vomit on sight, he doesn't make a very attractive woman, which is Played for Laughs.
  • Motu Patlu:
    • In "Angry Clouds", Patlu dresses Motu up as a woman in an attempt to keep the Rain God from recognizing him.
    • In "The Revenge of Crows", Ghasitaram suggests that Motu and Patlu disguise themselves as women to keep the crows from recognizing and bothering them. The crows still recognize them through the disguises and proceed to keep pecking at their heads.
  • Wolffy from Pleasant Goat and Big Big Wolf might occasionally dress up as a female to aid in his plots to catch the goats. Dressing up as a female goat is actually the first scheme he ever comes up with in the series.

    Comic Books 
  • In the Asterix comic Asterix and Son, prefect Crismus Cactus is forced by Brutus to dress up as a nursemaid in an attempt to get the baby from Asterix.
  • Barracuda: When the Blackdog's pirates capture the Spanish ship, Dona Emilia dresses the servant boy Emilio in her daughter's clothes to save him from the pirates, who are killing all the men. Emilio makes a very convincing girl and is sold as a female slave. He also discovers that he likes dressing as a woman and becomes a Wholesome Crossdresser and one of the most heroic characters in the story.
  • Captain America and Paladin engage in one of the least convincing examples ever recorded in Captain America #387-392 (1991) when they have to pass unnoticed through Superia's base filled with female supervillains in order to save Diamondback (who, at the time, was Cap's on-again-off-again girlfriend). They simply borrow Black Mamba and Asp's costumes (which, incidentally, are skintight) and put them on, with no further attempt at disguise (they don't even wear wigs!), trusting that the presence of a number of Brawn Hilda types among Superia's followers will be enough to deflect suspicion. It works!
  • The Dead Boy Detectives 2005 graphic novel: Charles and Edwin are shoved into womens' clothing and makeup so they can blend in at the girls' school.
  • In the Disney Mouse and Duck Comics Donald Duck has surprised a lot of people, including Mickey and Daisy (his girlfriend) with his willingness to put on such disguises whenever necessary to help someone.
  • Fanhunter: The Liquidator, a parody of Terminator, is a muscled male robot coming from the future. Naked, he looks for the clothes of a nearby person. He uses the clothes of a female Flamenco dancer, believing it is some kind of urban camouflage gear. It's a comedy after all.
  • Madam Fatal: Back in the '40s, retired actor Richard Stanton fought crime under the alias "Madam Fatal".
  • The Mighty Thor has a story that adapts the Thrymskvitha poem. This means that, yes, Thor has to dress in a pink wedding gown and pose as Thyrm's bride-to-be while Loki bends over backward explaining why "Freyja" is 7 feet tall and just as broad across the shoulders. At least he didn't have to explain away a beard in this version.
  • In the Nancy Drew graphic novel The Fake Heir, the villain is a man impersonating his dead wife in order to continue collecting her disability payments.
  • German detective Nick Knatterton did this more than once.
  • At least two versions of Robin have done this:
    • In Batman #626 (2004), Tim Drake has to disguise himself as female medical student Caroline Hill to obtain samples from a hospital. Alfred explains that Tim is too young to pull off a male med student. Tim is not happy about it:
      Tim: I could have been a genius, a Doogie Howser prodigy!
      Alfred: That would attract too much attention.
      Tim: These boobs attract too much attention! Did you have to make them so big?
      Alfred: They're big enough to give you positive attention, but not enough to be remembered.
      Tim: Okay, you put waaaay too much thought into this...
    • Tim's not the only Robin to be in drag. Dick Grayson has been disguised as Marie Antoinette, Lulu Belle and Batgirl.
    • Hell, Batman himself got into the act in Batman #266 (1975). Behold: Bertha Carrington-Bridgewater, in all her splendour.
  • Superman:
    • Jimmy Olsen does this so often he keeps an extensive wardrobe of women's clothing and accessories in his "disguise trunk." Strictly because it's necessary for his job as an investigative reporter. Or at least that's what he says. Crazy-Prepared reporter or Wholesome Crossdresser who found a way to write off his female wardrobe as a business expense? You make the call!
    • A Mind-Switch in Time has a pickpocket caught by Superman who used to disguise himself as a bag-wearing old lady.
    • The Death of Lightning Lad: Ayla Ranzz wears her twin brother's uniform to impersonate him. Unfortunately, she forgot cover her Adam's apple-less throat, and her ruse is exposed.
    • In The Death of Luthor: One of Luthor's henchmen disguises himself as a woman to lure an unwary Supergirl into a trap.
  • At one point in Super Mario Adventures, Luigi disguises himself as Princess Peach in order to distract the Koopalings, leaving Peach dressed in Luigi's clothes. He uses a surgical mask to hide his mustache, which is convenient as he explains he has a cold (which also explains why "her" voice sounds broken).
  • "Cuckoo in the Nest" from Tammy. It was a unique entry in girl's comics, as the main character was a boy who had to pose as a girl (his name was Leslie, but his aunt thought he was a girl named "Lesley", and the money his uncle used to spoil him was to be used pay on school fees at a girl's school, so when the uncle learned that the aunt was going to visit Leslie at the end of term, he had to enroll Leslie at the school and make him pose as a girl for the entire school year or go to prison).
  • In Varmints, one outlaw, Derrick Stafford, is seen in a woman's dress and apron, complete with a wig and bonnet. He ends up catching the eye of a Pinkerton Agent.
  • Wonder Woman (1942): Agent X seems to be a female axis spy with multiple disguises she can slip into to hide, but turns out to actually be a male spy with multiple female disguises.

    Comic Strips 
  • A FoxTrot Sunday strip shows a Lipstick-and-Load Montage of Paige putting on her make-up getting ready to go out. The last panel reveals it to actually be a grounded Peter trying to sneak out of the house disguised as Paige.
  • Rudi: Rudi and his buddy Freddy do this to visit a New Year's Eve party organized by a group of Straw Feminists. It doesn't end well.
  • In Terry and the Pirates, Creepy Crossdresser Sanjak works for the Axis and impersonates a male pilot to infiltrate Terry's Air Force base.

    Fan Works 
  • The "High-heeled Boot" and "Ballroom" segments of the Sherlock Holmes fic 221B concerns Holmes and Watson on a case which somehow requires them to pose as husband and wife. To Watson's chagrin, he ends up forced into the female role. He irritably puts up with the disguise, including a purse, but draws the line at having to dance with Holmes.
  • In Against My Nature Harry disguises himself and Newt as women to get past some Chinese Aurors.
  • Done twice in Calvin and Hobbes III: Double Trouble — Calvin is forced to do this by Chill early on, and later Retro dresses as an old lady in order to hitch a ride.
  • In Cinders and Ashes: the Chronicles of Kamen Rider Dante, Rui was assigned to protect an idol duo from a Kaizo-Majin. He gets the idea to pose as one of them while they run off. He managed to succeed and fight the Kaizo-Majin off for a bit.
  • In The Depths of Darkness a member of Harry's ruling council has him dressed as the Lady of the Southern Lands during the journey to Harry's manor, to deceive rebel factions. The fact that he's surprisingly convincing in this get-up doesn't make it any less uncomfortable for him.
  • In Grave Mentor, Seira disguises Michel this way, and tells him he looks feminine enough that it would raise questions if he tried to pass as a man.
  • In Gravity Falls: Deep Woods' first part, Quest for the Northwest, Dipper has to, at some point, disguise himself as Pacifica (complete with a wig) in order to distract the butlers who are looking for her.
    Dipper: This might be the most embarrassing moment of my life.
  • Rachel The Vampire Slayer: Rachel, Cassie, and Marco try to sneak into a 21+ club disguised as 19-year-old girls and bribing the bouncer.
  • Played with in the Hivefled prequel Reprise: Gamzee escapes from the Grand Highblood's torture chamber and manages to pass unnoticed through the ship while wearing clothes he stole from a female recruit. The male and female subjugglator uniforms don't look different enough for this to really be an example externally, but since a small but painful part of the mental torture inflicted on him involved mockery of his effeminate qualities, it's really not helping his trauma.
  • The AU Fullmetal Alchemist Edvy fanfiction The Seven Names of Envy Angevin involves this as a fairly significant part of the plot, having Envy disguise himself as 'Julia Vasquez', a flirty, sexy Hispanic girl immigrating from the States. It's also how he figures out he likes guys.
  • While Peter is a woman in Peta Parker, she is still known as "Spider-Man", using a voice-modulator to make her sound male.
  • After hearing about how Rapunzel got locked in her room by her father in Safe Harbor, Varian hatches a plan to get her out. When he learns that only the maids could have access to her room, he disguises himself as a girl to infiltrate the castle. Everyone is surprised how well he can pull off the look.
  • In the backstory for SpeakingThroughWrittenWords's Hearth universe, Vash saved himself and his younger sister from an arranged marriage by disguising himself as a woman and wiggling out of it, and disguising his sister as a boy so she wouldn't be seen as an option. As of ''All's Fine That Ends Okay'', only Roderich Edelstein, who Vash was supposed to marry, has caught on to the truth. He takes on the disguise one last time to get Mrs. Edelstein to leave Roderich alone and Hilarity Ensues.
  • In Those That Carry On, Duo Maxwell crosses the Atlantic disguised as a female Federation officer.
  • In Total Lady Drama Island, an alternate universe where all the contestants were meant to be girls, Cody gets accepted by mistake thanks to a computer virus. Rather than correct the mistake, Chris decides to use the opportunity and make him an offer. If he manages to win the show while disguised as a girl without being outed by the other contestants, then he will win four million dollars instead of just one.
  • This artwork depicts Noriaki Kakyoin disguises as a woman in homage to Tequila Joseph disguise and knocks the guards off.

    Films — Animation 
  • Coco: Héctor disguises himself as Frida Kahlo several times throughout the movie. Given his familiarity with Kahlo's seamstress and the fact that he slips the costume off easily while his family members, even the women, all struggle to remove their disguises, we can infer that he's done this a lot.
  • Detective Conan Movie 26: Black Iron Submarine reveals that Grace isn't a Frenchwoman working for the government. "She" is actually Pinga, the most dangerous member of the Black Organization.
  • Kronk's New Groove: Several male characters do this to pass as Kronk's wife, including Pacha, Rudy, two kids, and Kuzco.
    • A variant in the original The Emperor's New Groove, as he's not a human man at this point, but a llama; Kuzco wears a "dress" (actually Pacha's outer poncho) and pretends to be Pacha's wife to get into a diner with a No Llamas sign over the door.
  • The Jungle Book (1967): Baloo disguises himself as a female ape to distract and dance with King Louie in order for Bagheera to save Mowgli.
  • Kung Fu Panda 2: Po while trying to sneak past the wolf guards. Doubles as Paper-Thin Disguise, since it consists of only a kite, two watermelons, and a fan. When a leering wolf moves in for a closer inspection, Po headbutts him in the face.
  • The Lion King (1994): Timon disguises himself as a hula dancer with Pumbaa as a 'dish' to distract the hyenas so Simba can stand up to Scar.
  • Mavka: The Forest Song: When Lukash is prisoner of Kylina (the Big Bad), Kylina's assistant Frol is disguised as Mavka in order to make Lukash reveal where the Fountain of Youth is, with a bag on his head that's lifted once Lukash has talked.
  • At the end of Mulan, Yao, Ling, and Chien-Po (and Mulan herself, in a bit of Recursive Crossdressing) do this to sneak past the Huns. Made even funnier by the reprise of "I'll Make a Man Out of You" playing in the background.
  • Rango: Rango puts on Beans' dress to disguise himself as the female leader of a theatrical troupe when he and his posse sneak into the moles' camp.
  • At the beginning of Disney's Robin Hood (1973), Robin and Little John disguise themselves as female fortune tellers in order to rob Prince John. Robin pulls it off quite convincingly; his buddy would have been revealed if he spoke to anyone up close.

