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[[quoteright:350:[[Webcomic/DubiousCompany http://static.tvtropes.org/pmwiki/pub/images/DudeLooksLikeDubiousContent_680.png]]]]
[[caption-width-right:350:To be fair, this ''is'' more masculine than his prior [[GirlishPigtails hairstyle]].]]

->''"That lady has a really deep voice."''
-->-- '''[[WebAnimation/ZeroPunctuation Ben "Yahtzee" Croshaw]]''' during a crossover appearance on ''{{Unskippable}} - StarOceanTheLastHope''

Whether it is due to their gorgeous hair, delicate features, snazzy dressing, or fey nature, some boys get called "little lady" more often than they'd like. The opposite of LadyLooksLikeADude, this trope involves male characters who are frequently mistaken for female (by other characters).

'''Not to be confused with:'''
* WholesomeCrossdresser (when the dude ''wants'' to look like a girl)
* ViewerGenderConfusion (when ''you'' mistake a character's gender)
* {{Bishonen}} (male characters who are feminine or androgynous-looking -- some of those dudes do look like ladies, but what separates it from this trope is that it's normally not commented on by other characters)
* DisguisedInDrag (when the dude's dressing as a girl only for a specific reason)
* ManIFeelLikeAWoman (that's [[GenderBender a whole 'nother story]] entirely)
* {{Transsexual}} (when the "dude" identifies as a girl and is trying to pass as one)
* EverybodyWantsTheHermaphrodite (when the "dude" has female parts as well as male ones)

Frequently results in an UnsettlingGenderReveal; the difference is how much another character has invested in the dude actually being a lady (''Film/TheCryingGame'' versus any scene with Kazuki in ''GetBackers'').

Named for the Music/{{Aerosmith}} song, a RealLife example as it was allegedly [[TakeThat/{{Music}} written about]] MotleyCrue [[TakeThat/{{Music}} frontman Vince Neil]].

Compare AmbiguousGender and {{Bifauxnen}}.

----
!!Administrivia/InUniverseExamplesOnly

[[foldercontrol]]

