In a series of commercials for Bud Light a bunch of guys dress as women to take advantage of Ladies' Night at a bar, where Bud Light is for sale at a reduced price for women. To (almost) everyone it's obvious that they're really men.
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-.
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.
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.
A major plot element in the first half of ∀ Gundam, where the protagonist Loran is put into situations where he is forced to crossdress in order to become the Gundam's "alleged" pilot Laura. This is addressed directly in the last episode when one character asks Guin (the man who made everyone think Loran was a woman) why doesn't he just put him in a skirt himself.
Also happens to Tieria in 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.
Gundam ZZ had the male members of the Gundam Team crossdressing in order to infiltrate a enemy base (It Makes Sense in Context). Humorously, while Iino gets in easily, Judau gets turned away because he looks downright weird in a dress.
In 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.
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 first season of the Pokémon anime, 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 GagOnce a Season.
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.)
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 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.
Train from Black Cat 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.
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...)
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 school girl 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...
Although not normally used as a disguise, Hermione Ayasaki is once used as such in an alternate story, 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.
In Otome wa Boku ni Koishiteru, 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.
A plot point for episode 4 of Black Butler. And one guess who got dragged into the drag. Give up? Ciel.
And in season two we have Alois briefly disguising himself as a maid.
Conan EdogawaandKaitou Kid 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.
Conan once switched clothes with Ayumi to find some kidnappers (they wanted her to deliver the ransom.)
Played with much later: Kaitou knockes out and strips a girl named Sara to disguise himself as her, leaving her only in her undies... but Sara 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 a top without a bra at that moment.) Conan later explains everything, Kaitou is all "WTF?!" when told Sara's a girl... and cue to a very pissed off Sara in her undies drop-kicking him on the head.
Edward Elric himself from Fullmetal Alchemist has disguised himself as a girl only once in the first anime. Whether or not that was successful would be difficult to say.
There's one scene in episode 7 of Fractale where Clain Necran does this while roaming a city populated by Doppels.
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.
Lupin III 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.
Goemon, Jigen, and Fujiko 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.
In JoJo's Bizarre Adventure Part II, Joseph Joestar decides that the best way to infiltrate a secret Nazi in Mexico base is to don a Harmless Lady Disguise. Unfortunately, Joseph is a musclebound man standing nearly six and a half feet tall, and the Nazis didn't bring their Idiot Balls to work that day.
Joseph: Damn, those Nazis are impressive. How could they see through my female disguise?
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 was Dangerously Genre Savvy enough to see through it.
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 "Freya" 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 one Batman story, Tim Drake had to disguise himself as a female medical student to obtain samples from a hospital. Alfred explains that Tim was too young to pull off a male med student. Tim was not happy about it:
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.
Jimmy Olsen does it so often he keeps an extensive wardrobe of womens' 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!
Captain America and Paladin engage in one of the least convincing examples ever recorded when they have to pass unnoticed through Superia's base filled with female supervillains. They simply take the costumes (which, incidentally, are skintight) of two defeated villains and put them on, with no further attempt at disguise, trusting that the presence of a number of Brawn Hilda types among Superia's followers will be enough to deflect suspicion. It works!.* Captain America #387-392 (1991)
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.
In the backstory for SpeakingThroughWrittenWords'sHearth 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.
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.
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.
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.
The Dustin Hoffman comedy Tootsie. "Dorothy Michaels" becomes quite the man magnet, in fact. His/her own pursuit of a female costar is kind of complicated.
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.
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 in women's clothes on his way to school to avoid his tormentors. However already the 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.
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.
Lots of Carry On films. Usually with cleavage so low and chest hair so thick it verges on terrifying.
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 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.
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 infront of his wife.
In Tango and Cash, Cash (played byKurt 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...
In the original Total Recall (1990), Douglas Quaid tries to infiltrate Mars undetected by disguising himself with an animatronic "fat woman suit".
In Brain Donors, handyman Jacques dresses up as a ballerina during the big premiere.
In Hes My Girl T. K. Carter dresses in drag so he can accompany his best friend on a trip to Los Angeles. Really.
In Armed And Dangerous, John Candy's character and his best friend disguise themselves- John Candy's character dressess like Divine and his best friend (played by Eugene Levy) dressess like the cop from the Village People.
In Love Exposure, the protagonist Yu loses a bet and must cross dress 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.
Pee Wees 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.
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.
Thunderball opens with Colonel Bouvar, an adversary of Bond's, faking his death and dressing as his widow.
Pretty much the inspiration for Austin Powers spotting a club employee as one of Dr. Evil's mooks in drag.
In Like Flint - Flint's boss Kramden tries infiltrating a woman-run organization in a very unconvincing drag disguise.
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!"
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.
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 Terry Pratchett's Discworld novel 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.
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 uses 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 the 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.
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.
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 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.
In Malevil, there is Bčbelle. 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.
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.
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.
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."
In The World According to Garp, Garp dresses as a woman to attend his mother's funeral.
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.
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.
This trope does not, as a general rule, apply to Jamie Farr's character, Max Klinger, on M*A*S*H. Klinger merely crossdresses 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 After M*A*S*H. 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 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.