    Films — Live-Action 
  • Ace Ventura: Pet Detective raises this up to borderline Disguised as Transgender, as Lt. Einhorn is actually disgraced NFL player Ray Finkle, who took on the identity of a missing hiker to exact his revenge plot.
  • In Anything For Love (a.k.a. Just One Of The Girls) Chris constantly is pushed around by bully Kurt and his gang. When he has to change to the same school as them, he decides to disguise himself in women's clothes on his way to school to avoid his tormentors. However, the very first morning he runs into two teachers when still dressed up as female... So he's bound to the role. He learns of the advantages soon, when he manages to become best (girl-)friend to cheerleader Marie.
  • In Are You Being Served?, Mr. Humphries disguises himself as Mrs. Slocombe when Cesar catches him in her tent. After he gets out safely, he then disguises himself as a nun.
  • In Armed and Dangerous (1986), John Candy's character and his best friend disguise themselves- John Candy's character dresses like Divine and his best friend (played by Eugene Levy) dresses like the cop from the Village People.
  • Austin Powers: International Man of Mystery has Austin spotting a club employee as one of Dr. Evil's mooks in drag.
  • Big Momma's House stars Martin Lawrence as an FBI agent who is tasked with tracking down an escaped convict and their loot, by going undercover as the estranged grandmother of their former girlfriend
  • In Bill, a comedy send-up of the life of William Shakespeare, one of King Philip's minions keeps finding excuses to dress in drag to further their plots against Queen Elizabeth. If anything, he's more interested in the drag than the actual plot, and ends up making a Heel–Face Turn to act in Shakespeare's theater.
  • In The Birdcage, this trope is used two different times by several characters. The first instance happens when Nathan Lane's character dressed up as the housewife of his gay lover, played by Robin Williams, in order to impress their future daughter-in-law's ultraconservative parents. In the ending, Everyone except Robin Williams's character and son (and the senator's wife and daughter, who engage in Recursive Crossdressing) dress up in drag in order to escape from the paparazzi.
    • The Birdcage is an Americanized remake of the French theatrical (and later film) comedy La Cage aux folles, which features the same trope.
  • The Bold Caballero: When Zorro, Isabella, and her duenna are being held in the dungeons, Zorro and the duenna swap clothes, so that when Zorro is dragged out to be executed, it is only when they have 'him' on the scaffold do they discover that 'he' is actually an old woman, and Zorro, dressed as an old woman is on the roof firing flaming arrows at them.
  • In The Boondock Saints, the character played by (not exactly feminine in any sense of the word) Willem Dafoe sneaks into a mobster household by putting on a wig and a dress. Despite the disguise being horribly unconvincing, the first man he meets nearly jumps on him. Subverted in that he appears too prepared for the role, too eager to engage in it, and too good at slipping into the character. He's never explicitly stated to be a Crossdresser, but he's certainly not the wholesome type, as evidenced by a discretionary cut when the flirtation with the mooks seem to be going to another level.
  • In Brain Donors, handyman Jacques dresses up as a ballerina during the big premiere.
  • In The Cannonball Run, Bradford Compton and Shakey Finch disguise themselves as a pair of honeymooners on a motorbike. Shakey is posing as the bride and is forced to spend most of the race in a blonde wig.
  • Cannonball Run II has Victor (Dom De Luise) J.J. (Burt Reynolds) and Morris (Sammy Davis Jr..) dressed up as exotic dancers to get in to the ranch the race's kidnapped sponsor has been taken to. note 
  • Lots of Carry On films. Usually with cleavage so low and chest hair so thick it verges on terrifying.
  • In Cherry Falls, the Serial Killer is a Creepy Crossdresser who dresses as a woman while committing the murders.
  • In Cruella, Horace sneaks into the Baroness's charity gala dressed as one of the female guests: all of whom are dressed as Cruella. He doesn't even bother to shave first.
  • In Dad's Army (1971), Mr. Mainwaring claims that German spies disguise themselves as nuns once they parachute into England.
  • In Delusions of Grandeur, Salluste dresses as a Spanish Grand Dame to approach his ex-valet Blaze. He really needs the disguise, because he's one of the most hated people in Spain — the mob is burning his effigy right next to a public place.
  • The opening strip club raid in District 13: Ultimatum sees Cowboy Cop Damian investigating some gangsters while disguised as one of the dancers. He then interrupts the deal by removing his blonde wig, and an ass-kicking ensues.
  • Doctor... Series:
    • In Doctor in the House (1954), Grimsdyke tries to pass himself off as a nurse to avoid being arrested after the riot.
    • In Doctor in Trouble, Ophelia disguises Dr. Burke as "Miss Lavinia Edna Paxenbury" to help him hide from the Master-at-Arms.
  • In Don Juan DeMarco, the title character is enslaved and purchased by a Sultana, to serve as her, *ahem*, personal attendant. To conceal him from the Sultan, he's disguised as a harem girl; a masquerade he pulls off quite convincingly (being played by Johnny Depp can only help.)
  • Dr. Wai in "The Scripture with No Words" has an infiltration scene where the titular hero (played by Jet Li) and his sidekick, Shing (Takeshi Kaneshiro) infiltrates a banquet while disguised in wigs, jewelry and fake boobs. Not a first for Jet.
  • In the martial arts film The Emperor and His Brother, one of the Red Lotus Clan's infiltration attempt in the Manchurian palace had their Fat Idiot manservant, Fan, disguised as a concubine, despite the character in question having a moustache. Disney's Mulan probably got their idea from that old movie.
  • One of the segments in Woody Allen's Everything You Always Wanted to Know About Sex* (*But Were Afraid to Ask) involves a secret transvestite who, through a series of complications, gets caught outside while dressed in a woman's clothes and attempts to pass himself off as female (while covering his large mustache with his hand) while a large crowd gathers.
  • In Experiment In Terror a bank teller under surveillance by the FBI goes to the ladies' room and thinks she's safe even when a hunched over older woman enters. Then she hears the wheezing breath of the man who has been tormenting her.
  • In Free Ride, Stockman's spy takes the simple task given him, to follow Gary and his friends everywhere, a little bit ''too' seriously when he follows them to a mixer at the nearby finishing school for girls. Inexplicably, he spends the rest of the movie in his disguise.
  • Le Gendarme et les extra-terrestres: Cruchot disguises himself as a nun to avoid being caught by Gerber (the whole brigade believes him to be crazy and wants to keep him locked).
  • Le Gendarme et les Gendarmettes: Cruchot disguises as a gendarmette as bait for the bad guys, rather than letting his wife take the role.
  • Girl Happy: Yes, folks, Elvis in drag.
  • In Good Burger, Ed and Dexter disguise themselves as women to sneak into Mondo Burger. They are unmasked and stripped. Ed is also wearing lingerie.
  • The 1975 Soviet film Hello Im Your Aunt (loosely based on Brandon Thomas's play Charley's Aunt) has a homeless man being blackmailed by two young gentlemen named Charlie and Jackie into pretending to be Charlie's aunt who is due to arrive from Brazil. The "aunt" (a wealthy widow) is supposed to seduce a judge and convince him to let his two nieces marry Charlie and Jackie before they're 25. Then the real aunt arrives. Hilarity Ensues.
  • In Hes My Girl, T. K. Carter dresses in drag so he can accompany his best friend on a trip to Los Angeles.
  • In The Hobbit: The Battle of the Five Armies, Alfrid hides among the women and children disguised as a woman to avoid joining the battle. The women decide to pick up weapons and join their husbands, and he still refuses to help, making him look even more pathetic.
  • I Was a Male War Bride is a Very Loosely Based on a True Story 1949 movie wherein French army captain Henri Rochard (Cary Grant) must disguise himself as a nurse in order to accompany his US Women's Army Corps wife back to America after World War II.
  • In Like Flint - Flint's boss Kramden tries infiltrating a woman-run organization in a very unconvincing drag disguise.
  • James Bond:
    • Thunderball opens with Colonel Bouvar, an adversary of Bond's, faking his death and dressing as his widow.
    • Diamonds Are Forever has Blofeld leaving his casino/hotel base disguised as an old lady.
  • In Lady in Cement, Tony goes to meet his pal Rubin, who is a vice cop, while Rubin is undercover as a woman as bait for a mugger who is targeting hookers.
  • The Little Rascals: Alfalfa and Spanky in ballerina drags. Bullies Butch and Woim find them quite attractive.
  • Lost in a Harem: After fleeing the palace, Peter somehow disguises himself as a woman (and Harvey as a baby) to avoid Nimativ and his guards. Unfortunately, Nimativ manages to see through the disguise. Later, Harvey disguises himself as Teema, one of Nimativ's wives, to distract him while Peter steals the hypnotic rings.
  • In Love Exposure, the protagonist Yu loses a bet and must crossdress in public, kiss a pretty girl, and tell her he loves her. This is also what sets off the bulk of the film's plot.
  • Mabel's Blunder: Mabel's brother puts a veil over his face to complete the disguise.
  • Mexican Hayride: After escaping from nearly being arrested, Bascom encounters the same police the next day while disguised as an old Mexican woman running a food cart, and ends up helping get Lambert away from the cops so that he can help Bascom retrieve the money that Dagmar stole from him.
  • Mr Headmistress involves a thief (played by Harland Williams), who just got out of prison and is being chased by a bunch of thugs who want him to pay off a very large debt. While escaping on a train, he accidentally runs into a middle-aged woman and takes her luggage. He escapes from the thugs by dressing as her, which causes him to be mistaken for a new headmistress about to take charge of an all-girl boarding school. Not only does he have to keep his Number Two, the teachers, and the students unaware of his identity, but he has to find a way to pay off the bad guys, so they stop looking for him. Naturally, Hilarity Ensues. At the end, after the ruse is discovered and the bad guys are arrested, he is invited to stay on as the first headmaster.
  • Mrs. Doubtfire: A divorced father played by Robin Williams dresses up as a British housekeeper to stay close to his children.
  • The killer disguises himself as a woman to evade the police cordon in Night After Night After Night.
  • Nighthawks: DaSilva has a penchant for this. In an early scene, he disguises himself as a woman to lure in some muggers. During the finale, he ambushes and kills Wulfgar while pretending he's his wife, who Wulfgar's targeting in revenge for DaSilva foiling his terrorist plot.