[[folder:Anime & Manga]]
* Zaji of ''TegamiBachi'' has garnered more than few double-takes for his androgynous appearance.
* Huo Long from ''Manga/HaouAiren''.
* Kogure, from ''{{The Secret Devil-chan}}''.
* Alto Saotome from ''MacrossFrontier''. Well, it generally happened offscreen, but his [[{{Bishonen}} fine features]] and long hair make such reports rather believable. The fact that he's a trained (and talented!) Kabuki actor, who frequently played female roles ''and'' [[StrongFamilyResemblance is a dead-ringer]] for his gorgeous MissingMom, doesn't help either. Frequently addressed as "Princess", at one point he is even offered female clothing by a salesman who mistakes him for a girl.
** The first time he meets Ranka, she mistakes him for a beautiful woman. And even later ''describes'' him to Ozma with that in mind.
--> '''Ranka''': He was really pretty, like a [[EverythingIsBetterWithPrincesses princess]].
* Lord Geppelnitch ([[spoiler:or, rather, the human body he's possessing]]) from ''Anime/{{Macross 7}}'' looks and sounds so ridiculously feminine that nobody among the fans could believe he was a man. Near the end of the series he is seen shirtless, which finally proves it.
* ''SamuraiDeeperKyo'' has Yukimura, a handsome bishonen who is sufficiently androgynous that he can easily pass for a woman in the right clothes, and has a FEMALE ninja as his body double. Not a macho-looking female ninja either.
* Haku, of ''Manga/{{Naruto}}'' looks feminine to the point that the main character is left in shock when he learns [[UnsettlingGenderReveal that Haku is actually a boy.]]
-->'''Naruto:''' No way?! He's prettier than Sakura!
** If it weren't for the fact that names ending in -maru indicate that they're male, Gaara's uncle Yashamaru would have most people fooled as well. In some language version of the manga (not to mention the unofficial english databook.), the producers mistake him for a woman.
** Filler villain Benten in the ''Shippuuden'' anime. This is to the point where Chūshin quips that whenever Benten opens his mouth, it looks and sounds strange due to his masculine voice and feminine appearance.
** Upon seeing Sasuke as a baby Kushina thought he was a girl. He also looks similar to his mom. Itachi even more so. He looks just like his mom and has really long eyelashes.
* Hotohori of ''FushigiYuugi'' is initially mistaken for a woman.
** Likewise Nuriko, though [[WholesomeCrossdresser the dress]] probably guided most assumptions. Even when Nuriko stops wearing dresses and wears more masculine clothing, this trope becomes more apparent for him, especially when he still wears his hair in a long braid.
* Rentaro Taki from ''Battle Club'' takes this UpToEleven, to the point that he literally looks like a woman, complete with relatively large breasts and an attractive feminine figure. Even WordOfGod [[spoiler: state that it's a dude]] in spite of his appearance. The only thing that makes him a male is that [[spoiler: he has male genitalia]].
* Yu Kanda from ''DGrayMan'' was mistaken for a girl by Lenalee the first time they met as children. Even now, main character Allen has been known to use 'girly face' as an insult for Kanda. In chapter 210 there's a scene where a random guy in a bar hits on Kanda thinking he's a girl.
* Rune of ''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.
* Several characters in ''FruitsBasket'', mostly Ayame. The [[RapunzelHair long white hair]] ''doesn't help''.
** This ambiguity of this trope got played around with. Kakeru started calling Yuki, who gets told he looks like a girl rather often, 'ranger pink'. He's androgynous enough that Kakeru tricked his girlfriend into believing he really was a girl who was crossdressing as a boy in a CrowningMomentOfFunny.
* Shingo in the King of Brutes storyline in ViolenceJack. And, because this is Violence Jack, he is molested because of this. MANY. TIMES.
* When Kazuki of the Strings in ''GetBackers'' assists a person in a hospital, not only does the head nurse assume he is a woman, she thinks he is a trainee, makes him wear a nurse's uniform, and takes his clothes.
** Ren also mistakes him for a girl, and is in turn mistaken for a guy by Shido. Amon goes so far as to hit on him.
** On many occasions, main characters have been peeping on what is supposedly a girl bathing, approached a "girl" from behind, or otherwise been completely blindsided when they see the face and [[UnsettlingGenderReveal realize that they've been attracted to Kazuki]].
** Major spoilers: [[spoiler:the end of the manga reveals that the GB world is an AI simulation with Infinity Tower as its conduit, explaining the superpowers the characters have. In the "real world", Kazuki really is a female, and is married to Jubei, bearing his child.]]
* Oddly enough, the ''Anime/YuGiOhGX'' dub makes several jokes about this in the case of Professor Chronos/Crowler:
-->"I didn't know he was a doctor."\\
"I didn't know he was even a dude."
* Tokiya Mikagami in ''FlameOfRecca''. A death glare awaits those who think he's actually a girl in disguise.
** Even more explicit in the anime than in the manga. When a guy identifies the only teenage boy around as being [[{{Tomboy}} Fuuko]], an enraged Tokiya shouts, "You idiot! I bet you thought I was a girl!"
* Akira Shiraishi in ''AiOreLoveMe'', the 'princess' of his all-boys school, and considered a girl even by his brothers. Also dating the [[{{Bifauxnen}} 'prince']] of an all-girls school, Mizuki Sakurazaka. This generally leads to people around them being shocked when they go out on a date and overhear Akira calling Mizuki his girlfriend or Mizuki mentioning Akira's her boyfriend.
* Loran Cehack from ''Anime/TurnAGundam'' is effeminate enough that, in masculine clothing, Guin Lineford called him "Laura" (also used by the Earth Militia and Dianna Counter when referring to him). He also [[WholesomeCrossdresser crossdresses rather convincingly]].
** Lineford himself lampshades the name, saying it suits Loran better. It's turned into an important plot element as the enemy (and most of the militia) are convinced the "White Doll's" pilot is female.
** Rumor has it that Loran's design was Tomino's WriterRevolt against the execs not letting him have a female main character.
* In ''AnatoliaStory'', Yuri mistakes a guy named Tito for her little sister Eimi. Funny, since Yuri herself is a {{Bifauxnen}}.
* Husky the fishboy, from the manga ''Manga/PlusAnima'', is so girly in appearance, even the reader isn't sure of his gender until he complains about being forced to dress like a girl. When he's introduced, he's a circus attraction... the Mermaid Princess. Characters frequently mistake him for a girl, and his friend Nana at one point becomes convinced that he's a girl in disquise due to his appearance and the fact that he's more girly than ''she'' is. Poor Husky is forced to prove his masculinity by getting naked and showing a horrified Nana his manly bits. As it turns out, the reason he [[HeManWomanHater doesn't care much for girls]] is because of how much he was teased for looking and acting like one as a boy.
** A side character even ''falls in love with him'' after Husky saved him from drowning... poor guy thought he was, well, the mermaid princess.
** A group of teenage boys invite him to come 'play with them', thinking he's a girl. One mentions 'she' is a bit young, but apparently the leader "likes [his girls] young". Even after Husky [[BerserkButton attacks them in rage]] they don't realize he's a boy.
* Souji Okita in ''PeacemakerKurogane'' looks eerily like a woman. Other Shinsengumi members [[LampshadeHanging lampshade]] it a few times by reproaching to him that he walks like a woman, acts like a child and is girlishly pretty that he resembles a young girl. That, and he almost never carries a sword around when he's off-duty.
** Also, Suzu. Especially after he starts wearing makeup and revealing clothes in the sequel manga. Even the other characters in the series comment on how beautiful he is.
** There's also Susumu. He often cross-dresses (quite convincingly) to gather information.
* Kurama from ''Manga/YuYuHakusho''. In the last episode, some girls in a train station mistake him for Kuwabara's girlfriend (which seems strange, since he is quite tall, flat-chested and broad-shouldered).
** This is even funnier in the manga, due to the fact that Kurama briefly starts to lose his temper. When Yusuke later asks him to help nab a monster at a girls' school, Kurama bitterly asks, "Should I wear a disguise, or shouldn't I bother?"
* Kagemiya Sen from the ''{{Kekkaishi}}'' manga can be easily mistaken for a female due to his face shape and hairstyle. This is also noted by the other characters in the manga itself, to Sen's displeasure.
* ''NaruTaru'''s Norio "Nori-rin" Koga has very feminine looks and is often mistaken for a girl.
* Rei in ''FistOfTheNorthStar'' actually takes advantage of this - he disguises himself under a sheet, leaving only his very feminine eyes showing, and then kills the bandits that try to take advantage of him.
* Yellow Belmont in ''GenesisClimberMospeada'' disguises himself as a female Pop singer to avoid detection by the Inbit. His natural appearance is so feminine, however, that in one episode while sunbathing almost completely naked, he is still mistaken for a woman by a tribal youth seeking a wife.
