History Main / DudeLooksLikeALady

* Huey Laforet from ''LightNovel/{{Baccano}}''. One character (Tick's younger brother) had to guess at his gender based on his voice -- and, even then, he wasn't really sure. Firo also skirts the trope a bit. Nobody's ever mistaken him for a woman, but cops and FBI members have a habit of taking jabs at his appearance, like insinuating that he only got promoted to Capo because he was pretty enough to sleep his way up the ranks.

* In ''LightNovel/ACertainMagicalIndex'', Last Order asked Accelerator if he was a boy or a girl because she couldn't tell.

* Totsuka Saika from ''LightNovel/MyTeenRomanticComedySNAFU''. The adorable tennis club member is noted to be cuter and more feminine than most actual girls by the protagonist narrator.

* Tamamo-no-Mae from ''VideoGame/{{Onmyoji}}'', who's so feminine despite being an adult man that he's even voiced by a woman. Later skins however tone this down until he's just a {{Bishonen}}, and then comes a skin for his SP form where even his voice actor is replaced by a male one, firmly averting this trope.

* ''LightNovel/FateApocrypha'' has Astolfo, Paladin of Charlemagne, who has long, pink hair in a braid, a penchant for rather androgynous clothing, a high-pitched voice, and the personality of a spunky teenage girl. He is also a guy. In-story, the only one who seemed to not realize this was Jeanne d'Arc, who freaked out a bit upon running into Astolfo coming out of the shower. Astolfo himself occasionally likes to mess with people by playing up his gender ambiguity, and is noted to not care particularly much about gender differences.

* ''WesternAnimation/TheSimpsons'': Homer doesn’t even remotely resemble a girl, yet in one episode he still gets mistaken for one. After he gets kicked out of Moe’s Tavern, he goes to a lesbian bar. After he complains about the bar’s lack of a fire exit, [[ScrewThisImOutOfHere he leaves.]] A nearby woman asks, “What’s her problem?”

* ''Webcomic/SequentialArt'': Art's neighbor, Roger Lapin, to the extent that he basically looks ''exactly'' like [[Film/WhoFramedRogerRabbit Jessica Rabbit]], right down to the ImpossibleHourglassFigure and... [[BuxomIsBetter generous bustline]]. Considering that Roger's very anatomy is female, as opposed to just having feminine facial features, it isn't clear whether he just looks like a woman or whether he actually is transgender. His wife, Jessica, is an inversion since she looks like a stereotypical overweight, bearded biker dude.

* In ''Roleplay/CosmicInterference'', it is downplayed, as Chara is not exactly a ''male'' per se, but Luna calls them by she/her pronouns and calls them a "little girl."

* Gren from ''Anime/CowboyBebop''. The second he speaks, it's obvious he's a man, but he looks very feminine and [[spoiler:due to an experimental and highly-addictive drug, he has boobs. Big ones]].

* ''LightNovel/IfHerFlagBreaks'': Due to his very feminine appearance and attire (thigh-high socks and shorts), Megumu is mistaken for a girl by many characters when they first meet him. The fact that he wears the male uniform (or, at least, the male blazer) is the only way anyone could see that he was actually a boy.

* Bridget from ''VideoGame/{{Disgaea 2|CursedMemories}}''. Just like every other human in the game, he was cursed with the appearance of a demon. Of course, in ''his'' case, the aforementioned demon form is that of a very feminine [[HornyDevils Nymph-like creature]]. {{Unsettling Gender Reveal}}s ensue.

-->-- ''LightNovel/BakaAndTestSummonTheBeasts''

* Hideyoshi Kinoshita from ''LightNovel/BakaAndTestSummonTheBeasts''. Hideyoshi looks like [[http://images6.fanpop.com/image/photos/39300000/Hideyoshi-Kinoshita-baka-to-test-to-shoukanjuu-39379167-400-400.png this]]. He has to keep reminding Akihisa (and everyone else) that he's actually a guy, and is at one point mistaken for his twin sister. This has gotten to the point that a) Hideyoshi being a third gender is a RunningGag, and b) Hideyoshi gets most of the {{Fanservice}} shots of the series... in what would be extremely potent ''female'' fanservice moments/poses, if not for Hideyoshi being, er, not female. StupidSexyFlanders ensues.