  • Freddy Krueger does this in A Nightmare on Elm Street 4: The Dream Master. When Kristen falls asleep in the school nurse's office, Freddy disguises himself as the nurse to mess with her, before reverting back to his nightmare form.
  • In The North Avenue Irregulars, Rose doesn't drive so her husband Delaney agrees to drive for her, reluctantly dressing in drag so The Mafia doesn't recognize him.
  • Nuns on the Run combines this with Bad Habits.
  • The Olsen-banden series and its Norwegian & Swedish Foreign Remakes feature this trope a few times, justified by the protagonists' penchant for using disguises in general to aid in their heists:
    • Kjeld dresses up as a maid in Olsen-banden på spanden, introducing himself as "the young girl who cleans the room".
    • Egon takes on the role of a maid (naturally called "Egonne") at one point in Olsen-banden over alle bjerge.
    • Egon's counterpart from the Swedish adaptions (coincidentally nicknamed the traditionally female name "Sickan" by his compatriots) does this thrice in total:
      • In Jönssonligan får guldfeber, his henchman Vanheden suggests that Sickan should "be a madame" so they can distract their mark better. Sickan starts out vehemently opposing the idea, but changes his mind when Vanheden tells him he has the legs and height to pull it off. Due to his lack of fitting clothes and inexperience with makeup (which Vanheden had to help him with after he tried to paint his glasses with mascara), it's implied that the disguise only worked due to the mark's poor eyesight.
      • In Jönssonligan på Mallorca, both Sickan and Harry dress up as old ladies when scouting another mark's house. While Sickan manages to pull it off well enough this time that Harry's partner Doris gets tricked by it later, "Harriet" doesn't even bother with any Larynx Dissonance.
      • Finally, Sickan dresses up as an old (supposedly German) woman again in the licensed game Jönssonligan: Jakten på Mjölner while trying to pass through his nemesis' outdoor party unrecognised. Despite Doris falling for it the last time, she is the only NPC to see through the disguise this time — and the only one to complain about it if you interact with her.
  • In One, Two, Three, Right-hand man Schlemmer disguises in Sexy Secretary Ingeborg's dress to fool the Russians, so they'll let Otto free.
  • In On The Double Danny Kaye tries to hide from a couple of Nazi officers by disguising himself as a female nightclub singer.
  • In The Outlaws IS Coming!, Larry and Curly Joe disguise themselves as women to escape from the showgirls' room in the hotel.
  • In Paddington (2014), Mr Brown disguises himself as a female cleaner to infiltrate the Geographer's Guild.
  • Pee-wee's Big Adventure: Pee-Wee quickly pulls together a drag masquerade while approaching a police roadblock, playing wife to escaped convict Mickey. It's not much of a disguise - just Pee-Wee in a chenille housecoat - but it fools the police and gets a squicky leering gaze from Mickey. Toward movie's end, Pee-Wee also dresses as a nun to sneak onto a movie set and reclaim his bike.
  • A young Germanic woman named Johanna in the 2009 film Pope Joan disguises herself as a man after her village is sacked by Vikings. She joins a Benedictine monastery as a monk. Forced to flee when she becomes ill Johanna abandons her disguise while working for Arn - the son of a woman she had helped several years ago. Resuming her disguise Johanna travels to Rome, where she comes to the attention of the Pope.
    • Years later, Arn’s daughter Arnalda disguises herself as a man named Arnaldo and eventually becomes a Bishop.
  • Bob Hope does this in The Princess and the Pirate in order to avoid being chucked overboard by said pirate.
  • Private Resort - Ben (Rob Morrow) does this when he and Jack are trying to get away from the Maestro (Héctor Elizondo), who also ends up flirting with him, thinking Ben is a woman.
  • The twist in Psycho, of course, is that Norman Bates was disguised as his late mother while committing murders. What's so strange is that he was framing his "mother" personality for the killings.
    Norman's mother: "He was always bad. And in the end he intended to tell them I killed those girls, and that man, as if I could do anything, except just sit and stare, like one of his stuffed birds."
  • Revenge of the Pink Panther - Clouseau picks up someone he thinks is a woman, but is a criminal known for his female disguise. He forces Clouseau to exchange clothes and takes his car...Clouseau is subsequently picked up by his fellow police, and he unnecessarily explains "Do not let my legs fool you, I am really a man!"
  • A long haired male member of the gang is dressed up as Vito's wife to lure Vito into an ambush at the hostage exchange in Revolver (1973).
  • In The Ribald Tales of Robin Hood, Robin escapes from his cell by disguising himself as Marian.
  • In Robin Hood: Men in Tights, the Merry Men dress in drag to get into the castle before the marriage of Rottingham to Maid Marian (or Robin's hanging, either way it's a party), complete with Little John keeping his obvious full beard. Afterwards, Ahchoo remarks, "Let's get out of this ladies’ clothing and get into our tights!"
  • In The Scarlet Claw, the killer leaves Judge Brisson's housekeeper Bound and Gagged and takes her clothes in order to get close enough to the judge to murder him.
  • The earlier Wayans' film Scary Movie uses this for a gross-out gag with the high school sports coach "Ms. Mann", a very muscular guy who is pretending to be a woman so he can get closer to the students. This becomes obvious when Cindy goes to her for advice and sees a set of balls hanging out. (The person who played "him", by the way, is in fact a woman, just one who has obviously been abusing steroids).
  • Martial Arts of Shaolin starring Jet Li (again!) Jet and his best friend take turns disguising themselves as shepherdesses to sneak through a checkpoint while avoiding Manchu guards.
  • In Sherlock Holmes (1932), Holmes goes to visit Alice's father disguised as his 'Aunt Matilda'. The disguise is good enough to fool Moriarty who opens the door for 'her' as 'she' leaves the room.
  • In Sherlock Holmes: A Game of Shadows, Holmes makes use of the paper-thin disguise variation. Mainly for laughs.
  • The two male protagonists do this in the film Ski Party, and it's even noted by one of them that they're "play[ing] Some Like It Hot".
  • In Some Like It Hot, Jack Lemmon and Tony Curtis play small-time jazz musicians who end up accidentally witnessing the St. Valentine's Day Massacre, which puts them in danger from the mob. They have to get out of town as quickly as possible, but the only train leaving town any time soon is transporting an all-woman jazz band. Jack and Tony dress up as women in order to join the band and board the train to Florida, and hilarity ensues.
  • The film Sorority Boys, where three frat boys Drag it up and join a rival sorority. Thanks to Attractive Bent-Gender, one of the boys' admirers is the sorority's bisexual president.
  • Jackie Chan during his cameo in Super Cop 2 have him dressed in a blouse, wig, and fake boobs while spying on an informant. He even had a Hammerspace between his legs to store his holster! Chan is the one in red, btw.
  • In Tango & Cash, Cash (played by Kurt Russell), dresses in drag in order to exit a nightclub without the cops becoming suspicious. Cue Russell's male and female fans screaming in horror...
  • D'Artagnan in The Three Musketeers (2011) is forced to escape Milady by dressing in her maid's clothes. Judging from Athos' manservant's reaction to him, he wasn't half-bad as a woman.
  • Used quite often in The Three Stooges. Especially blatant in these cases because most of the Stooges not only have very obviously male faces but are... well, exceptionally ugly, even as men. Also, Curly, the largest Stooge, is the one who most frequently has to do this. In fact, in one episode, Curly dresses up as a female Native American to fool a French hunter, who actually goes so far as to marry this "fat Indian momma" and take him/her to his bedroom. Hilarity ensued, although the disguise was revealed before anything truly unfortunate could happen.
  • Titanic (1997): In a deleted scene, Officer Lowe finds one man hiding underneath a blanket, pretending to be a girl in his lifeboat. This was based on testimony from Lowe and Daniel Buckley (the young man from steerage who pretended to be a woman). Interestingly, every adaptation has featured at least one man dressing up as a woman to escape the sinking ship.
  • Tootsie: "Dorothy Michaels" becomes quite the man magnet, in fact. His/her own pursuit of a female costar is kind of complicated.
  • In Total Recall (1990), Douglas Quaid tries to infiltrate Mars undetected by disguising himself with an animatronic "fat woman suit".
  • Trick or Treats: Malcolm manages to get out of the hospital buy stealing a nurse's uniform and dressing up in it, while also putting on a wig and lipstick.
  • At the start of Under Ten Flags, the Horny Sailors on a British merchant ship are eagerly checking out the kimono-clad women on a (then still neutral) Japanese vessel, until the 'women' cast aside their fans and parasols and race to man the guns of their disguised German raider.
    First Mate: They're not girls, they're not even Japs—they're Germans!
  • Up Pompeii films:
    • In Up Pompeii, Scrubba switches clothes with Lurcio in order to allow him to escape the condemned cell.
    • In Up the Chastity Belt, Lurkalot and Sir Coward disguise themselves as women in order to unionise the Bedlah Babes and encourage them to stage a Lysistrata Gambit.
    • In Up the Front, the Buttercup Girls dress Lurk in Isobella's clothes in order to help him hide from Colonel von Gutz.
  • Watch Your Stern: When Miss Potter is due to arrive at the HMS Terrier, Blissforth is disguised as her, so the destruction of the Creeper torpedo plans won't be found out. When the real Miss Potter arrives, she is herself mistaken for a spy in disguise as a woman.
  • The Wayans Brothers' film White Chicks, where they're not only disguising their sex but their race as well. One even ends up with a Scary Black Man as an admirer.
  • In the 1975 film The White The Yellow The Black, all three main characters do this to rescue a village's women. Their cover is blown when the thugs tear off Black Jack's small veil covering his mustache, and a fight ensues.
  • John Candy is also seen dressed as a woman at the end of Who's Harry Crumb?.
  • In Willow, Madmartigan disguises himself as a woman in an attempt to hide from a woman's jealous husband. It backfires when said husband finds him attractive and proceeds to proposition him. Right in front of his wife.
  • In The Wing or the Thigh, Charles Duchemin disguises as an old lady to test out the quality of a restaurant without being spotted.
  • In Yamato Takeru (and similar to the original legend, see below), the titular character dresses up like a dancing woman in order to get close to the warlord Kumaso Takeru. The warlord isn't fooled, though.
  • In Yellowbeard, Gilbert tails Dan, Lord Lambourn, and Dr. Gilpin through Portsmouth disguised (somewhat unconvincingly) as a prostitute.