* Canute in ''VinlandSaga'' is initially mistaken for a girl once he removes the helm hiding his face, and though the confusion gets cleared up fairly quickly, Thorfinn continues to use the insulting nickname "Princess" for a bit, and Thorkell's men once make a crack that if Thorkell is the avatar of Thor, Canute must be the avatar of Freya.
* Hibiki Tokai from ''{{Vandread}}'' was mistaken for a young girl once by another man.
* Kazumi in ''GargoyleOfTheYoshinagas''. That he looks like a girl is one of the things his little sister teases him about to no end. Still, he's generally a nice guy and even has a girl that has a crush on him.
* Chiharu, one of the minor characters in ''TheyAreMyNobleMasters''. Besides being frequently ignored (even more than Yume, who's already barely noticed by the other characters), Ren has to have his gender confirmed the first time they meet.
* Junior of ''[[Anime/ReadOrDie ROD the TV]]'' is pretty enough that one of the Paper Sisters invites him to be their younger sister, [[CloudCuckoolander so they can all play]] ''LittleWomen'' together. This... throws him somewhat.
* In [[Manga/AiKora Inoue]] [[Manga/MidoriNoHibi Kazurou's]] short story ''AoiDestruction'', the titular father of the main character is a 38 year-old man, yet looks like 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.]]
* ''Manga/PokemonSpecial'': Bugsy. Gold got a Bridget dropped on him real quick.
* Envy from ''Manga/FullmetalAlchemist'', who is male in the 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.
* Ranewater Calder from ''ZombiePowder''. It didn't help that he's the leader of a gang called the "Ash Daughter Gang"...
* ''Manga/HayateTheCombatButler'''s Hayate Ayasaki has a face girly enough that both Nagi and Maria are occasionally compelled to [[DraggedIntoDrag make him play dress-up for them]]. The result of those projects sends the {{Moe}} factor of the show through the roof.
* 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.
* Tooru and Yuujirou in ''Manga/PrincessPrincess'' frequently get asked out by other guys (when not in their princess garb). The aforementioned two have also stated that when Mikoto is standing next to his girlfriend, they look like two beautiful girls instead of a guy and his girlfriend.
* ''Manga/BlackLagoon'': In the omake episode ''Boys and Girls'' (in which everyone is genderswapped to their opposite genders), Revy (who gender-swapped to male) looks much like his original female version, such as the clothes & hairstyle, which causes Rock (who gender-swaped to female and has gone insane because everyone is gender-swapped) to believe that Revy is still a woman, but Revy admits to her that he is a guy and proves it by [[UnsettlingGenderReveal taking off his shorts and showing Rock his genitalia]].
* Andromeda Shun from ''Manga/SaintSeiya'' gets this a lot. His own older brother fell in love with a girl who was identical to Shun, "except for her gender and the color of her hair." It doesn't help that his (pink) armor, at least in the first story arc, appears to have breasts, or that one of the reasons why Esmeralda became Ikki's MoralityPet was because she looked ''exactly'' like a blonde Shun. Ikki himself told that to her face!
-->'''Esmeralda:''' Ah, Ikki. Sorry... did you think I was your little brother again?\\
'''Ikki:''' ... Yes. You two look identical! The only differences are your hair and eye colors.
* ''Manga/TheFiveStarStories''' Amaterasu dis Grand Grees Eydas IV and his sort-of honorary nephew [[ArtificialHuman Maximum HOLTFORS Ballanche Kaien]], Duke of Fates. The guys could win any [[AmbiguousGender androgyny contest]] just by showing up, and [[UnsettlingGenderReveal surprising]] unsuspecting males is a RunningGag for Amaterasu when he goes to [[KingIncognito fool around incognito]]. Hell, there was a moment when Amaterasu was impersonated by a full-on woman, and nobody noticed.
* After ArtEvolution, ''Manga/KatekyoHitmanReborn'' has suddenly started getting a bunch of them, including the protagonist. Chief offenders include Kikyo and Daisy of the [[spoiler:Real Furneral Wreathes]]. Only in the latest chapter has the translator been certain that Kikyo is male and no one can be certain if Daisy is this or a {{Bifauxnen}}.
* Hideyoshi from ''LightNovel/BakaToTestToShoukanjuu''. 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 running gag, and b) Hideyoshi gets most of the FanService of the series...in what would be extremely potent ''female'' fanservice moments, if not for Hideyoshi being, er, not female. StupidSexyFlanders ensues.
* Shinji from ''Anime/NeonGenesisEvangelion'' is essentially a GenderFlip of [[NadiaTheSecretOfBlueWater Nadia]] (see [[http://wiki.evageeks.org/Image:Sadamoto_nadia-shinji.jpg here]] for notes from [[WordOfGod Sadamoto himself]]). He was described by Sadamoto as looking like "a boyish young girl" (more evidence [[http://i528.photobucket.com/albums/dd325/Synapsidia/EVA/048272545b0140dfe444054e96364e821.jpg here]]), and was made as such to distinguish him from the mecha heroes at that time. Shinji's feminine facial features are brought up by Misato in the first episode, and during the eighth and ninth episodes he's made to look like a girl from nothing more than [[http://i528.photobucket.com/albums/dd325/Synapsidia/EVA/FemmeShin1.jpg a wardrobe change]].
** One of the official games that had its scripts designed from interviews with Anno also had Fuyutsuki say that Shinji looked just like Yui and then [[http://www.youtube.com/watch?v=r26VFYHj1dY&feature=related crossdress Shinji]] for the role all while saying how beautiful "she" looks; Fuyutsuki's actions soon become [[{{Squick}} overtly sexual]].
** Shinji and Kaworu also make [[AttractiveBentGender rather pretty girls]] with little more than a hair and eyelash change (and breasts) in the [[http://www.youtube.com/watch?v=5N_18EljyPk GenderFlip version of episode 24]], longer haired Shinjiko ends up looking like a young version of Yui.
** The issue is not helped by [[BridgeBunny Maya]], who is essentially Shinji in a female officers uniform. And female, obviously.
* Mumu Momoyama from ''Manga/ChocoMimi'' gets mistaken for female by both Choco and Mikachin when they meet him. He does occasionally wear skirts, and once dressed as a maid to advertise the class cafe, but he doesn't like being mistaken for a girl. Mikachin does assume he's a SweetPollyOliver once though.
* ''BlackBird'' has Kyo, whom Misao mistakes for a pretty girl upon seeing him as an adult.
* Finnian and Ciel from ''Manga/BlackButler''. Joker even had to ask if Ciel was a boy to make sure.
* Miller from ''KaguyaHime'' much to his dismay.
* Kenshin of ''RurouniKenshin'', who was based on a real historical figure who used his feminine appearance to his advantage, getting up close to his targets so he could assassinate them and hiding out in brothels after a kill.
* Hinata (Hina) Omori of ''Manga/DesireClimax'' looks just like his beautiful twin sister Mio Omori.
* In ''Anime/CodeGeass'', Lelouch (in one picture drama he's made to look prettier than the girls simply by putting on an ElegantGothicLolita dress).
* Frequently done in Kaori Yuki manga, not just in terms of art, but as part of the storyline.
** In ''CountCain'', the only thing Cain needs to do to convincingly crossdress is to wear a wig. He managed to fool a man into thinking he is high class call girl once, even though the man was literally inches away from his face.
** In ''AngelSanctuary'', the only thing Rosiel needed to do to fool mooks into thinking he was a woman was to ''talk in falsetto''.
** Lucille, the vocalist in the manga Grand Guignol Orchestra, is often mistaken for a woman.
* A lot of guys from ''SaiunkokuMonogatari'' but especially Sa Sakujun with his long pink hair.
** In the manga, Ko Kijin wins a men-in-drag contest basically by showing up.
* Yukinari from ''Manga/GirlsBravo''. In Season 2, Episode 6 he was made to look like a girl with a wig, a girl's outfit, and fake breasts. His disguise was so convincing that even the entire audience and Fukuyama (who hates guys) thought he was a pretty girl. And Fukuyama didn't realize Yukinari was actually a boy until after he [[CrotchGrabSexCheck grabbed his crotch]].
* Historical Japanese figure, Nasu no Yoichi, from ''Manga/{{Drifters}}'' is presented this way, to the extent that Toyohisa and Nobunaga both thought he was a girl at first.
* Nakameguro from ''SeitokaiNoIchizon''. It's enough to instill some StupidSexyFlanders moments in Ken in episode 12.
* In ''{{Hellsing}}'', Alucard's apparently [[AFormYouAreComfortableWith female form]] counts, as despite looking the part, he still retains his deep, obviously ''male'' voice.
* Wapourif from ''{{Simoun}}''. The people of his world are female until they turn 17, at which point they choose their adult gender, but the change isn't immediate. Wapourif hasn't been a man long enough for his big breasts to flatten out, and still wears his hair long. [[ViewerGenderConfusion One could easily be forgiven for thinking he was a]] WrenchWench.
* Titus from ''Manga/MagiLabyrinthOfMagic'' is so girly-looking that Aladdin actually gropes his chest when they first meet in order to make sure Titus is a guy. Turns out there's a good reason for his feminine looks [[spoiler:since he's an OppositeSexClone of a female Magi]].
