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See that harmless little lady over there? She's actually a man -- a masculine, adventurous man who uses the dress to appear harmless and hide in plain sight.
Men are active, women are passive. That's the way things are, at least according to traditional gender roles.
Thus, if a man wants to become invisible and appear nonthreatening, it can be beneficial for him to pretend to be a woman. In sharp contrast to most forms of regular cross-dressing, this is done as a way of avoiding attention.
Contrast Sweet Polly Oliver, which is something of the inverse of this trope, since those women dress as men in order to openly embrace the male gender role of being active and potentially dangerous.
Many of the examples specifically have a male character disguising himself as an old woman, which is somewhat less reliant on sexist perceptions since senior citizens are (stereo)typically weak and frail (and it's also somewhat more believable that a man could look like an older woman than a younger one).
Anime and Manga
- Joseph Joestar of Jojo's Bizarre Adventure disguises himself as a lady in order to get inside a Nazi compound. It doesn't work.
- In Fullmetal Alchemist, Roy runs into a kind old lady at a cemetery--who, it turns out, is actually Lt. General Graham.
- In the Moonlight Sonata arc in Detective Conan, after a young boy named Seiji Asou escaped the strange death of the rest of his family because he was hospitalized in Tokyo, he was adopted by an old friend of his dead family (which let him stay unnoticed), and grew up into a handsome (and girly-looking) doctor. He then returned to his island under the false name Narumi Asai (not totally false, actually)--as a female doctor--to investigate their murders and have his Revenge. He got away with almost all of it, confronting and then killing all the culprits while leaving strange music-related messages... but when he was caught by Conan, Seiji set his family's old house on fire and stayed inside as it burned down, calmly playing the Moonlight Sonata in his father's old piano despite Conan's desperate pleas for him to live. Note: he, like most villains in the series, was portrayed with so much sympathy that viewers would, at worst, consider him an Anti-Villain. Strangely, in Italy, due to homosexual connotations, the trope wasn't spelled out (but still implied) to get it past the Media Watchdogs.
- Madam Fatal, a 1940s superhero, had this as his shtick, earning him a spot on Cracked's 7 Crappiest Superheroes.
- Batman did it in The Dark Knight Returns, as an old female customer at a liquor store.
- A mob boss "disguised" himself as a woman for years to avoid being killed by the Punisher. His nephew later joined him out of fear of the same fate.
- Early Captain America disguised himself as a granny and Bucky as a small child and then going to Nazi-occupied France.
- Madmartigan's lady disguise ends up serving as this in Willow when the villains are searching the town he's in. It doesn't fool them for long, though...
- Agent Smecker in Boondock Saints dressed as a tartish woman to get through a mobster's defenses (and it's implied to get through their pants as well.)
- Eames, The Forger, does this in Inception to distract Fischer while Cobb brings him over to their side. Unlike most of these examples, he uses illusion rather than a physical disguise.
- Used by the villain of The Devil Doll to bluff his way through encounters with his intended victims and the police, and also as an excuse to carry around his "dolls" (actually miniaturized assassins) in public.
- The Swedish criminal Folk Hero Lasse Maja used this extensively. (Lasse is a traditional Swedish male name, and his real name. Maja is a traditional Swedish female name, and the nickname he used. It appears he was not a cross-dresser otherwise, he only used his female persona to carry out his schemes.)
- In one ballad, Robin Hood was nearly cornered when he exchanged clothes with an old woman. She was captured by the sheriff; he got away and brought his merry men to face down the sheriff.
- The Scarlet Pimpernel is famous for this, and probably the trope maker.
- In G.K. Chesterton's The Club of Queer Trades, a curate describes a gang of criminals dressed up as a group of respectable old ladies. Subverted, in that the "curate" himself is lying and in disguise.
- In Dorothy L. Sayers Lord Peter Wimsey story, "The Article in Question,” a lady's maid turns out to be a disguised male criminal.
