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Harmless Lady Disguise
Inara: So… explain to me again why Zoe wasn't in the dress?
Mal: Tactics, woman. Needed her in the back. Besides, them soft cotton dresses feel kinda nice. There's a whole… airflow.
Inara: And you'd know that because…?
Mal: You can't open the book of my life and jump in the middle.
Firefly

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).

Subtrope of Disguised in Drag. May overlap with Wig, Dress, Accent.

Examples

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    Anime and Manga 

    Comic Books 
  • Madam Fatal, a 1940s superhero, had this as his shtick, earning him a spot on Cracked's 7 Crappiest Superheroes.
  • Batman did it in Batman: 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.
  • Obscure villain He-She has the left side of a pretty woman, and the right of a tough man. His/her entire strategy for dealing with heroes is to turn so that only the female side is visible, thus making people think that he/she is weak like a woman and either harmless or needs protecting. Yeah.

    Film 
  • 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 The 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 existence of this trope in the popular imagination winds up getting the protagonist of Breakfast on Pluto (a possibly transgender Wholesome Crossdresser) in a lot of trouble. Kitten is not a violent person at all, but when a nightclub she visits is bombed, the authorities suspect that the biologically-male Irish person in women's clothing is an IRA operative, and she's arrested and treated very badly.
  • In the Jim Belushi comedy Taking Care of Business, Jimmy Dorsey disguises himself as his own mother to break into a prison. It somehow works.

    Folk Heroes 
  • 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.

    Literature 
  • 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. The noble lady employing the 'maid' is less than horrified to discover she's been dressed and undressed for the better part of a month by a young man. In fact she seems rather pleased.
  • 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 Fred Vargas' The Chalk-Circle Man, Augustin-Louis Le Nermord spends half his time dressing as an especially ugly old woman, which is part of his creepily elaborate plan to kill his wife.
  • In the world of A Brother's Price women are the dominant sex and men are so rare it's unthinkably dangerous for one to go out alone. Men are also long-haired, makeup-wearing, and don less practical prettier clothing. However, whores in this world do themselves up to look like men and take on male mannerisms - so when Jerin has to go out, he masquerades as a whore.

    Live Action TV 
  • In Doctor Who, the Second and Third Doctor have used these types of disguises. In Three's case, Captain Yates of UNIT compliments his handbag, and the Doctor threatens to slosh him with it (it's a bucket).
  • Quark in the Star Trek: 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!.
  • The title character on Baretta frequently did this. A couple of them can be seen in the opening credits.
  • 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.
    • In another episode, he's dressed as a bag lady as part of a movie he's working on.
      • In yet another episode, he pretended to be an old lady. More specifically, Murdock's mother.
  • 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.
  • In an episode of Grounded For Life, Sean is unable to change a flat tire, so he wears a shawl and pretends to be an old woman while Claudia shows some leg to flag down another motorist to help.

    Video Games 

    Webcomics 
  • The 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.

    Western Animation 
  • 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.

    Mythology 
  • 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.

    Real Life 
  • 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 1950s; he was caught because someone noticed that he was wearing men's shoes.
  • William Wallace disguised himself as a woman more than once.
  • Unfortunately a real tactic among suicide bombers, especially in countries where women wear concealing clothing, which makes disguising IEDs on their person much easier.
  • Ehud Barak dressed in drag and pretended to be another soldier’s girlfriend during Operation Springtime of Youth. The popular Israeli satire show Eretz Nehederet portrayed him once as going Ax-Crazy and demanding his dress to go fight at the slightest hint of an imminent armed conflict.

Gender Neutral WritingGender Blending TropesHermaphrodite
God GuiseDisguise TropesHiding in a Hijab
Guys are SlobsGender and Sexuality TropesHas Two Mommies

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