* In ''Manga/NatsumesBookOfFriends'', Natsume Takashi's most defining physical characteristic is his [[IdenticalGrandson uncanny physical resemblance to his grandmother at that age]]. While humans don't tend to mistake him for the opposite gender (except for that one time where [[http://i726.photobucket.com/albums/ww262/CapZiggy/natsumetrap.jpg he was possessed by a female Youkai]] and started giving his male friends ''[[StupidSexyFlanders thoughts]]''), {{Youkai}} seem to do it all the time, and according to Madara, the vast majority of Youkai do not make a distinction between genders.
* Pre-GenderBender Hazumu of ''KashimashiGirlMeetsGirl''. Yasuna, who DoesNotLikeMen, accidentally mistook him for a girl when he was still a "he".
* Mizuho of ''OtomeWaBokuNiKoishiteru'' is ''very'' pretty even when not cross dressing as a girl.
* Agito/Akito in ''Manga/AirGear''.
** In chapter 279, while fighting Agito, the girlish loli Shalott reveals to Agito that [[UnsettlingGenderReveal he is actually a guy]].
* In ''Webcomic/AxisPowersHetalia'', several people thought that China was a girl, him with his ponytail and all. Well, it's not that hard to believe [[http://i824.photobucket.com/albums/zz169/JulieTF2/Axis%20Powers%20Hetalia/4540851.jpg with]] [[http://i327.photobucket.com/albums/k451/anekisee_album/axis%20power%20hetalia/402869.jpg pictures]] [[http://fc03.deviantart.net/fs41/f/2009/010/c/a/caa4ee10ed9b96bd47d1b9f519e044ac.jpg like]] [[http://fc07.deviantart.net/fs40/f/2009/055/7/4/APH_China_version_Huggy_Pillow_by_JikokuNoRei_sama.jpg these.]] [[http://3.bp.blogspot.com/_W-TWZHRT-Fs/TRtMwOppTdI/AAAAAAAAAII/QK3FBhiJLDY/s1600/nihao_china.jpg It's no wonder]] [[http://images4.wikia.nocookie.net/__cb20100317175501/hetalia/images/6/6b/Hetalia_China_CD.png the fans are]] [[http://blog-imgs-38-origin.fc2.com/h/i/m/himaruya/nihao_china.jpg confused]].
** Lampshaded by the creator:
-->The only female member of the Allies...''not''.
** Chibitalia (young North Italy). Many nations, including his caretaker Austria, were convinced he was a girl and the Holy Roman Empire even [[HoYay fell for him]]. Until Italy reaches puberty and his voice changes.
** [[AgentPeacock Poland]] already looks girlish, and then he talks in a schoolgirl dialect (translated to ValleyGirl in English) and when he feels like it, [[WholesomeCrossdresser crossdresses]]. When they were children, Prussia pointed out that Poland looks like a girl and because the Teutonic Knights had a vow of chastity, [[ItMakesJustAsMuchSenseInContext he had to touch his balls]]...Poland wasn't up to it.
* A few characters in ''UragiriWaBokuNoNamaeWoShitteiru''. Most notably Yuki who's even told he looks like a girl by other characters. Which is quite understandable as he [[spoiler:has been a girl in all of his previous lives.]]
** And in episode 14, Sodom, once he reveals his human form.
* Daisuke Niwa from ''DNAngel''. He was made to dress up as the princess in a play and made a ''very'' convincing girl with just a wig and dress. On one occasion one of his friends even comments on how girly he looks.
* ''OuranHighSchoolHostClub'' [[PlayingWithATrope plays with this]], in that Haruhi would fall into this perfectly... and does in the eyes of the Host Club's customers. Except, [[WholesomeCrossdresser she actually]] ''[[WholesomeCrossdresser is]]'' [[WholesomeCrossdresser a girl]].
* Shun in ''HereIsGreenwood''. As a practical joke several older residents of the dorm convince the main character (who is Shun's roommate) that Shun is in fact a crossdressing girl. This deception holds until Kazuya runs into Shun using the urinal.
* ''ShugoChara'' has Nagihiko, [[spoiler:[[WholesomeCrossdresser otherwise known as Nadeshiko]]. Yup, [[YamatoNadeshiko that Nadeshiko]]]]. [[http://www.zerochan.net/src/zerochan.Fujisaki.Nagihiko.55231.jpg This is a guy, believe it or not.]]
** Tadase Hotori, too.
* Rune in ''KarakuridoujiUltimo''. It's actually lampshaded; he ''was'' a girl in his past lives.
** If you prefer to believe the Doji actually have genders (they are supposed to be robots) then Ultimo, Desir, Jealous, and most especially Sophia and Service all count (the former for his feminine name, and the latter for being a CaptainErsatz of [[ShamanKing Tamao]])
* ''{{No6}}'': Nezumi. He makes a living by performing in Shakespeare plays. In episode 5, he was playing a girl. In episode 1, Shion even states that he looks like a girl.
** Also, Dogkeeper.
** Shion too. He's very pretty, has a face similar to Safu (a girl) and in chapter 6 a guy hits on Shion and tells him that he's "very pretty".
* The titular character of ''KunisakiIzumoNoJijou'' looks like a girl and is often mistaken as such. Because of that, he is also invariably assigned as an ''onnagata''[[note]]male actor playing female roles[[/note]] in the kabuki plays organised by his family's troupe, much to his chagrin.
* Suriou from ''Manga/KamisamaKiss.'' Some of the other characters even lampshade it when they remark that he is prettier than the female lead, Nanami.
* Minoru in ''Manga/AKB49RenaiKinshiJourei'', which inspired him to cross-dress and participate in the same auditions as his crush to secretly provide her some moral support.
* Mizuki, the main character of ''Manga/BokuGirl'', is a guy, but he looks so much like a girl that about everyone has mistaken him for one his whole life. He has even received several love confessions from guys who may or may not be demotivated by his real gender, to his great dismay. To make matters worse, the goddess Loki decides to play a prank on him and [[GenderBender turns him into an actual girl!]]
* In ''Pump Up!'' the protagonist mistakes a male classmate for a girl. It doesn't help that their uniform is androgynous, aside from girls wearing skirts and boys wearing slacks, and he's short for a boy. His feminine looks have made [[EvenTheGuysWantHim him popular with guys too]].
* Ranmaru Fujieda from ''Manga/HaikaraSanGaTooru'', being a kabuki artist and also doing acting training.
* [[spoiler:Seiji Asou]] from ''Manga/DetectiveConan'' is strong enough in this department that his actual gender was not questioned after being on a [[spoiler:HarmlessLadyDisguise]] for two years.
* Yuuta of ''LightNovel/ChuunibyouDemoKoiGaShitai'' looks quite feminine, according to a few characters and, in the light novels, himself.
-->'''Isshiki''': "Hmm, it’s disappointing! Why weren’t you born as a girl?! Ah, but maybe you’ll do if we put you in female clothing... how about it?"
* ''Anime/TonoToIssho'': [[{{Moe}} Motochika]], to the extent that he's voiced by MamikoNoto and his retainers refuse to accept he's a boy, making him wear a miniskirt and fantasising about marrying him.
* Count D from ''Manga/PetShopOfHorrors'' is often mistaken for a woman, to his great annoyance. Probably doesn't help that his traditional Chinese clothing looks rather ambiguous.
** Papa D (and Sofu D) [[spoiler:being genetic copies of him of course look the same]]. Papa D also has long, flowing hair to make it even better.
* In ''LightNovel/ACertainMagicalIndex'', Last Order asked Accelerator if he was a boy or a girl because she couldn't tell.
* Ruka (sometimes called Rukako) from ''SteinsGate'' is incredibly effeminate, and [[WholesomeCrossDresser frequently cross-dresses to complete the illusion]]. [[LampshadeHanging Lampshaded]] by Rintaro when Ruka is introduced; he makes a series of flattering descriptive statements, followed by "But he's a dude".
-->'''Rintaro (narrating):''' Ruka: the embodiment of feminine grace and charm...also a total dude…"
* Nagisa from ''Manga/AssassinationClassroom'' confused many readers into think he's a girl. At one point it's lampshaded when the class goes swimming, and a couple girls notice he's in male swimwear.
* In the ''Anime/{{Free}}'' drama CD it's mentioned that Rin has a pretty face and looks very good in a maid dress (His own sister calls him pretty.)
* Played with in ''Manga/UQHolder''. The supposedly male Kuromaru is extremely girly and gets mistaken for a girl and called "miss" by about every other character. In fact, it's [[AmbiguousGender left ambiguous]] for some time whether Kuromaru is just a really feminine male or [[{{Transsexual}} a biological female who identifies as male]]. However, while Kuromaru isn't lying when claiming not to be a girl, "he" is not actually a "dude" either. Turns out Kuromaru has NoBiologicalSex: the particular breed of demons he is descended from do not become male or female until 16 years of age, at which point they make a conscious decision which to become. Kuromaru is currently leaning towards male (hence why he identifies as such), but hasn't reached that age yet. To make things more complicated, Kuromaru is beginning to think about becoming female due to developing a crush on the male main character.
* ''LightNovel/KanojoGaFlagOOraretara'': 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 blazer) is the only way anyone could see that he was actually a boy.
* ''Manga/WaratteSotomuraSan'': In a flashback from when the Sotomura siblings went to a store to buy yukatas, each one was given something for the other's gender.
[[/folder]]