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 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.
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 "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."
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 the episode "Major Star" of Blackadder Goes Forth, 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.
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 played by Dave Foley, who had prior experience as a member of The Kids in the Hall 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.
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 isStar Trek, "extensive surgery" equates to waving a coloured bulb over the patient's stomach.
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.
Farscape. Played for drama and 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.
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 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.
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".
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.
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.
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
In Merlin, 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.
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.
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.
In one episode of The Sweeney a character played by Warren Mitchell (better known for Till Death Us Do Part) 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!"
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.
In Victorious, when Tori is terrified of doing a stunt, she makes Beck do it for her by dressing in her same outfit, which he does, oblivious to the rest of her friends.
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.
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.
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.
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....
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.
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 theif wanted to marry, and sat through a wedding feast before revealing his identity.
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.
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.
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!
Toward the end of the Vocaloid song "The Madness of Duke Venomania", KAITO 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.
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.
*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.
Myth And Legend
Norse Mythology: In the Poetic Edda ("Thrymskvida"), Thor disguises himself as the fertility goddess Freya 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 "Freya'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.
Prince Yamatotakeru, a semi-legendary figure in Japanese Mythology, was said to have dressed as a maidservant to kill members of a rival clan.
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.
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 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.
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.
Making things even better, 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.
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.)
Romancing SaGa: After his friendFarah 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.
Captain Qwark, the so-called "superhero" 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 "Nurse Shannon." While his broad shoulders, huge chin, and overall masculine appearance make his disguises verypaper thin, he's managed to fool a select few people. (Namely a taxi driver and Clank of all people.)
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.
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).
In Castlevania RPG, Alec has several times disguised. When he disguises to infiltrate the Ranger's Guild castle with Jennifer and Cassandra Belmont, they're captured because the latter doesn't look female enough.
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.
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.
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).
In The Gungan Council, C'orringath Ven'Traas and Ayin Kaes looked great as handmaidens for the queen of Naboo.
Louie and Dewey dress up as the Spice Girls in Ducktalez 6, as part of Darkwing's distraction.
In every Looney Tunes short where Bugs Bunny dresses as a female to deceive Elmer Fudd, Elmer becomes instantly besotted.
Played particularly weirdly in Rabbit of Seville: 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.
Used in the Chip 'n Dale Rescue Rangers episode "Adventures in Squirrelsitting". Chip 'n Dale not only dressed as a girls, but put on a show in order sneak into Fat Cat's hideout.
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 recgnized 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.
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.
In The Flintstones episode "In the Dough", Fred and Barney disguise themselves as women to enter a baking contest when Wilma and Betty get the measles.
In an episode of SpongeBob SquarePants 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 positively go ga-ga over him. From Mr. Krabbs to Squidward, and Larry the Lobster.
Bender does this on Futurama. In the episode "Raging Bender" he 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.
The Family Guy episode "Go, Stewie, Go!" has Stewie disguising himself as a girl on several occasions:
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 waitng 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 pagent.
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 "Majorine". 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.
Sokka dons the uniform of a Kyoshi Warrior in an early episode of Avatar: The Last Airbender . 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:
"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.
From a speech explaining his history with the Avatar in front of the entire Black Sun invasion army:
"And then we met Suki, who's a Kyoshi warrior. She made me dress like a woman, and then she kissed me—" (This was the point where his father stepped in to shut him up, though it took him a few (hilarious) seconds to reach the podium.)
In an episode of Rugrats, Tommy's Dad and grandfather dressed him up in a dress and a wig to enter him into a baby beauty contest to win a fishing boat. Tommy's mom was not happy.
Hefty Smurf of The Smurfs had to disguise himself as Smurfette to protect her from the unwanted affections of a troll king.
No fewer than three episodes of The Perils of Penelope Pitstop had the Hooded Claw do this. In "Cross Country Double Cross", he dressed as an old woman to hitch a ride on Penelope's motorcycle, and in two other episodes he impersonated Penelope herself.
In The Problem Solverz 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.
The titular character of Eek! The Cat did this once 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.
In an early Popeye cartoon, Bluto, to show up Popeye at his ladies-only gym, disguises himself as a woman - an ugly, ugly woman.
On The Powerpuff Girls, 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...
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.
Gus does this in the final episode of Recess as part of T.J.'s plan to get their baseball bat from the Ashleys.
Doowee from Sally Bollywood has had to disguise himself as a girl on a few occasions. In "The Egg War" he ended 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 ended up dressed as Little Red Riding Hood, in order to get onstage.
In the very first episode of Whats 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.
Timmy in The Fairly Oddparents episode "Operation: Dinkleberg" is dragged into one his Dad's plot in spying on Mr Dinkleberg, and has to deliver a box of pastries with a camera in them dressed as a girl scout.
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 Gaius 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 guy). He came back the next day dressed as a woman and made the cut as 'Courtney Act'. He was spotted by only one of the judges, but the judges 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.
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.
After the Battle of Culloden in 1746, Bonnie Prince Charlie escaped Scotland by disguising himself as a washerwoman.