  • At one point in The Adventures of Huckleberry Finn, Huck dresses up as a girl to investigate what's been going on in town since he ran away. After an old woman tests him and eventually sees through it, he has to come up with a new excuse about why he's a boy dressed as a girl.
  • The Berenstain Bears Big Chapter Books: The Berenstain Bears at the Teen Rock Café features a rash of shoplifting at Bear Country Mall. In the climax, the thieves are revealed as a couple of old ladies... who turn out to be the Bogg Brothers wearing dresses and bonnets, using their dresses to hide the sacks of stolen goods they're smuggling out.
  • Bret King Mysteries: The Dragon in The Secret of Fort Pioneer commits an act of sabotage while disguised as a female extra in a western movie.
  • In A Brother's Price a male character disguises as a female prostitute. However, as men are rare in the setting, female prostitutes try to look like men, to appeal to their female customers, most of whom consider themselves heterosexual. Which means that he is a man, who disguises himself as a woman, who disguises himself as a man. Due to the gender roles in that setting, the appearance he is ultimately described as having is somewhat Drag Queen like.
  • Captive Prince: Laurent disguises himself as Lady Jokaste so that he and Damen can get past a patrol of soldiers aligned with Jokaste's lover. The leader of the soldiers in question is thoroughly convinced, and even comments on "Jokaste"'s beauty.
  • The Cat Who... Series:
    • One of the plotters in book #17 (The Cat Who Blew the Whistle) is revealed to be a man who had been masquerading as a woman. His name is Lionel, but he went by Lionella, or just Nella for short, in his disguise.
    • Discussed, but not actually done, in book #22 (The Cat Who Robbed a Bank). While he's discussing ways to secretly observe Delacamp's meeting with the ladies of Moose County to look over their jewelry, Qwill suggests sneaking in as a member of the wait staff; when told they're all young women dressed as French maids, he half-jokingly says that "If it weren't for my moustache, I could go in drag.", which earns a lot of laughs from his companions.
  • Terry Pratchett's Discworld:
    • In Jingo, after Fred and Nobby's Dressing as the Enemy scheme falls flat, they steal some costumes from a trio of traveling performers: "Gulli, Gulli, and Betti". Nobby gets stuck playing "Betti", an exotic dancer, and his quite homely appearance is explicitly cited in a footnote as being in a heated battle with the Attractive Bent-Gender trope. The trope loses. No mean feat in a world that runs on tropes the way RoundWorld runs on physics. Nobby actually enjoys his experience, to the point where when he goes on patrol to entrap unlicensed thieves targeting ladies of negotiable affection, he insists on playing the bait — even though he's partnered with Angua, who is not only strikingly beautiful but is tough enough to act as her own backup.
    • In Monstrous Regiment, The Squad is forced to dress up as men to join the army. So, as soon as they need to infiltrate a keep, the Lieutenant, utterly oblivious to the fact that he is the only actual man in the group, declares that he is the only one able to pass as a woman. He's actually right.
    • Escaping from prison disguised as a washerwoman is briefly mentioned in three books: In The Last Continent, Rincewind is going through all the standard escape tropes with a Genre Savvy guard and is disappointed to learn the washerwoman is said guard's mum. In The Last Hero, Contractually Genre Blind Evil Harry Dread has a jailer who's described as letting a bearded washerwoman in Incredibly Conspicuous Drag out of the cell without a second thought. And in Raising Steam, reformed conman Moist recalls visiting Quirm in a variety of different disguises, and once as a different sex. A footnote adds that the jailers didn't figure out how he escaped until they realised the laundry never came back.
  • In the Doctor Who Eighth Doctor Adventures novel The Book of the Still, Fitz is in a sort of Lotus-Eater Machine, whose creators are trying to come up with an interesting adventure scenario for him. He ends up marrying an evil, lecherous version of the Doctor, disguised in a Pimped Out Wedding Dress as Evil!Doctor's unwilling bride, then having a swordfight, rescuing his Girl of the Week, and flying around with a jetpack, still in the dress.
  • In Catherine Jinks' Evil Genius Trilogy, Cadel cross-dresses on multiple occasions and uses this trope to fool his teachers in the academy and to escape Thaddeus Roth as a female identity he calls Ariel.
  • Used very dramatically in the third Finnegan Zwake novel when Sheridan Shakespeare disguises himself as Nada Kloo.
  • In one of the Geronimo Stilton books, Geronimo's Arch Rival uses an Identical Stranger to gain ownership of his newspaper. Geronimo realizes he can use the same trick to get the newspaper back, and then he and his sister notice their cousin Trap is nearly identical to his Arch Rival except for two things: they have different color fur, and oh yeah, Trap is male and the Arch Rival, Sally, is female. After a day at the salon, Trap becomes the spitting image of Sally, and after a night of watching footage, he's able to mimic her voice flawlessly.
  • In the novel God Stalk, the protagonist (Jaime Kinslayer) was saved/adopted by a soft-hearted innkeeper named Tubain; while living at the inn, she occasionally heard Tubain being berated for his generous impulses behind closed doors by his wife Abernia, who never left her rooms. Not until the story is nearly over does Jaime learn Abernia's secret: She's Tubain in drag, yelling at himself.
  • Rochester does this in Jane Eyre. He's supposed to be Mother Bunches, a gypsy Fortune Teller. When "she" lets on that Rochester isn't as wealthy as he seems, Blanche gets upset. "She" seems to know so much about all the guests that Jane suspects "she" may be Grace Poole, and isn't too surprised to catch on that it's really her boss.
  • In Gary Jennings' The Journeyer, Marco Polo's clothes accidentally get burnt in a fire. The girl who does it offers him some of her clothes. He puts them on to avoid getting the girl in trouble.
  • J.P. Beaumont: As part of a scheme to frame a female singer in Taking the Fifth, the male killer dresses in one of her performance outfits of evening gown, High-Class Gloves, and long blonde wig to commit a murder: known that at a distance, that is all a witness will be able to identify.
  • The Last Binding: When the main characters magically disguise themselves for a dangerous mission at a party, they find the spell doesn't work properly on Alan Ross, so they dress him — a slight-figured Pretty Boy — very convincingly as a lady's maid instead.
  • In Last Call by Tim Powers, the protagonist dresses in drag to infiltrate a party being hosted by the villain. In defiance of the usual subtropes, nobody is in any doubt about his sex, let alone strangely attracted to him — but it serves perfectly as a disguise in as much as nobody suspects for a moment that it's him.
  • Looming Gaia: Homosexuality is illegal and punishable by death in Evangeline Kingdom. Gay men are known to disguise as women known as "miss Marys" ("merry" meaning gay men) to be able to live with their boyfriends.
  • Macdonald Hall: Elmer has to dress as a cheerleader for a whole football game for one of Bruno's plans in The Zucchini Warriors, something that Elmer's lack of athleticism and nearsightedness-the girl he's impersonating doesn't wear glasses- turn into a disaster. Elmer is quite unhappy about the whole situation and only consents to the plan after Bruno signs a contract giving Elmer the right to sit out any future misadventures Bruno drags the gang into.
  • In The Machineries of Empire short story Extracurricular Activities, Jedao ends up crossdressing to escape the Gwa prison, as the only person he knocks out whose clothes match his size is a woman.
  • In Malevil, there is Bèbelle. A Creepy Crossdresser who uses this trope to his advantage, he pretends to be a woman to infiltrate settlements, prior to his brigand army invading.
  • Moongobble and Me: In book 5, Moongobble (with help from Edward's mother) puts the Oggledy Nork in a dress to disguise him as an old woman. Astoundingly, it works, as the city guards of Flitwick City buy it when Moongobble claims the Oggledy Nork is his mother.
  • In the children's book Miss Nelson Has a Field Day, the principal, Mr. Blandsworth, tries the "Miss Viola Swamp" schtick on the school football team and fails spectacularly ("Oh rats! How can they tell?"), leading Miss Nelson to take matters into her own hands.
  • Bunny Manders disguises himself as a woman in one of the Raffles stories.
  • In the Rainbow Magic series, the goblins do this all the time, especially in the Fashion Fairies series. One Princess Fairy book has a goblin dressed as a princess, with the narration calling him Princess Goblina.
  • Rose of the Prophet: Mathew gets repeatedly mistaken for a woman and then forced to dress as one, which then becomes a disguise. This endangers his life later, since he's accused of attempting to seduce a man this way, which is a capital crime (but poor Mathew intended no such thing-he's actually asexual).
  • The Saga of Tuck opens with Tuck dressing as a girl for Halloween; the irony of this only becomes apparent later. Tuck soon befriends a large number of his girlfriend's friends, but must keep crossdressing since their parents only trust him because they believe that he's a girl. Then it turns out that a lot of them, his girlfriend included, prefer his female persona. Then he gets a job as a babysitter from a woman who thinks he's a girl. Eventually, he actually finds out that he's a late-blooming hermaphrodite, which is the reason he has started being called "miss" even when he's not crossdressing.
  • In Shadow Magic, the sequel to Havemercy, Mamoru, the prince of the Ke-Han, is on the run with his retainer Kouje after his brother framed him for a crime. Reasoning that the guards would be looking for two men on the run together, the pair decide to disguise Mamoru as a woman. Mamoru being a Pretty Boy, it works, though one performer they meet manages to see through them.
  • Sherlock Holmes at one point disguises himself as an old lady for the purpose of tailing a suspect, who kindly picks up his parasol for him. He's also (temporarily) fooled by a man in drag in A Study in Scarlet.
  • The Sherlock Holmes Stories of Edward D. Hoch: In "The Adventure of the Domino Club", Miss Sarah Rutherford infiltrates the all-male Domino club wearing male evening dress and the hood and mask all attendees are required to wear. Her disguise is excellent, but no match for Holmes' powers of observation.
  • Small World (Tabitha King novel) opens with Roger in very detailed drag as he attempts to steal the Princess Dolly painting from a museum.
  • The Thinking Machine: In "Convict #97", two brothers perform a Twin Switch. The innocent twin enters his brother's cell disguised as their (non-existent) sister. In the cell, the brothers swap clothes, and the convict exits in the 'sister's' garb.
  • In Wet Magic, Reuben runs away to look for his biological parents. Mavis brings him one of her outfits as a disguise. He doesn't have to wear it for very long before the children are taken to the Merkingdom, where they all wear seaweed clothes.
  • In The Wind in the Willows, Toad escapes from prison disguised as a washerwoman. Later on, he blows his own cover when a barge-woman insults his washing abilities and his pride can't take it.
  • In The World According to Garp, Garp dresses as a woman to attend his mother's funeral.
  • Played for Laughs in the X-Wing Series novel Starfighters of Adumar. Wedge's plan for escaping pursuit in an urban environment involves a camcorder, a truck, "and four sets of Adumari womens' clothing".
    Hobbie: Boss, tell me you're not putting us in women's clothing.
    Wedge: Very well. I'm not putting us in women's clothing.