[[folder:Comic Books]]
* Korbinian ("Bini") from ''ComicBook/{{Mingamanga}}'' is a Heavy Metal fan and has the hair. Also, the teacher mistakes "Korbinian" for "Korbinia".
[[/folder]]

[[folder: Fanfiction]]
* In [[http://www.fanfiction.net/s/6480316/1/The-World-in-Black-and-White The World in Black and White]], Kaizo (Kon's name in this verse) hits on three girls in his first appearance. The last "girl" is actually Uryu. Who promptly [[BerserkButton snaps]] in response.
* The ''Franchise/{{Pokemon}}'' Send Your OCs fanfic ''FanFic/PokemonTakeTwo'' has given us Trevor, who's femininity is {{Lampshaded}} by Raion when she mistakes him for a girl, and Alex, who Raion ''almost'' mistakes for a girl.
[[/folder]]

[[folder:Film -- Animation]]
* This is Francis the male ladybug's shtick in ''WesternAnimation/ABugsLife''. He has a very feminine face as well as a very masculine voice. This is lampshaded a couple of times; for example, when we first meet him, two bugs in the audience start hitting on him when he performs.
-->'''Francis:''' ''So'', [[TertiarySexualCharacteristics being a ladybug automatically makes me a girl]]! Is that it, flyboy?! Eh?!\\
'''Flies:''' [[UnsettlingGenderReveal Cripes, she's a guy!]]
[[/folder]]