- Starfighters of Adumar has the infamous "Escape Done In Drag". Wedge ordered his three pilots to get him four sets of women's clothing, in which they snuck into a base while a diversion went on. On Adumar, women can take all the combat positions men take, but Wedge and his pilots were male and being hunted by pretty much the entire city, so a group of four women would be less suspect.
- The Stainless Steel Rat once took several dozen army deserters through a military checkpoint dressed as women. On bicycles.
- In Harry Potter and The Goblet of Fire, Barty Crouch Jr. escapes Azkaban disguised as his elderly mother.
- In Monstrous Regiment, the soldiers attempt to gain access to a heavily guarded fortress by disguising themselves as washerwomen. Subverted in that all of the soldiers save the lieutenant are actually women...who just happen to be disguised as men. It Makes Sense in Context.
- In A Study in Scarlet Sherlock Holmes is fooled (for a while) by a man disguised as an old woman; he himself pulls off this disguise in order to trail a villain in The Mazarin Stone.
- In Michael Flynn's The January Dancer, near the end, Hugh at one point is disguised as a woman.
- In Doctor Who, the Second and Third Doctor have used these types of disguises, and in the case of Three, one of the members of UNIT hilariously lampshades it.
- Quark in the Deep Space Nine episode "Profit and Lace".
- Mal in Firefly pulled this stunt in one episode, pretending to be Jayne's wife.
Mal: I swear by my pretty floral bonnet I will end you.
- Used ad nauseam in Allo Allo.
- Newkirk occasionally utilizes a 'little old German lady' disguise to fool the Germans.
- The Lone Ranger disguised himself from time to time in order to reconnoiter; very occasionally he dressed up as an old woman.
- Hannibal once dressed as a nun on an episode of The A-Team.
- Neville Savage of Mission Top Secret once disguised as an old lady with his accomplice pushing "her" wheelchair. It allowed him to pass under the protagonists' nose, but they later find the discarded costume.
- A Mexican serial killer in Criminal Minds had an MO of dressing like a woman to (for reasons peculiar to his brand of crazy) prey on unsuspecting old women. Upon figuring this out, the specialists tell the local police... who, due to local outlooks and customs, drag in everyone who has history of cross-dressing. (Which may sound unfortunate-but-comical, but is actually completely Played for Drama; they say they're being made to look like idiots.)
- Captain Qwark disguises himself as a woman more than once in Ratchet and Clank Up Your Arsenal. One of the occasions was in a vidcomic sidescrolling minigame.
- Order of the Stick took this a bit further when Roy used a magical belt temporarily to turn female, in order to avoid some assassins, who, true to the trope, just assumed he was a prostitute and ignored him -- except for the dwarf, who invited him up to his room. That bit didn't end well for ANYONE involved. However, while their assumption falls under this trope, Roy just wanted to disguise himself and the belt was the only disguise on hand.
- At the end of Mulan, the villain has the place guarded to stop any soldiers coming in to save the day, but a few of Mulan's male colleagues talk their way in disguised as concubines.
- Ugly concubines.
- One of the villains on Dynomutt Dog Wonder assumed the disguise of an old woman so Dynomutt would help him escape in a taxicab. Blue Falcon wasn't so easily fooled.
- In Open Season 2 Elliot (who is a deer) dresses up as an old lady to get pass security to the pet camp where he thinks Weenie is being held prisoner. Somehow the man watching for trespassers completely falls for it, even mistaking another old lady (who was wearing the same attire as Elliot's disguise) for the culprit.
- Classical Mythology: Achilles' mother did this to him in an attempt to keep him from the war. Naturally, the plan fell apart when Odysseus presented all the girls he was hiding among with gifts and Achilles was the only one to immediately go for the sword.
- There are stories about Jesse James having done this.
- When Charles Stuart, the Young Pretender, was escaping from Scotland after the collapse of his rebellion, Flora MacDonald smuggled him onto a boat disguised as her maid.
- Male insurgents in the Middle East have been known to hide under burqas.
- As did a prime minister trying to escape during a coup in Iraq in the 50s; he was caught because someone notices that he was wearing men's shoes.
- William Wallace disgused himself as a woman more than once.