    Live-Action TV 
  • Johnny Depp's attraction to eyeliner didn't start with Captain Jack Sparrow. Way back during 21 Jump Street, he was undercover in drag in "In the Custody of a Clown" and looked far too convincing.
  • Used in one episode of 3rd Rock from the Sun where Dick dresses as a woman to infiltrate a woman's discussion group his love interest Dr. Albright was attending. Needless to say, Hilarity Ensues.
  • In The Adventures of Superman episode "Double Trouble", one of the crooks disguises himself as a woman to get through customs.
  • 'Allo 'Allo! is full of it. Men dress up as flamenco dancers, nuns and Resistance girls, while women pretend to be errand boys or carters. At one point Maria complains about not being allowed to disguise as a small girl, to which Michelle responds that she is a small girl.
  • On Arrested Development, Tobias dresses up as a British housekeeper in order to spend more time with his daughter. Absolutely nobody is fooled by his disguise. The narrator acknowledges that this is a direct rip-off of Mrs. Doubtfire, with a little Mary Poppins thrown in.
  • This was the premise of the short-lived Fox sitcom Ask Harriet, where the main character, Jack Cody, dresses up in drag to work at a company whose boss is only looking to hire women.
  • Murdock does this in the fourth season of The A-Team; in order to get past an angry mob that has the rest of the team holed up, he dresses as a pregnant woman and convinces them that "One of the men in there is the father of my baby!"
    • In "Till Death Do Us Part", Murdock poses as the bride at a wedding while the rest of the team help the real bride escape.
  • On Barney Miller, each member of the squad ends up going undercover in drag:
    • Sgt. Dietrich is good-humored about it but doesn't realize that he isn't fooling anyone and just ends up embarrassing himself.
    • Harris, after reluctantly shaving off his mustache, dolled himself up in characteristic style and was fairly attractive.
  • Big Time Rush has multiple examples:
    • Logan does this thrice. Oh, and one time he's hit on, and the third time the situation is used to help James write a love song.
    • James does this himself in the prom episode.
  • Blackadder Goes Forth:
    • In the episode "Major Star", Lieutenant George develops a drag act as part of an attempt to boost troop morale, and 'Georgina' promptly attracts the amorous attentions of General Melchett, which "she" only escapes by faking "her" death. A revived drag act featuring the General's driver, Corporal Parkhurst, is dismissed by Melchett as completely unconvincing — even though Corporal Parkhurst is really a woman.
    • Earlier, in the episode "Nob and Nobility" in the third series, the Scarlet Pimpernel disguises himself as Madame Guillotine, a female French Torture Technician, in order to rescue Edmund and Baldrick from French revolutionaries. This ends badly for him as Edmund poisons him before finding out that he's an ally.
  • The TV series Bosom Buddies was an early 1980s sitcom where two men (Tom Hanks and Peter Scolari) disguised themselves as women to get a New York apartment.
  • Occurred at least twice on Boy Meets World:
    • In "Chick Like Me", Cory Mathews is convinced to write something more meaningful for the school paper than his usual bad jokes column. After the class begin discussion of "Black Like Me", an account of a white man's experiences disguised as a black man for a week, he decides to disguise himself as a girl so he could discover how different their experience of high school life was from that of a boy. Having failed to become very feminine, Shawn tries to demonstrate how to do it. They end up finding out that Shawn is a Wholesome Crossdresser in the closet but for the purposes of this episode he is Disguised In Drag, even going out on a date with a boy who doesn't know that he's a boy too, for the purposes of research. Since the episode revolved around sexual harassment, it doubled as a Very Special Episode, ending with Shawn getting a date with a girl he liked because she knew that he now knew what it was like to be the "chick" on a date.
    • In "What A Drag!", Jack and Eric dress up as women to avoid the vengeance of a badass who they tried to have arrested. Once again, they turn to Shawn for advice and he provides spot-on tips for crossdressing. By the end, Eric decides to give it a try on a more regular basis, just to "Keep in touch with my feminine side."
  • One episode of The Closer had a suspect disguised as his girlfriend to throw off the cops. He uses it for working on a cruise ship. The disguise is so good that Det. Sanchez was flirting with him and kissing him. Sanchez went to therapy after that.
  • Cory in the House: Cory dresses up his sister Raven for a White House uniform presentation.
  • In one episode of A Different World, Dwayne Wayne and Ron Johnson have to dress as women to hide from cocaine dealers who are pursuing them.
  • In CSI: Miami, A group of robbers disguise themselves in drag—but as it turns out, there's an extra level of their disguise: They're actually women, who have decked themselves out to appear as men dressing as women. As one character puts it: "Women... disguised as men disguised as women."
  • Danger 5: Pierre in a corset and blond wig in "Fresh Meat for Hitler's Sex Kitchen". Without covering up his moustache, naturally.
  • Dead Man's Gun: The eponymous character when sneaking out of town at the end of "The Womanizer" which leads to a possible Black Comedy Rape ending when the stage he's on is robbed by outlaws who find him attractive in his disguise.
  • The Third Doctor dresses as a washerwoman in the Doctor Who serial "The Green Death". It was just convincing enough to fool an unobservant guard who wasn't looking at him and to pass a message on to Captain Yates ... who promptly began to rib him about it.
  • The Due South episode "Some Like It Red" (a Shout-Out to Some Like It Hot, referring to the "red" of Fraser's Mountie dress uniform) has Fraser going undercover as a teacher in a Catholic girls' school. In drag, he bears an uncanny resemblance to Lucy Lawless, so obviously he fits Attractive Bent-Gender as well. The most interesting point is that the actor, Paul Gross, managed to portray a lot of feminine mannerisms in addition to wearing the disguise itself. Straight and gay fans of both genders have confessed to confused feelings for "Ms Fraser".
  • Farscape
    • Played for Laughs in "Coup by Clam", where John Crichton and Rigel dress as women in order to infiltrate a brothel. Crichton gets hit on by a government thug who, in an interesting subversion, already knows that he's a man dressed as a woman as he'd seen Crichton earlier. Also, Rygel doesn't bother to shave his beard (perhaps female Hynerians have facial hair as well) and appears to be wearing a wedding dress.
    • "Different Destinations" had it go horribly wrong when Crichton tried to smuggle a captured general out of the defender's camp in woman's clothing so he could negotiate a ceasefire. They get caught and the general is shot by a fanatical defender. His army then finds the body dressed like one of the enemy's women and conclude it was a deliberate insult, scuttling any chance for peace.
  • Father Brown: In "The Company of Men", the killer Moira created a fake identity as the elderly Colonel Partridge who could sit in the club all day and not be noticed.
  • An episode of Forensic Files had detectives confused about the timeline of a victim's murder—her body was found in her backyard, but multiple witnesses swore that they saw her leaving for work. They eventually learned that her killer had planned the crime so far in advance that after killing her, he dressed in her clothes and donned a wig, thus enabling him to avoid detection and dupe her neighbors into thinking that they'd seen her.
  • The finale of Gilligan's Island sees Mr. Howell, the Skipper, and the Professor trying to pass as women in order to fool the natives into thinking they're goddesses. Gilligan turns out being the only one able to dupe them, and, naturally, Attractive Bent-Gender ensues.
    • Gilligan himself gets roped into this more than once, punctuated by a Gilligan Cut.
  • After raping Lucy Cooper, Guiding Light's Brent Lawrence faked his death to avoid prosecution, then returned to town disguised as a woman named Marion Crane in order to befriend her and continue stalking her. Not until he kidnaps her and removes his disguise does she have any idea who he really is.
  • An episode of Hercules: The Legendary Journeys has Autolycus and Salmoneus do this as a Whole-Plot Reference to Some Like It Hot. Bonus points for featuring Michael Hurst as The Widow Twanky.
  • In an episode of Hogan's Heroes, Newkirk attends an officer's wives party like this, as he's impersonating a spy whose regular MO is this. Every Allied main but Kinch has cross-dressed at least once—Hogan, Newkirk and LeBeau in "I Look Better in Basic Black", and Carter in "Reverent Kommandant Klink" (that one was for stage purposes, not espionage). Besides the aforementioned officers' wives party, Newkirk gets in drag in at least three or four episodes.
  • iCarly: In "iWant My Website Back", Spencer disguises himself as a "busty old woman" and an old man gets the hots for him. Even after Spencer blew up his cover that he is really a man, the old geezer still pursued him to his apartment, willing to "start all over again" as long as Spencer wears back the wig.
  • In the Pilot of It's Awfully Bad for Your Eyes, Darling..., Bobby is disguised as one of Samantha's female flatmates to stop her mummy from meeting him.
  • The Jeeves and Wooster episode "The Delayed Arrival" has both Jeeves and Bertie briefly in drag; Jeeves disguised as an American author, and Bertie as a maid.
  • In Kamen Rider Double, the Liar Dopant is lured to an auditorium by Wakana claiming she wants to meet him. Ryu and Akiko dress as Wakana's (male) bodyguards and Philip dresses up as Wakana herself. Akiko is bewildered by how convincing a woman he makes, having been completely fooled until the reveal, and the gender confusion causes her to faint.
  • There have been three male contestants on King of Mask Singer who have participated under a feminine pseudonym. All three were good enough to advance to round two; and they were all so convincing that when they revealed their true identities, the panellists were very surprised.
  • LazyTown: Robbie disguises himself as "The Birthday Fairy" and "Miss Roberta". You can also see a variety of ladies' dresses in Robbie's disguise chambers that he has yet to wear.
  • In The Legend of Dick and Dom, the heroes need a potion ingredient from a vampire... Alan, The Vampire Baby. Prince Dom is dressed up as a nanny with giant feeding bottle to try and get close to him.
  • In The Love Boat, Julie and Isaac have Gopher dress up as an old lady and get Captain Stubing to help "her" with "her" luggage to make the captain look good to the cruise line's new owner. Their scheme meets with little success.
  • This trope does not, as a general rule, apply to Jamie Farr's character, Max Klinger, on M*A*S*H. Klinger merely crossdresses in an attempt to make people think he's crazy, so that he can get a Section 8 psychiatric discharge. However, there are isolated exceptions over the show's long run:
    • Klinger does disguise himself as a woman "for real" in the later-season episodes "Private Finance" and "Taking the Fifth", as well as in an episode of AfterMASH. He also disguised himself as a Korean woman (with a straw hat pulled down over his face) during the episode "Dear Peggy" so he could sneak out of camp. This failed when Colonel Potter recognized him: "Korean women are not noted for hairy knuckles."
    • In one episode, the only way the 4077th crew can help a South Korean deserter is by disguising him as a woman. Who do they go to for advice? Klinger. He looks the man up and down for a second, then says "Size 9, junior miss," and instantly picks the perfect dress for him to wear from his own clothing rack.
  • In one episode, the boys of The Mighty Boosh disguise themselves as old women to infiltrate a bingo hall in search of a demon granny they'd accidentally summoned. Hilarity ensues, especially seeing as Howard doesn't even shave his mustache
  • The Monkees did it twice. In the episode "The Chaperone," Davy's love interest can't attend a party without a chaperone, so Micky dresses as a woman who's chaperoning the party. The girl's father ends up being attracted to him. In "Some Like it Lukewarm," Davy dresses as a girl so that they can enter a band contest for mixed-gender groups. Naturally, the guy running the contest falls for Davy.
  • In Merlin (2008), Gwen disguises Sir Leon as a female courtier to escape Camelot. While it's mildly Played for Laughs, we never really get to see the finished disguise.
  • A tip for escaping from prison in My Name Is Earl: if you're going to disguise yourself as a nurse, make sure you don't look too attractive.
  • invokedAstoria, Waldorf's wife, from Episode 13 in Season 4 of The Muppet Show looks exactly like Statler in drag. There isn't really any suggestion that it is Statler, but for those with Ho Yay theories...
  • Murder, She Wrote: In "The Great Twain Robbery", the murderer sneaks up on what would be his next victim, only to discover it is a male police officer disguised in drag.
  • In the second episode of MythQuest, Thor show Alex!Vali what happened the last time his hammer was stolen: He dressed up as his wife, whom the thief wanted to marry, and sat through a wedding feast before revealing his identity.
  • In the My Two Dads third-season episode "Kind of a Drag", Michael posed as Joey's wife to get rid of a pesky woman and accidentally became the object of desire for one of Nicole's male teachers.
  • In the season three Halloween Episode of NewsRadio, Davenote  dresses as a woman for the annual Halloween party. He comments on how depressing it is to learn at 30 that he looks better as a woman than as a man. Even funnier is when Lisa complains that he's wearing her dress — and it looks better on him.
  • Our Miss Brooks: In "The Stolen Wardrobe", Mr. Conklin, Mr. Boynton, and Walter Denton are falsely accused of robbing Sherry's Department Store. They end up (reluctantly) disguising themselves as women to evade the police.
  • Psychopath Diary: Dong-sik dresses as a woman after escaping prison.
  • Radio Enfer:
    • During the Halloween Episode, the members of the radio crew have to disguise as each other. Carl is the one forced to dress like Maria, much to his displeasure.
    • Another episode has Jean-Lou putting on a dress to participate in a personality contest. Although in this case, he had no idea that only girls were allowed to participate until being told by Carl.
    • One episode has Carl and Vincent do that to infiltrate a girls-only reunion.
    • Jean-David and Germain do this in order to help out with Maria's new job at a fashion boutique by pretending to be customers.
  • On Sanford and Son Fred learned the new hot tenant at his motel Sanford Arms he has the hots for was a high-end fence. Through obvious means he gets him to confess, but the undercover cop staying at his house dismisses it due to the obvious legal matters. Best friend Bubba manages to successfully bust the crook by cross-dressing, winning the thousand-dollar reward Fred and even Lamont were desperate for.
  • Saturday Night Live mines a lot of comedy from this vein. In one digital short, Keenan Thompson (a rotund black man) plays Reba McEntire (not a rotund black man). For the first verse or so, the gag is a fairly simple crossdressing bit. Around the start of the second verse, however, Thompson reveals that, in the skit, he actually is a man dressed as a woman (he does this by bluntly saying "And a penis!" when Andy Samberg sings about all of "Reba's" great attributes). Thompson spends the rest of the song explaining that he found a red wig in a dumpster and Samberg confused him with Reba. He says all of this with Andy standing right next to him. Andy doesn't seem to hear.
  • This happened a couple of times in Saved by the Bell.
    • Screech had to infiltrate the girls' locker room as an old Irish cleaning woman to record their singing.
    • Zack decided to dress in drag and watch his friends react to his tape announcing that he's going to military school. Nobody was fooled by the disguise.
  • Servant of the People: In season 2, when Vasiliy and Yuriy need to escape a group of thugs from the Journalists' Union, they disguise themselves as drag queen Verka Serduchka and her "mother".
  • Sister Boniface Mysteries: Combined with Bad Habits in "My Brother's Keeper", when Sister Reggie hides her brother Alfie, who is on the run from the police, in the convent by dressing him in a nun's habit.
  • So Awkward: In "Girls & Boys", the girls are mistaken for boys when dressing up for drama, and Lily keeps up the pretense in order to get closer to Matt. Ollie, without his contact lenses and trying to avoid wearing his old glasses, strikes up a friendship with Lily's alter ego 'Liam'.
  • In Some Assembly Required Jarvis, Bowie, Knox and Aster do this at least once. Although it's Played for Laughs Piper is often assumed to be this, usually as an insult by Aster or genuinely by every one else.
  • Used (somehow) completely straight in Star Trek: Deep Space Nine, where Quark has to undergo surgery to become a woman in order to impress someone who can restore an ally of his to power. Every aspect of this trope is invoked, so much so that even his brother finds him attractive, plus the actual subject of the ruse. This is partially justified because obviously Ferengi have different standards of beauty than humans and it's possible that Quark might be an attractive one after all.
    • And yes, the "crossdressing" does require surgery, but this is Star Trek, where apparently any disguise is done with extensive surgery. On the other hand, since this is Star Trek, "extensive surgery" equates to waving a coloured bulb over the patient's stomach.
  • InThe Suite Life of Zack & Cody, Cody disguises himself as a girl to enter a Beauty Contest in order to win the prize money and buy bikes for him and Zack.
  • The fourth episode of the series Sun Trap has Woody dressed as a female croupier so that he can investigate the disappearance of a large amount of money from the local casino. It is unnerving how brazenly he flirts with one of the customers, who fortunately doesn't realize.
  • In one episode of The Sweeney a character played by Warren Mitchell escapes from villains by dressing up in his girlfriend's clothes and a wig. Regan and Carter turn up. "Ooh Mr Wardle, you do look nice!"
  • Jack did this a couple of times on Three's Company. In one, he thinks the authorities are after him and dresses up as a woman (he claims to be Chrissy) to get past them. In a later episode, he entered a recipe contest as "Grandma Tripper" and dressed the part when he's selected as a finalist.
  • The guys from Top Gear did this using Syrian-style burqas during the Middle East Special because the current political situation meant that having it be known they'd gone from Syria to Israel even after passing through Jordan might cause them to be denied entry. As usual for Top Gear, it was Ambitious but Rubbish, as they found when they arrived in Damascus.
    May: [sees "Welcome Top Gear" sign on hotel] I've appeared on television, in drag, for nothing!
  • In a To Tell the Truth round involving a Tupperware Lady, one of the imposters was a woman disguised as a drag performer. And then very next round proceeds to invert this trope by having one of the imposters be the Tupperware Lady from the previous round out-of-costume.
  • One sketch by The Two Ronnies has them as stuffy commuters, who arrive at their station and chat about everyday topics, as they change into flamboyant ladies' outfits. The punchline: They're doing it because the station only has a ladies' lavatory.
  • The short-lived 1960s sitcom The Ugliest Girl In Town involved a guy masquerading as a female fashion model in London.
  • The episode "Beck Falls For Tori" in Victorious, Tori is terrified of doing a stunt in a movie, Beck does it for her by dressing in her same outfit, which he does, oblivious to the rest of her friends and the movie crew.
  • Wonder Woman: In "Death in Disguise", Starker was an enemy agent disguised as a woman, played by female impressionist Charles Pierce.
  • The short-lived 2011 sitcom Work It has two male ex-autoworkers disguising themselves as women in order to land jobs as sales reps for a pharmaceutical company. Incidentally, its cancellation after 2 episodes may have had something to do with the transgender rights groups protesting the show.
  • In the Young Blades episode "The Invincible Sword," Siroc dresses as a woman so he can disguise a bomb, made out of a watermelon, as a pregnant belly. It Makes Sense in Context, mostly.
  • Young Dracula: Eric van Helsing. He doesn't even bother to shave first, for chripes' sake.