[[folder:Film -- Live-Action]]
* Angelica in ''Franchise/PiratesOfTheCaribbean: On Stranger Tides'' poses as Jack because he was the only (male) pirate she thought she could pass for.
* [[spoiler:Tobio]] in ''WildZero'' (although he ''might'' be a WholesomeCrossdresser).
* In the movie version of ''{{Hair}}'', the hippies crash a party and one of the partygoers comments on the "Negro with the two young ladies" (there was only one girl in the group; the "second" was presumably [[http://www.fanpop.com/clubs/hair-film-musical/images/26211480/title/woof-photo Woof, who has long blonde hair and is clean-shaven]]).
* The '60s comedy ''WhatsNewPussycat'' opens with Peter Sellers, in a velvet suit and shoulder-length hair, arguing with his wife who accuses him of seeing another woman. She demands "Is she prettier than me?" He shouts "Is she ''prettier'' than you?! ...''I'm'' prettier than you!" (Note: for comparison's sake, he's nowhere ''near'' pretty.)
* Inverted in the film version of ''Film/DarkShadows''. During the party at Collinwood, Barnabas mentions that Alice Cooper is the ugliest woman he's ever seen, not realizing that he was looking at a man. (He was confused by the name.)
* ''A Flirt's Mistake'' (1914). Creator/FattyArbuckle and other men are enticed by a passing creature wearing high heels, a flowing gown, and shoulder-length hair. Then he sees the person's front, and discovers the person is actually a bearded rajah. [[BerserkButton Who does not appreciate the attention.]]
* There is an instance used in ''The Case Of The Mukkinese Battle Horn'' but first heard in the radio program ''TheGoonShow'' in which Peter Sellers (in the short film, Harry Secombe in the radio show) is noticeably aroused by the veiled belly dancer in a seedy club who goes over to him and after calling "her" a beautiful creature etc., he asks what causes '"her" to dance in such a den of sin?' "she" lifts her veil revealing "her" to be Eccles (Played by Spike Milligan) with the line "I've got to make a living too you know!"

[[/folder]]

[[folder:Jokes]]
* A cabbie picks up a nun. She gets into the cab, and the cab driver won't stop staring at her. She asks him why he is staring. He replies, "I have a question to ask you, but I don't want to offend you." She answers, "My son, you cannot offend me. When you're as old as I am and have been a nun as long as I have, you get a chance to see and hear just about everything. I'm sure that there's nothing you could say or ask that I would find offensive." "Well, I've always had a fantasy to have a nun kiss me." She responds, "Well, let's see what we can do about that: #1, you have to be single and #2, you must be Catholic." The cab driver is very excited and says, "Yes, I am single; and I 'm Catholic too!" "OK" the nun says. "Pull into the next alley." He does, and the nun fulfills his fantasy with a kiss that would make a hooker blush. But when they get back on the road, the cab driver starts crying. "My dear child,” said the nun, “why are you crying?" "Forgive me Sister, but I have sinned. I lied. I must confess, I'm married and I'm Jewish." The nun says, "That's OK, my name is Gary and I'm on my way to a Halloween party."
[[/folder]]

[[folder: Light Novel]]
* ''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 do ''real'' [=PKs=]), he now has to go around looking like Literature/SnowWhite!
[[/folder]]

[[folder:Literature]]
* Most males in the ''AnitaBlake'' series fit this trope except for Richard and a couple of others. Most of them are swooningly subservient, have feminine faces, slender bodies and long flowing hair.
* [[Literature/RealmOfTheElderlings The Fool]] in RobinHobb's works. [[spoiler:He even spends a few years passing as a woman]], and for most of the series the Fool's exact gender is unknown, until the final book of The Tawny Man series, where it is revealed that the Fool is [[spoiler:actually male.]]
** Well, hir belongs to a non-human species and some of hir physical attributes are continually changing (skin and hair colour). It is entirely possible that zee physically changes hir sex in intervals (it seemed more like zee was genuinely thinking of hirself as female-gendered for a time, not just pretending), or that hir physical sex wasn't determined until the last trilogy, considering zee was still adolescent before that.
* Lani Garver, from ''WhatHappenedToLaniGarver''. In fact, although [[spoiler:the narrator finally just refers to Lani in the masculine form, the issue is never actually resolved]].
* There's an [[PlanetOfHats entire species of these]] in Creator/AlanDeanFoster's ''Taken'' trilogy. When they talk, however, [[CuteButCacophonic they sound like garbage disposals]], as fits their combination of [[ProudWarriorRace an absolute sense of honor and a fondness for killing]].
* Nakajima, protagonist of the ''Literature/DigitalDevilStory'' series, is described as handsome in a feminine way. Specifically used as a taunt at one point.
* [[{{Nightrunner}} Seregil]] ''unintentionally'' manages to have a very straight man fall in love/lust with him using only a very modest dress, a little make-up, and his acting skills. (He already has a slim body, long hair, and apparently no facial hair growth.) He spent many days in that disguise surrounded by the same people on a cramped ship, and nobody noticed. His apprentice also developed a bit of a crush on him, and later unconciously choses a female prostitute who looked like Seregil in drag. [[spoiler: Of course, later it turns out that the kid is bisexual and just hadn't realised it yet.]]
[[/folder]]