* ''LightNovel/{{Shimoneta}}'': Oboro not only [[AloofDarkhairedGirl looks]] [[http://ami.animecharactersdatabase.com/uploads/chars/11498-278228631.png the part]], but even ''[[CrossdressingVoices sounds like one]]'' without having to disguise himself, or his voice.

* A lot of guys from ''LightNovel/TheStoryOfSaiunkoku'', but especially Sa Sakujun, with his long pink hair. In the manga, Ko Kijin wins a men-in-drag contest basically by showing up.
* Yoshiki Nakameguro from ''LightNovel/StudentCouncilsDiscretion''. It's enough to instill some StupidSexyFlanders moments in Ken in episode 12.
* ''LightNovel/SwordArtOnline'', due to the random generation of the avatar, Kirito, who already looks [[{{Bishonen}} rather feminine]] ends up with this appearance while in GGO. As if he didn't have enough problems already (what with a guy running around doing ''real'' [=PKs=]), he now has to go around looking like Literature/SnowWhite! PlayedForLaughs as not only does every player in-game aside from Death Gun initially assume he's a girl, a rather cute one at that, he eventually starts playing into it for [[TheGadfly his own amusement]].

* ''LightNovel/ThatTimeIGotReincarnatedAsASlime'': Though he's technically [[NoBiologicalSex sexless]] despite identifying as male, Rimuru Tempest's [[ShapeshifterDefaultForm human form]] is repeatedly confused for a girl at first glance by strangers due to his natural beauty, with some even thinking he's a ''goddess''. {{Justified}} in that his human form is based off the female Shizue Izawa, who asked to be [[YouWillBeAssimilated absorbed by him]] in her dying moments.

* The viral "[[https://www.youtube.com/watch?v=R3V86de6m18 Thanks my name is Felix]]", in which [[spoiler:the cameraman compliments a cosplayer he assumes to be a girl, and is stunned to find it's a crossdressing male as equally crossdressing male character Felix Argyle from ''LightNovel/{{ReZero}}''.]]

* Rune of ''Manga/DragonKnights'' was used as a body double for a princess in the first volume. Later on he gets proposed to by a man who then pats down Rune's chest to confirm his claims of masculinity.

** Chrollo mistakes Kurapika for a woman when he first meets him. Then again, Kurapika WAS [[WholesomeCrossdresser dressed as a woman with a feminine hairstyle, and he did it very convincingly too]]. Chrollo seems more shocked at getting Kurapika's gender wrong than him being incapacitated and tied up in Kurapika's car.
** The youngest [[TheFamilyThatSlaysTogether Zoldyck]] son Kalluto has a very feminine haircut and always wears a black kimono. His fighting style involves a fan (an instrument commonly associated with feminity) he moves to [[PaperMaster manipulate paper cuts]].

** Even in ''Anime/InazumaElevenGo'': Kirino has feminine eyes and a rose pink hair tied into two pigtails. He is actually a boy, so don't be fooled be his appereance.

* Envy from ''Manga/FullMetalAlchemist'', who is male in the [[Anime/FullMetalAlchemist first anime series]] [[spoiler:being Hohenhemin and Dante's son]], but can shapeshift into a woman if he wishes. In the official character book for the manga, the section under Envy is described as "of uncertain gender". He even had a female voice actor in the original Japanese, English, and Hungarian dubs, and this appearance is played for laughs in the Chibi Party OVA.

** The youngest [[TheFamilyThatSlaysTogether Zoldyck]] son Kalluto has a very feminine haircut and always wears a black kimono. His fighting style involves a fan, an instrument commonly associated with feminity, he moves to manipulate [[PaperMaster paper cuts]].
** Even the eldest son Illumi, with his dark [[LongHairPrettyBoy long hair]], his big eyes and his thin silhouette, could easily pass as a crossdressing woman.