  • In Clint Black's music video for "Summer's Comin'", Howie Mandel's character tries to befriend some women on a beach, but all of them turn out to be guys wearing blonde wigs (as played by Jay Leno, George Kennedy, Charlie Chase, Gerald McRaney, and Dick Clark).
  • *NSYNC's music video for their song "U Drive Me Crazy" had them disguise themselves as the Spice Girls in an attempt to get the attention of a music executive. It crosses over into Incredibly Conspicuous Drag because Joey Fatone and Chris Kirkpatrick were still sporting facial hair.
  • The folksong Patrick Street (and several variants) feature a sailor forced by circumstances to wear women's clothing.
  • Queen's video for "I Want To Break Free" has the guys all dressed as women, and is a homage to the British TV show Coronation Street.
  • The cover of The Rolling Stones' 1966 single "Have You Seen Your Mother, Baby, Standing in the Shadow?" has five airplane stewardesses who are really the Stones themselves.
  • Evillious Chronicles:
    • At the end of "Servant of Evil", Allen dresses as his sister to save her from execution.
    • In "The Lunacy of Duke Venomania", Karchess Crim disguises himself as a woman in order to rescue his lover from the mad duke's harem. It works, and he reveals himself after stabbing Venomania with a poisoned blade.

    Myths & Religion 
  • Norse Mythology: In the Poetic Edda ("Thrymskvida"), Thor disguises himself as the fertility goddess Freyja in order to retrieve his hammer after the king of the giants steals it, and demands her hand in marriage in exchange for its return. Being part of an oral tradition, Hilarity Ensues quite often in the retellings as Loki, playing the part of "Freyja's" chaperone, has to maintain his cover by coming up with increasingly convoluted explanations for why the dainty, feminine goddess can eat a cow, drink a barrel of mead, has a beard, and so forth.
  • In Greek Mythology, Achilles is disguised as a woman due to a prophecy that stated he would die if he went to war. Versions of the myth differ from place to place, but the basic story is he's shipped off to live with the daughters of Lycomedes, king of Skyros, under the name Pyrrha (the red-haired girl). When Odysseus comes looking for him after learning that Troy would not fall without him, he goes to Skyros under the guise of a peddler. He tricks Achilles by laying out perfumes and such, which the daughters all go crazy for, and weapons, which Achilles goes for, instantly blowing his cover. RWBY references this by using this as the basis of Pyrrha Nikos (with similar basis for her three teammates in Team JNPR).
    • In another version, he doesn't disguise himself but brings gifts for all the king's daughters, a sword and spear having somehow found their way into the collection of jewelry and trinkets. Then an alarm is sounded, and Odysseus sees one of the daughters instantly take up arms while the others run around in a panic.
    • The Achilleid's rendition of the myth explains that a muscular soldier like Achilles manages to pull off this facade because of his natural beauty and his mother's instruction on how to move like a woman.
  • Prince Yamatotakeru, a semi-legendary figure in Japanese Mythology, was said to have dressed as a maidservant to kill members of a rival clan.

    Pro Wrestling 
  • Rikishi disguised himself as a woman when Eric Bischoff went looking for a lesbian to hire and send after Stephanie McMahon. Bischoff would later use an old man disguise in 2002 for a Smack Down appearance involving the tag team of Billy and Chuck, which was being portrayed in a similar manner to the earlier plan.
  • Macaela Mercedes's personal referee, Whipme Spearz, became such after Mercedes found he was trying to pass himself off as a woman so he could compete for PGWA and GLORY and became her lackey to prevent being outed.
  • Stevie Richards in WWE after Victoria inexplicably stopped being a psychopath and went back to her goofy dancer gimmick. She didn't want anything to do with him suddenly, because Ricards was still crazy, so he started following her around, ruining Victoria's matches when in plain clothes but aiding her while disguised as a woman.
  • Trent Barreta as "Girl From Mexico" in his attempt to win the FCW Divas Championship after the company was revived by WWE.
  • Santino Marella and Beth Phoenix's relationship became strained when Santino began disguising himself as his "sister" Santina, so "she" could win the Miss Wrestlemania crown.

  • In The Gungan Council, C'orringath Ven'Traas and Ayin Kaes looked great as handmaidens for the queen of Naboo.

  • In the sci-fi comedy Babes from Outer Space the heroes are in a Lady Land, so naturally the Dressing as the Enemy trope involves this trope as well.
  • Brandon Thomas' 1892 farce Charley's Aunt (later adapted to film several times, and musicalized in 1948 as Where's Charley?) is a classic example.
  • In The Complete History Of America Abridged, three soldiers trapped behind enemy lines in World War I hatch a Zany Scheme to escape: dressing up not as Germans but as The Andrews Sisters, an anachronism justified by the Rule of Funny.
  • In A Funny Thing Happened on the Way to the Forum, Hysterium is talked into impersonating the "dead" courtesan Philia.
  • Head over Heels has Musidorus, who takes on the personage of an Amazon so he can reunite with his love interest.
  • The basic premise of Leading Ladies, a farce by Ken Ludwig (best known for Lend Me a Tenor). Two down-on-their-luck Shakespearean actors find out they have an opportunity to receive the legacy of a wealthy old woman ... but only if they can successfully pass themselves off as her long-lost nieces.
  • The page Cherubino is disguised as the Countess's maid to avoid the Count's vengeance in The Marriage of Figaro. In both this and the Der Rosenkavalier case above, the character is already being played by a woman.
  • Shakespeare has a lot of Sweet Polly Oliver characters, but the only time he uses the reverse situation is in The Merry Wives of Windsor, in which Falstaff disguises himself as the extremely fat Witch of Brainford in order to get out of the Fords' house after Master Ford comes home early. Hilarity, naturally, ensues.
  • In Peter Pan (1954), after the rescue of Tiger Lily, Peter leads Captain Hook on a comic, musical chase disguised as a beautiful veiled lady, in the duet "Oh My Mysterious Lady." This scene has no basis in the original play or book, was chiefly added to showcase Mary Martin's operatic voice, and has been cut from several later productions such as those starring Cathy Rigby.
  • Princess Ida, and the narrative poem by Tennyson it was based on, has the protagonists donning women's clothing to infiltrate a women's college.
  • In Richard Strauss' opera Der Rosenkavalier, the 16-year-old boy Octavian is made to dress as a chambermaid for a Honey Trap scheme against Baron Ochs.
  • Some Like It Hot: Musicians Jerry and Joe need to flee Chicago because they've witnessed a murder. They pass themselves off as women and join an all-female band. The number "Vamp!" is all about how the identities will keep them alive. Jerry eventually realizes that he enjoys not just drag, but being a woman, and embraces Daphne as her new identity.

    Video Games 
  • In The Feeble Files, when Feeble becomes the number one most wanted criminal, he puts on a dress and a wig to walk around the Metro Prime unopposed. Everyone completely falls for it.
  • In Final Fantasy VII, Cloud dresses up as a woman to infiltrate a harem. Depending on your choices in finding components for his disguise, he may be deemed more attractive than the two actual female party members with him. It's also worth noting that, even without the best and sexiest components for his disguise, he's still deemed attractive enough for all of the Don's lackeys to want to bang him. The remake has him get picked regardless of how well he gets his dress, and he doesn't even bother to change his voice at all.
  • In the first game of the Galaxy Angel II trilogy, Kazuya is forced to crossdress as a maid named "Katherine" if players choose to pursue Natsume Izayoi in the later installments. This is the only on-screen appearance of this trope in regards to Kazuya, who was often forced to crossdress previously at a cafe he worked at before joining the Rune Angels. He's lucky Lily knows a technique that quickly negates a curse from a fruit he consumed on Sprite during the events of the trilogy's third game, which she deploys almost immediately (again in Natsume's route, whereas it takes an Emblem Frame malfunction for Lily to use this on Anise in the redhead's own route as there it's Anise who consumed the fruit in question and not Kazuya).
  • Genshin Impact's Sumeru story arc has Isak, a young boy from the Aaru Village, volunteering himself to crossdress as the Dendro Archon Nahida to fool the Akademiya guards when the Traveler and their Sumeru accomplices hatched a plan to rescue Nahida from her prison at the Sanctuary of Surasthana.
  • In a drama CD Yuuya of Hatoful Boyfriend puts on a maid outfit for a stakeout. He's a bird and of a species where males and females look alike - it's specifically noted that dresses are a common element in jobs high school boys take - and it probably would have gone unnoticed if two schoolmates hadn't recognized him.
  • The actual gender of Jazzpunk's protagonist Polyblank is not elaborated on in-game, but the live-action teaser trailer features a man. In the third mission, you have to disguise yourself with a wig and lipstick in order to cozy up to an enemy agent and then covertly switch out his briefcase with a dummy. The agent seems quite taken with disguised-you, but it turns out to be an act; he's onto you and has you drugged and dumped in an unoccupied hotel room, sans briefcase.
  • Alexander will dress up in Beauty's clothes for re-entry into the castle if you chose the short path in King's Quest VI: Heir Today, Gone Tomorrow.
  • The Legend of Tian-ding has the Jiangyue-lou Restaurant stage, where your titular character disguises himself as a waitress to investigate one of the Les Collaborateurs. You then pulled a Contrived Clumsiness spilling wine on him, before offering to clean his shirt... and pickpocketing a vital Macguffin you need to complete the game.
  • The Legend of Zelda: Breath of the Wild has Gerudo Town, a town where only women are allowed to visit. To get inside, Link has to dress up in the same garb as the Gerudos. The person who sells him the clothes finds Link very adorable after the clothing change and it helps that Link is already a pretty boy by default.
  • In Monkey Island 2: LeChuck's Revenge, Guybrush has to wear a pink lady's dress as a costume in order to sneak into Elaine's Booty Island mansion.
  • The boss battle against the Girl-Eating Plant in Nicktoons: Globs of Doom invokes this: in order to damage it from the inside, SpongeBob and Technus have to find several clothing stores and put on dresses, which fools the plant into thinking they're girls and eating them.
  • Captain Qwark, the so-called "superhero" in the Ratchet & Clank series, has a tendency to sneak into places by being disguised... in drag. This is most notable in Up Your Arsenal, and A Crack in Time, where he snuck around Nefarious' Space Station as a Pizza Delivery Woman and "Nurse Shannon", respectively. While his broad shoulders, huge chin, and overall masculine appearance make his disguises very paper thin, he's managed to fool a select few people (namely a taxi driver and Clank of all people.)
    Nefarious: The famous Captain Qwark couldn't possibly be this stupid... could he?
  • Red Dead Redemption 2: The provocative French artist Charles Châtenay goes undercover in incredibly unconvincing drag — the chest hair and beard are a bit of a giveaway — to flee town when his paintings prove too avant-garde for the 19th-Century Wild West. Somehow, he still attracts a few men's interest... until they get closer.
  • Romancing SaGa: After his friend Farah is kidnapped, Jamil does this so that he can get into Wuhan's secret harem. Notably, he dons the dress before trudging through the sewers to North Estamir.
  • This is how Michael gains access to the Lady Land of Shecola in StarTropics.
  • One portion of Summon Night Swordscraft Story 2 involves you needing to get past a monster to progress, however he won't let someone without sex appeal go through. A character named Bryon ends up dressing as a woman to try and convince the monster to let him through.
  • Tales of Vesperia features a chance to do this. When the need arises to seduce your way past a guard, Yuri is given the choice of two of his female party members (Estelle or Judith) or forcing young boy Karol into a pretty pink dress and bow. Worth noting is that using "feminine wiles" on the guard was Karol's idea in the first place, making this perhaps a Karmic punishment. All three of the outfits become purchasable costumes later on in the game, meaning that you can have Karol be wearing his dress whenever you feel like it.
  • Tales of Graces has this when the party performs a play version of Snow White in Velanik. For some reason, the role of the Evil Queen doesn't go to Pascal or Sophie...but to Hubert. Of course he's completely unwilling and a rather stiff actor. The "disguise" part comes in when a man in the crowd recognizes Hubert as Strahta's top Lieutenant. In order to protect his identity, Hubert goes full-bore Large Ham, complete with squeaky feminine voice, and the spectator concludes that no respectable officer would be caught dead crossdressing on stage.
  • In one questline in the Storm Peaks of World of Warcraft, your character gets disguised as a vrykul warrior maiden. This is more than just a disguise, however; if your character is male and has earned the title "Patron", the title automatically changes to "Matron" in every zone where the disguise is in effect.
  • Super Mario Bros.:
    • Luigi has done this in the Mario RPGs twice. In Mario & Luigi: Superstar Saga, Luigi was dressed as Peach to get near Fawful and retrieve the Beanstar. He also has done this offscreen in Paper Mario: The Thousand-Year Door, where he had to dress as a beautiful maiden (though most of everyone else around him needed Brain Bleach).
    • Prior to this, a comic published in Nintendo Power had him switch clothes with Peach after the Koopalings caught Mario and threatened to kill him unless the just-escaped princess was returned. (Peach proceeded to wear his overalls for the rest of that arc as she led the others in Storming the Castle.)
  • Yakuza Kiwami has "Goromi-Chan" as part of the "Majima Everywhere" system, an encounter that sees Goro Majima in Incredibly Conspicuous Drag waiting for Kiryu to visit the particular hostess club he's set up shop in. Kiryu isn't fooled, but plays along and ends up having a decent conversation with his Friendly Enemy Majima... until Majima asks him out on a date and takes Kiryu's refusal as an excuse to get into a drag-out brawl in the street.
  • Grand Theft Auto: Vice City has a storyline where you must protect Love Fist from a Stalker without a Crush. He hides among an angry crowd of their fans, wearing a very conspicuous woman disguise that contrasts with the actual female NPCs there.