[[folder:Live-Action TV]]
* Vince Noir of ''TheMightyBoosh'' is mistaken for a woman (or more specifically, as his [[HeterosexualLifePartners friend]] Howard's wife or girlfriend) in nearly every episode. He addresses his oddly compelling androgyny himself in the episode "Party": "Of course you [fancy me] -- all men do! I'm the confuser! 'Is it a man? Is it a woman? I'm not sure if I mind!'"
* Dennis Finch in ''JustShootMe'', though he is more often confused for being gay.
* The ''{{CSI}}'' episode "What's Eating Gilbert Grissom?" features a guy killed after he is mistaken for the ''female'' victim the murderer had already picked out. The murderer did have vision problems though, due to bad laser surgery, but not confusing your victims is Serial Killer 101.
* An episode of the German police procedural ''Series/{{Tatort}}'' had a short scene from a rapist's point of view while he was looking for a new victim. The camera lengthily gazed over several longhaired beauties, among them one which caused the POV to rapidly shift to another when ''he'' turned around.
* ''TimAndEricAwesomeShowGreatJob'' had a whole song about a man whose ''footsteps'' sounded like those of a woman.
* An episode of ''MadAboutYou'' had Paul and his cousin first mistaking an obese "woman" as pregnant - and when correcting for that mistake, discovering it was a man. After it was solved, they call the waiter who asks "And the lady?".
* While Kurt from ''{{Glee}}'' doesn't ''look'' like a girl per se (though he's {{Bishonen}} enough that him doing drag isn't hard to picture), he certainly sounds like one: the second thing he usually has to say when answering the phone is "No, [[MissingMom she's dead]], [[BlackComedy this is her son]]." It's been lampshaded a bit, like like Sue calling him "lady face" and when the mean jocks in theatricality mentioned that they couldn't tell the difference between him and girls.
* ''Series/ChappellesShow'': During Charlie Murphy's True Hollywood Stories skit about {{Prince}}, Charlie Murphy remarks how Mickey Free, a member of Prince's crew, looked like a girl.
-->When he joined the group, I heard mad cats like, "Yo, Shalamar got a new girl in there, man, bitch fine like a motherfucker." They was talking about Mickey Free, man, okay? Mickey Free is not a girl."
* ''NoahsArc'': Even aside from the effeminate clothes, Romeo's physical features are remarkably feminine.
* ''TwoBrokeGirls'': Han remarks in one episode that a CampGay couple asked him if he was a "rice queen on the downlow"
-->'''Earl''': They think he's gay!
-->'''Max''': Huh... ({{beat}}) That's a step up; [[DeadpanSnarker usually people think he's a lesbian]].
** It happens again in "And the Pearl Necklace":
-->'''Sophie''': Where's that Asian lady who usually brings me my menu?
-->'''Caroline''': That's Han ... Han's a man.
-->'''Sophie''': If you say so ...
* In the ''Series/{{Bones}}'' episode "The Girl in the Mask", a doctor flies in from Japan to aid with the investigation and the team spends most of the episode trying to figure out his/her gender. Angela divines at the end of the episode through a very thorough hug that he/she is a man, despite the fact that the character was played by a woman.
* In ''Series/ThirtyRock'':
-->'''Bucky Bright''': I wandered the building all night. I didn’t run into another single living soul. Except one giant lesbian. Who is ''Conan O’Brien'', and why is she so sad?
* On ''Series/That70sShow'', Jackie uses makeup to glam up Kelso like DavidBowie. She's delighted with the results and chirps "You're prettier than Bowie!" ''He's'' pleased with the results and chirps "I'm prettier than ''you!''"
* Referenced in ''Series/AgentsOfSHIELD'' when the Asgardian woman Lorelei sees a $100 bill for the first time and thinks that Creator/BenjaminFranklin is a woman.
* On an episode of ''Series/TheBennyHillShow'', Benny is in a bar and attempts to pick up what he thinks is a long-haired woman. Benny approaches her and says "My wife doesn't understand me." The "woman" turns around, showing herself to be a long-haired man, and says "Neither does mine!"
[[/folder]]

[[folder:Manhwa]]
* ''Literature/{{Id}}''. Acknowledged oh so many times in-universe.
[[/folder]]