* In ''Manga/HunterXHunter'', Chrollo mistakes Kurapika for a woman when he first meets him. Then again, Kurapika WAS [[WholesomeCrossdresser dressed as a woman with a feminine hairstyle, and he did it very convincingly too]]. Chrollo seems more shocked at getting Kurapika's gender wrong than him being incapacitated and tied up in Kurapika's car.

** [[https://static.tvtropes.org/pmwiki/pub/images/asuramaru.png Asuramaru]]. A young, girly face, long hair, wearing long opera gloves and most importantly a slitted ''dress'' that reveals [[HesGotLegs most of the legs]], yet ''he'' is officially confirmed to be male due to him [[spoiler: being formerly Ashera Tepes, Krul Tepes' brother.]]

** Bruno Bucciarati, with his androgynous face and bob-style haircut , also qualifies and makes him look rather feminine, though he at least has a very masculine voice.

* Bridget from ''VideoGame/GuiltyGear'' is a {{subversion}}. In older games, Bridget was referred to as a boy forced to crossdress due to a superstition, with an appearance that [[UnsettlingGenderReveal fooled many characters]].[[labelnote:Fun fact]]On Website/ThisVeryWiki, Bridget used to be the TropeNamer for UnsettlingGenderReveal before the trope was renamed.[[/labelnote]] Bridget didn't even bother to correct most of the cast when referred to as a girl. However, in her ''VideoGame/GuiltyGearStrive'' arcade mode, Bridget starts to grapple with gender identity issues, and ultimately realizes that she's a UsefulNotes/{{transgender}} woman, one that identifies as such of her own volition rather than due to being forced to by others.

* Bridget from ''VideoGame/GuiltyGear'' is a {{subversion}}. In older games, Bridget was referred to as a boy forced to crossdress due to a superstition, with an appearance that [[UnsettlingGenderReveal fooled many characters]].[[labelnote:Fun fact]]On Wiki/ThisVeryWiki, Bridget used to be the TropeNamer for UnsettlingGenderReveal before the trope was renamed.[[/labelnote]] Bridget didn't even bother to correct most of the cast when referred to as a girl. However, in her ''VideoGame/GuiltyGearStrive'' arcade mode, Bridget starts to grapple with gender identity issues, and ultimately realizes that she's a UsefulNotes/{{transgender}} woman, one that identifies as such of her own volition rather than due to being forced to by others.

%%** The Silver Saint Lacerta Misty.

* Frequently done in Kaori Yuki manga, not just in terms of art, but as part of the storyline.
** ''Anime/SaintSeiyaTheLostCanvas'':
** Phantasos is a goddess who uses her power to try and trap El Cid in a dream world where can have the thing he most desires. This will leave her and the other Gods free to kill all of humanity. However, El Cid's only dream is to make his sword the sharpest blade in existence. Thus when he obtains said blade in the dream, he uses it on her immediately. Her beauty shatters revealing that she's a crazed middle-aged man who is absolutely furious with El Cid for ending the facade.
** Veronica is a long-haired, purple-lipstick clad and extremely feminine male. Oddly this doesn't seem to be a difficult fact for Tenma and company to recognize.

* Bridget from ''VideoGame/GuiltyGear'' is assumed by many characters to be a young girl, despite identifying as a boy at the time. In fact, Bridget doesn't bother to correct most of the cast. Ultimately, she comes out as UsefulNotes/{{Transgender}} in ''VideoGame/GuiltyGearStrive''.

* Bridget from ''VideoGame/GuiltyGear''. Many characters will assume he is a young girl, even though he knows he's a boy, and doesn't go out of his way to correct most of the cast.

* ''Film/TheHobbitTheBattleOfTheFiveArmies'': Dáin considers Thranduil to be so {{Elfeminate}} that he resembles a woman, and he calls the Elvenking a "pointy-eared princess."