    Web Animation 
  • Louie and Dewey dress up as the Spice Girls in Ducktalez 6, as part of Darkwing's distraction.
  • Manga Room: Yuzusa is tasked by Manaka's father to monitor her behavior by transferring him into an all-girls school, which she currently attends. He also has to wear a female school uniform and a wig to maintain his cover. Due to his appearance, two other girls in the school are attracted to him, causing him to have an unwanted harem around him, including Manaka.

  • 8-Bit Theater: The "heroes" crashland an airship into an all-women elven barracks and quickly dress as women, introducing themselves as Thiefica, Fighterina, Black Magia, and-
    Red Mage: Debora.
    Red Mage: Don't look at me like that. I've always thought Debora was a pretty name.
    Black Mage: Let's just try to ignore Red Mage's transvestite urges and get the hell out of here.
    Red Mage: I am secure enough in my own sexual identity and orientation that I can ignore your base and inflammatory remarks, Black Mage. In fact, I won't even dignify your infantile statement with a response. Besides, I'm not the one who wears a long, flowing garment like some other Light Warriors I could mention.
    Black Mage These are robes!
  • Batman: Wayne Family Adventures: When spying on Duke's date Tim wears a version of his Caroline Hill disguise, which is passable, but Stephanie wears an overlarge jacket and conspicuous fake mustache while Damian doesn't bother with a disguise at all.
  • In Castlevania RPG, Alec has disguised himself several times. When he tries to infiltrate the Ranger's Guild castle with Jennifer and Cassandra Belmont, they're captured because the latter doesn't look female enough.
  • In Divine Bells, Hong-Ryeong dresses as a maid at one point to avoid detection while sneaking around his palace.
  • In Drowtales, Nau'kheol and Khal'harror are forced into this so they can sneak into the girls' section of the school. They're assisted by Sorane'sanil, who does this on a regular basis, and while Sorane gets caught because one of the teachers recognizes him, the other two manage to pass.
  • In Far to the North a group of Saengorian slavers cover themselves to avoid attracting the attention of the Goblin who guards the woods near the Rethuii, the native peoples of the North, since their dark hair makes them a target and the Goblin apparently won't attack women regardless of their ethnicity.
  • In The Order of the Stick, Roy gets turned into a woman by a girdle of masculinity/femininity, and must fend off the amorous advances of his fellow party member Belkar (who knows that it's really Roy and is doing it on purpose just to creep him out).
    • From comic 235, "The lesson here is, if the magic item doesn't specifically SAY it grows hair, it probably doesnt". He uses a mop head as an improvised wig.
  • Dillon, the title character of Sticky Dilly Buns, is a Camp Gay actor with a gift for cross-dressing (as was previously illustrated when he was a secondary character in Ménage à 3; some readers found him quite unnervingly attractive). He uses this for disguise at least once — but then, the Rule of Funny ensures that he meets at least a couple of people who know him well enough to see through the disguise instantly.
  • Unsounded: Lemuel has Miki disguise herself as a boy for her trip home using a glamor.
  • Your Throne: Lady Medea sometimes disguises as a man when sneaking around at night. She does a very convincing job at it, nearly completely altering her body-type (it helps that she is very muscular through her training).

    Web Videos 
  • Lee Phillips dresses as a woman in the KateModern episode "The Hen Night", in order to attend the hen night (and investigate the ladies' toilets).

    Western Animation 
  • In the Adventures in Care-A-Lot episode "Battle of the Band," Grizzle dons a Wig, Dress, Accent to pose as "Busybody Bear" and spread a little gossip to break up a recently formed band, whose practicing was keeping him from getting any sleep.
  • Taking a cue from Looney Tunes, Adventures of Sonic the Hedgehog has this happen a lot with Sonic. Sonic even uses his disguises to seduce Robotnik once in a while. The other characters get into it, too — Scratch does it twice (both times, to seduce Sonic) and Grounder has ended up in bridal garb twice (to Scratch's groom), and dressed as a little girl once.
  • The Amazing World of Gumball: In "The Lady", Richard is shown to have a female alter ego named Samantha, which he created in order to befriend a group of sassy older ladies after unsuccessfully trying to find some guy friends. At first, Gumball and Darwin believe that Richard is cheating on their mother with Samantha, but when they realize that Richard is Samantha, they immediately go to stop Richard from breaking off his friendship with the ladies. Turns out two of the other ladies are also men, and they all decide to maintain their friendship, disguises and all.
  • Around the World with Willy Fog includes a villainous example. Transfer's first two attempts to stop Fog and his party involve him dressing up as attractive females. Averted in later episodes as Transfer's other disguises are all male.
  • Avatar: The Last Airbender:
    • Sokka dons the uniform of a Kyoshi Warrior in an early episode. Suki manages to talk Sokka into feeling pretty good about it... until Aang strolls by and compliments him on his "nice dress". Made even funnier when you consider Aang's comment earlier in the episode:
      Aang: Where we're going, you won't need any pants!
    • Little did Aang know that he'd be stuck putting on the "nice dress" of the founder of the Kyoshi Warriors only a few scant months later. And then vamping in it.
    • Sokka, at least, never quite lives it down. From a speech explaining his history with the Avatar in front of the entire Black Sun invasion army:
      Sokka: And then we met Suki, who's a Kyoshi warrior. She made me dress like a woman, and then she kissed me[this is the point where his father steps in to shut him up, though it takes him a few (hilarious) seconds to reach the podium]
  • Classic Disney Shorts: Combined with Paper-Thin Disguise in Casey Bats Again. At one point, Casey disguises himself as a girl (rather badly at that) to try and help his daughters win a baseball game.
  • Chowder: "The Broken Part": After Chowder steals the last Feetza 5000 replacement set from the person who bought it, the guy takes off his costume and gives chase to Chowder. In order to lose him, Chowder finds a store called "Ladies B Us", and disguises himself as a women and points the guy who is chasing him in a different direction.
  • Chip 'n Dale: Rescue Rangers: "Adventures in Squirrelsitting": Chip and Dale not only dress up as girls but put on a show in order to sneak into Fat Cat's hideout.
  • Dexter's Laboratory: In "The Muffin King", as Dad's first attempt to sample Mom's dinner muffins unguarded, he disguises himself as Mom and tricks Dexter and Dee Dee into leaving the house. The kids are fooled at first, but then they see right through the disguise when Dexter points out that "Mom" is looking "stubbly" today.
  • Eek! The Cat: Eek does in the second episode "Bearz 'n the Hood", when he and the Squishy Bears steal laundry clothes from a very grouchy woman and dress as hula girls so they can catch a ride on a pickup truck.
  • The Fairly OddParents!
    • "Operation: Dinkleberg": Timmy is dragged into one of his Dad's plots in spying on Mr. Dinkleberg, and has to deliver a box of pastries with a camera in them dressed as a girl scout.
    • In another episode, when Francis is celebrating the last day of school by beating up all the boys, one nameless boy tries to hide by dressing up as a girl. It doesn't work.
  • Family Guy:
    • "Go, Stewie, Go!" has Stewie disguising himself as a girl in order to land a role on the American version of his favorite children's show, Jolly Farm (References to both Mrs. Doubtfire and Tootsie also appear in this episode) mainly because as he was waiting to get an audition, he was informed that all the male roles in the show were filled.
    • In another episode the family is forced to live in Texas thanks to the population of Quahog believing Stewie is possessed. Stewie ends up competing in a child beauty pageant.
  • The Flintstones: "In the Dough": Fred and Barney disguise themselves as women to enter a baking contest when Wilma and Betty get the measles.
  • Futurama: "Raging Bender": Bender is forced to wrestle as the Gender Bender, in a tutu and blonde wig. And in "Bend Her", he undergoes a robo-sex change to compete in the Olympics under the name Coilette.
  • G.I. Joe: A Real American Hero: The DiC Entertainment era had the trope occur in the episode "United We Stand", where Ambush and Pathfinder are ordered to stay in sickbay but are the only ones available to thwart Cobra's latest plot. To sneak out, they disguise themselves as female nurses.
  • Kaeloo: In Episode 60, Stumpy tries to gain access to a nightclub, but the bouncer refuses to let him in since it's only for girls. He comes back in a wig claiming to be a girl, and is granted access.
  • in French Animated series KangarooJuniors: In Episode 20, five young kangaroos diguise themselves in drags and act like little girls.
  • Looney Tunes:
    • It's easier to name every short where Bugs Bunny doesn't dress as a female to deceive Elmer Fudd, who becomes instantly smitten with the disguised Bugs.
    • Rabbit of Seville: Played particularly weirdly. The climactic battle between Elmer and Bugs degenerates into them alternating chasing each other with more and more deadly weapons...until Bugs abruptly comes up with a series of courting gifts (flowers, chocolates, and so forth, finishing with a diamond ring) and Elmer runs off and comes back in a wedding dress.
    • Corn On The Cop: A non-Bugs Bunny example occurs. Set on Halloween, a robber disguises himself as Granny after she had recently visited a grocery store for treats to give out to trick-or-treaters, and he would rob the same store after the fact, prompting a pursuit by incompetent policemen Porky and Daffy as they try to arrest either of the two. Granny becomes aggravated with what's going on, thinking the robber and the two cops were kids in costumes.
    • "Daffy's Southern Exposure": A wolf and weasel who are sick of having nothing to eat but canned beans try and capture Daffy and fatten him up for dinner while disguised as harmless old ladies.
    • The Looney Tunes Show: Invoked again in an episode where Bugs disguises himself as "Viola Bunny" his "sister" moving to Albania, all as a ploy to avoid going to a peach festival with Porky. Later subverted when he's detained at the Albanian airport for not having a matching passport.
  • The Loud House:
    • "Cover Girls": Lincoln not only has to spend a good part of the episode dressed as his infant sister Lily while eldest sister Lori is forced to wear his clothes (for reasons), but Lincoln turns out to have copies of all of his sisters' standard attire just in case he needs to dress as one of them.
    • "Novel Idea": At the beginning, Lincoln does this in an attempt to attend Take Your Daughter To Work Day with his dad.
  • Mickey Mouse (2013): "Shifting Gears": Mickey's living car is uncooperative in letting Mickey take it to the beach, so one of his plans is to get in it disguised as Minnie. When the real Minnie appears, Mickey's disguises quickly fall apart and he instantly grows a 5 o'clock shadow.
  • Mickey Mouse Works: "Mickey's Big Break" is about Mickey and Donald accidentally breaking a picture of Minnie and Daisy while playing football inside, so they had to go out and crossdress as their own girlfriends to replace the photo and get Goofy to take a picture of them once they get back so Minnie and Daisy don't find out. At the end of the short, Minnie and Daisy do find out, and reveal they've always hated that photo and replace it with a One-Millionth Customer photo they got at the department store.
  • My Little Pony: Friendship Is Magic:
    • "Rarity Investigates!": Wind Rider disguises himself as a mare in an attempt to frame Rainbow Dash for a crime.
    • "Brotherhooves Social": Big Macintosh disguises himself as a mare so that he can compete in the Sisterhooves Social events with his little sister. His disguise fools exactly one person. He ends up getting disqualified, not because of the drag (the judges knew it was him and didn't care), but because of his unsportsmanlike conduct during the race.
  • The New Archies: After Reggie pranks Fang, he has to convince Veronica to ask Fang to a dance. Veronica refuses, so Reggie dresses up as Veronica and goes to the dance with Fang.
  • The Perils of Penelope Pitstop: No fewer than three episodes have the Hooded Claw do this. In "Cross Country Double Cross", he dresses as an old woman to hitch a ride on Penelope's motorcycle, and, in two other episodes, he impersonates Penelope herself.
  • Pinky and the Brain: The duo are always wearing disguises, and about a third of those involve women's clothes.
  • Popeye:
    • "Vim, Vigor, and Vitaliky": Bluto, to show up Popeye at his ladies-only gym, disguises himself as a woman — an ugly, ugly woman.
    • "Too Weak to Work": Popeye and Bluto are both Navy men — Bluto feigns illness to get out of work and asks a sympathetic Popeye for "a pretty nurse"... Popeye then sees he's perfectly fine and disguises himself as a nurse. Bluto is horrified.
  • The Powerpuff Girls (1998):
    • "Powerpuff Bluff": A trio of hulking convicts come up with the idea of dressing up like the girls to go on a crime spree unhindered — and it works! They look through their prison cell wondering how they can pull it off — the camera pans from bunks chained to the wall, a toilet, a locker with three Powerpuff Girl costumes...
    • "Slumbering with the Enemy": Mojo Jojo disguises himself as a girl named Mojesha as part of his plan to destroy the girls at a Slumber Party they host.
    • "Film Flam": A director comes to town wanting to make a movie about the Powerpuff Girls. Professor Utonium realizes something is up and goes to foil his plans, dressing in drag in order to do so. At the end of the episode, the Narrator laments how the Professor in drag looks just like his mom.
  • The Problem Solverz: In episode "K-999 and Da Little Explorerz", Alfe dresses as a girl scout so he can get Nina's missing semaphore badge for her. He changes his name to Alfena, dons glittery makeup, and somehow manages to fool everyone, even though the scouts have a radar that can detect boys in their organization.
  • Recess: Gus does this in the final episode as part of T.J.'s plan to get their baseball bat from the Ashleys.
  • Robotomy: "The Trials of Robocles": While making his Run for the Border, Mr. Dreadnot dressed himself in women's clothes as part of trying to change his identity. Notably, robots do not otherwise wear clothing of any sort.
  • Rugrats: In one episode, Stu and Lou Pickles dressed Tommy up in a dress and a wig to enter him into a baby beauty contest to win a fishing boat. Didi was not happy.
  • Sally Bollywood: Doowee has had to disguise himself as a girl on a few occasions. In "The Egg War" he ends up dressed up in one of Sally's saris (complete with a wig and makeup) in order to download a message off a girl's phone, and in another episode, he ends up dressed as Little Red Riding Hood, in order to get onstage.
  • Samurai Jack: In "Jack is Naked", Jack, while looking for his stolen clothes and being chased by an angry mob, is dragged onto a play and dressed as "the Princess of Hearts", who just happened to resemble Alice.
  • Scooby-Doo examples:
    • Shaggy and Scooby are forced to dress as women in the first episode of Scooby-Doo! Mystery Incorporated so the team can search a suspicious location that was hiring female workers. This is despite both Daphne and Velma being on hand to do so themselves, which Shaggy questions. Daphne gives them a simple answer: She and Velma refused to do it.
    • In two of the Scooby-Doo DVD animated movies, Shaggy is dressed as Daphne and Scooby is dressed as Velma.
    • The plot of Scooby-Doo in Arabian Nights centers around Shaggy disguising himself as a harem and then having the Caliph wanting to marry him. Shaggy has to pull a Scheherezade Gambit to get out of the wedding.
  • The entire premise of SheZow has the male protagonist inheriting his aunt's secret identity, a superheroine. It's convincing enough to fool his own dad, a cop who has a long-standing beef with SheZow.
  • In The Simpsons, Abe Simpson told a story about how he got stranded behind enemy lines and rode out the war dressed as a German cabaret singer. In the flashback, he has the perma-stubble.
  • The Smurfs
    • Hefty Smurf of The Smurfs (1981) had to disguise himself as Smurfette to protect her from the unwanted affections of a troll king.
    • Hefty and Scaredy in The Smurfs (2021) episode "Smurfs In Disguise" disguise themselves as female Smurfs when they accidentally break Papa Smurf's telescope.
  • South Park examples:
    • Mercilessly parodied in "Butter's Bottom Bitch". The police chief dresses as a female whore as part of a sting operation. At least half a dozen guys fall for this, but the police chief takes the operation a step further and actually HAS SEX with the men looking to solicit prostitution. The police chief takes it ANOTHER step further and actually gets married. To his pimp.
    • Played more or less straight in "Marjorine". The boys discover the girls with a cooty-catcher and believe it to be a future-telling device. In order to steal it, they force Butters to fake his own suicide, dress up as a girl and infiltrate the girls' slumber party.
  • SpongeBob SquarePants:
    • In an episode, Patrick wrongly thinks someone is threatening him, so he crossdresses so he can stay. Hilarity Ensues when every male character besides Spongebob (who's in on the whole thing) to go positively ga-ga over him. From Mr. Krabs to Squidward, and Larry the Lobster.
    • In "The Cent of Money", Mr. Krabs tries to exploit Gary's apparent ability to attract money by going to the arcade dressed as a woman, with Gary hidden under the dress to make him look pregnant.
    • Brilliantly subverted in "The Slumber Party". Pearl is having a slumber party with her girlfriends, and Mr. Krabs is worried about the damage they might do to his house, so he tells Spongebob they have to find a way into the party. Cut to what is obviously Spongebob in a dress, wig, and lipstick, going up to the front door and introducing herself as "Girly Teengirl from Farawayville" while making no effort whatsoever to disguise his voice. Pearl and the other girls don't buy it, and "Girly Teengirl" runs off crying right as Spongebob and Mr. Krabs drive up to the house in a pizza delivery truck and watch her run off in confusion.
      Mr. Krabs: Who the heck is that?
      SpongeBob: I dunno, but she is ug-leeeeee.
  • Star vs. the Forces of Evil: In "St. Olga's Reform School for Wayward Princesses", Star makes Marco dress as a princess in order to help her infiltrate a Boarding School of Horrors. Marco is reluctant at first but gradually gets into the role of "Princess Marco", to the point where "she" becomes a figurehead of the student rebellion when they overthrow the cruel headmistress, Miss Heinous. Later in the series, “Princess Marco” becomes something of a celebrity in the other dimensions, even having “her” own toy-line of dolls.
  • A stock disguise and diversion in the TaleSpin universe, to the point it might overlap with Wholesome Crossdresser:
    • In the episode "Feminine Air", Baloo dresses as a woman because he wants to take part in a flying competition, but the last sponsor taking any applicants only accepts women. He also gets paired with his female boss as a navigator and has to fool her throughout the episode. Which he doesn't; at the end, he learns that she recognized him all along.
    • In "A Spy in the Ointment", Baloo has to dress up as part of a gypsy performance troupe (and only complains about having to wear uncomfortable boots as opposed to anything else).
    • At one point during "For Whom the Bell Klangs", Louie dresses up as a belly dancer as a distraction.
    • In "Flying Dupes", Baloo disguises himself and Sgt. Dunder as showgirls after forwarding the clock at Ivan's bar to 3:00, as he is tasked with delivering a package to the Thembrian High Marshall by 3:00 (unaware that the package contains a bomb), and Col. Spigot refuses to leave Ivan's until after 3:00 when the showgirls perform.
  • Toxic Crusaders has at least one occasion where Psycho and Bone-Head would be disguised as part of their boss's schemes. This led to the lovely sight of the Fat Bastard Psycho in a dress.
  • In the very first episode of What's with Andy?, Andy tries to annoy his sister Jen by mimicking everything she does. This becomes a problem for him when Jen decides to go to the school dance in a dress.
  • Woody Woodpecker pulls this a couple of times to yank Buzz Buzzard's chain. In "Drooler's Delight," Woody goes in drag to woo Buzz who stole his quarter, and in "Real Gone Woody," he's a drive-in restaurant carhop giving Buzz (who stole Woody's girlfriend Winnie) an explosive banana split.

    Real Life 
  • During the 1973 Operation Spring of Youth, in which Israeli special forces attacked key members of terror organisations residing in Lebanon, unit-commander (and future PM of Israel) Ehud Barak was disguised as a brunette woman.
  • In the time of Julius Caesar, Roman politician Clodius disguised himself as a woman in order to infiltrate the Women's Mysteries. He got away with it until forced to speak. The punishment would have been severe if he hadn't somehow weaseled his way out of it. Afterward he was very angry at the high priestess, a Vestal Virgin and years afterward took revenge on her. (Vestal Virgins could and did abandon their positions. Said priestess got married... but Clodius arranged for her to have a very unsuitable match.)
  • In the first season of Australian Idol, Shane Jenek didn't make it past the auditions (among other things, his voice is unusually high for a man). Since he just so happens to also perform as a Drag Queen and one who can pass as a natural woman, he came back the next day as his drag persona "Courtney Act" and made the cut. He was spotted by only one of the judges, but they decided he was good enough to keep in. 'Courtney' made Final 3, then made the cut at the 'Wild Card' part, and made the finals. In fact, 'she' was one of only three people from that season who got a record deal, and 'she' made it to number 29 in the ARIA charts with the song "Rub Me Wrong". Based on that, FHM magazine picked 'her' as one of the top 100 sexiest women that year. Shane Jenek is still a guy.
    • For what it's worth, Jenek is one of the few Australian Idol alumni to gain worldwide fame, thanks entirely to his drag persona. He eventually relocated to the United States and, in addition to becoming a successful Youtube personality as Courtney Act, went on to compete in the sixth season of RuPaul's Drag Race and placed in the Top 3. He even won the UK's celebrity version of Big Brother.
  • In Afghanistan, smugglers will often wear burqas to hide what they're smuggling.
  • At the beginning of The American Civil War, May 1861, when secessionist troops were gathering at Camp Jackson in Missouri, it is said that the Unionist commander of troops in the area, Nathaniel Lyon, decided to scout the camp riding in a carriage disguised as Frank Blair's mother-in-law. Including a black mourning veil. To cover up his beard.
    • At the end of the war, there was a rumor in the Union that Confederate President Jefferson Davis was captured wearing women's clothing. This was echoed in numerous newspapers and political cartoons. However, most historians agree that this rumor was false.
    • There was a similar rumor about Abraham Lincoln after he was elected having to sneak into Washington DC by train disguised as a woman. While they did indeed have to sneak him in, fearing that he might be assassinated, the crossdressing part was false and probably wouldn't have worked too well since a 6'4" woman would have attracted quite a bit of attention.
  • After the Battle of Culloden in 1746, Bonnie Prince Charlie escaped Scotland by disguising himself as a washerwoman.
  • During the Philippine Revolution against Spain in 1896, Katipunan leader Andres Bonifacio once disguised himself by dressing as a woman to sneak past a Guardia Civil (Spanish-colonial paramilitary police force) checkpoint.
  • According to an urban legend in China, the much-esteemed founder of Communist China, Chairman Mao Zedong, once did this in his younger days to evade capture by the very anti-Communist regime in China at the time. With the reverencenote  the general Chinese public views Mao with, don't expect many to be willing to discuss this rumor, much less confirm it, though.
  • Inverted with Princess Diana- she once partied at a gay bar with Freddie Mercury after he dressed her up as a man to avoid being recognized.
  • In December 2020, the mastermind behind the long-running “Hollywood Con Queen” scam was arrested in the UK. The alleged scammer is an Indonesian man named Hargobind Tahilramani. Since about 2013, he’d been disguising his voice to that of various women executives, mostly in the entertainment industry, from all over the world. His impersonations ranged from Americans like Wendi Murdoch & Kathleen Kennedy to Singaporean hotel magnate Christina song, to fictitious Chinese movie executives to lure freelancers to Indonesia for fake projects. He’d have someone be the victims’ escorts and pocket the cash from their expenses.
  • According to legend, Alexander Kerensky, the leader of the ill-fated Russian provisional government, was forced to flee from the Bolsheviks during the Red October disguised as either a (female) Red Cross nurse or as a chambermaid. Regardless of whether there was some truth to the rumour, Communist propagandists had a field day with it.
  • A common myth is that men dressed themselves as women to escape the sinking of the Titanic. Men like William Sloper, Dickinson Bishop, Bruce Ismay, and William Carter were famously accused of doing this, though these accusations were false regarding these men. One man from Third Class did in fact use a shawl to hide under, but only did so after he had jumped in. A lady pitied the man and gave him her shawl as a disguise when an officer threatened to shoot the men hiding in the boat.
  • Sexual mimicry in animals occurs in many species, including some lizards, fish, and cuttlefish, often as a way for weaker males to sneak past stronger, territorial males who would chase them away from females. In some wasps, males may even mimic a female to induce a rival male to mate with him rather than the female the first male mated with.

Alternative Title(s): Disguised As A Woman


Constantine as Deb Turnbull

In an unconventional take on this trope, Constantine gets placed in a large device resembling a meat grinder and is squeezed into a rubber suit to look like Deb Turnbull so he can steal Robotboy from Tommy while the real Deb is out of the house.

How well does it match the trope?

5 (1 votes)

Example of:

Main / DisguisedInDrag

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