[[folder:Music]]
* Besides the TropeNamer, there's also Music/TheKillers song "Somebody Told Me"[[note]]"that you had a boyfriend who looked like a girlfriend that I had in February of last year"[[/note]].
* "And [[Music/{{Wings}} Jet]], I thought the major was a lady suffragette. '''[[WordSaladLyrics JET!!!]]''' ''[[EarWorm Woo-ooh-ooh-WOOH-ooh-ooh-WOOH-ooh-ooh!]]''"
* On the cover of their first album, the guys in Poison wore so much makeup that many thought they were girls.
* Oh, SHINee's Taemin... and Key for that matter.
* Ren, of the Korean boy band Nu'est.
* Youngwon, in the music video for ER.
* Luhan, of the kpop band Exo. This particular member also applies to the trope Even the Boys Want Him.
* Kevin from K-pop band U-Kiss.
* Heechul, of [[Music/{{Super Junior}} Super Junior]]. He also enjoys dressing in drag.
* Jonas Bjerre, lead vocalist of the alt-rock band Mew.
* Most ironic of all, Steven Tyler's face has become unexpectedly feminine since his recent plastic surgery/ies. [[http://i.realone.com/assets/rn/img/7/8/5/8/20898587-20898592-slarge.jpg Dude * does* look like a lady.]] (CarlySimon, to be specific.)
** Interestingly, even before the surgery, it had been noted that his daughters (particularly [[Creator/LivTyler Liv]]) were ''really'' good looking, despite taking after him--and [[UglyGuysHotDaughter he's always been noted to look rather like a troll]]. Perhaps his native features just look better on a woman.
* Davey Havok of the band Music/{{AFI}}, as seen in [[http://www.mitchclem.com/nothingnice/151/ this]] ''Nothing Nice to Say'' strip.
** He's manned up considerably as of the release of Crash Love (2009).
* [[{{Placebo}} Brian Molko]]. ''Incredibly'' feminine.
** Depends on the photo. Sometimes he looks indistinguishable from a woman, other times he looks like a dude in makeup, other times he looks... [[{{Bishonen}} somewhat hard to tell]], etc.
* Music/DavidBowie is usually more a case of EvenTheGuysWantHim. He doesn't look that feminine, but [[MemeticSexGod who really minds]]? But in the late sixties and early seventies, he looked ''[[http://s1208.photobucket.com/albums/cc367/martiansailor/?action=view¤t=younghat.jpg very]]'' [[http://s1208.photobucket.com/albums/cc367/martiansailor/?action=view¤t=ring.jpg feminine]] [[http://s1208.photobucket.com/albums/cc367/martiansailor/?action=view¤t=hands.jpg indeed.]]
** It's the reason he's often mistaken for Creator/TildaSwinton, who [[InJoke played his wife]] in the video for "The Stars (Are Out Tonight)".
** "Lady Stardust" from ''The Rise and Fall of Ziggy Stardust and the Spiders from Mars'' is about a male performer who is initially laughed at for his long hair and makeup, but charms everybody of ''both'' genders in the room by the end.
** Look at his video "[[http://www.youtube.com/watch?v=OHg4MhX2XMw Boys Keep Swinging]]". Those three girl backup singers? They're all David Bowie.
* Jeffree Star has made a career of looking 'fierce'. Many don't realise he's a boy for quite some time. See [[http://www.musicbanter.com/attachments/rock-metal/3504d1244030353-jeffree-star-jeffree_star59.jpg here]]
* Bill Kaulitz. [[http://www.teenidols4you.com/blink/Actors/bill_kaulitz/bill_kaulitz_1178474792.jpg Yep, that's a guy.]]
** [[http://www.flickr.com/photos/21394586@N04/2249376392/ Have some more]] [[http://www.flickr.com/photos/27236928@N07/2580924947/ to help you]] [[http://www.flickr.com/photos/fatonandbill_fans/2562902681/ make up]] [[http://www.flickr.com/photos/chijee/1019192135/ your mind]].
** It's even funnier when you imagine what the other members of the ''boygroup'' he's part of must be thinking of the guy. Seriously, one day he looks completely normal and then poof, suddenly mascara! By this point, "Bill" looks girlier than Madonna.
** Before he finally finished puberty, Bill Kaulitz of the german Rock Band [[http://www.budapestinfo.hu/noc/photos/Esemenynaptar/tokiohotel.jpg ''Tokio Hotel'']] was most of the time mistaken for a woman for both, his looks ''and'' his voice. (Styling himself like a J-Rock singer might have had something to do with it as well.) 90% of the bashing the band got (And there were whole websites dedicated to bashing that band) were actually targeted against Bill's androgynous looks, which supposedly gave "real men" in german showbiz a bad name.
** It's also worth noting that one of those bandmates is his identical Twin Brother, Tom. He had the same features, but manned up his look considerably with the use of piercings and long dreadlocks.
* [[http://tinyurl.com/jonnepretty Jonne Aaron]], singer of the Finnish band Negative. Quite possibly more feminine than Kaulitz.
** It's not so much that he was more feminine than Bill, it's just that his was a much more natural femininity. He didn't use half as much make up.
** He has since [[http://i78.photobucket.com/albums/j92/His69InfernalChemicals/jonne-aaron_puddles.jpg manned up]]... sort of.
* On the subject of Finnish musicians, Marko Laiho of the BlackMetal band Beherit has exemplified this trope on a few of their [[http://www.last.fm/music/Beherit/+images/22530689 early]] [[http://www.last.fm/music/Beherit/+images/2358236 photos]]
* Sebastian Bach of Music/SkidRow. Although the people being fooled were ''BeavisAndButthead'' so that's hardly conclusive proof.
* People still mistake the 100% pure man J-rocker singer {{Gackt}} for a chick (despite his deep manly voice, rock-hard flat abs and personality) -- it might have something to do with his [[http://i38.photobucket.com/albums/e137/Fenrisaconite/0011s5wz.jpg pretty]] [[http://i38.photobucket.com/albums/e137/Fenrisaconite/GacktCalendarCover2006.jpg factor.]] He himself has stated that he thinks he would lose in a contest for looking like a manly man, but that he'd kick everyone's ass in an androgyny contest.
** The cover for his recent single "Koakuma Heaven" [[http://i48.tinypic.com/qp2xwp.jpg certainly doesn't help things]] (However you can clearly see his Adam's apple).
** This was especially funny around the time his new movie "Bunraku" was announced with a picture of him next to Josh Hartnett. Many fans of Hartnett who saw the picture on forums made comments like "Wow! That asian chick is so pretty! Who is she? Is she his love interest in the movie?"
** This can also be applied to many other Visual Kei artists and J-rockers, often intentionally. Although in a the case of [[http://i38.photobucket.com/albums/e137/Fenrisaconite/mostbeautiful.jpg Miyavi]], he looks girly even without make-up, skirts and hair.
** It isn't just Miyavi who looks feminine even without trying. [[http://images4.fanpop.com/image/photos/16800000/Toshiya-dir-en-grey-16891660-500-333.jpg Shinya]] from DirEnGrey has to be the best example of that. Music/XJapan's [[Music/YoshikiHayashi Yoshiki]] is the same. It must be a drummer thing. As for Gackt- well, he doesn't seem to be mistaken for a woman very often really, but maybe that's because when he was at his most androgynous he was within close proximity to [[http://www.quizilla.com/user_images/N/nakiko/1044725843_2gacktmana.jpg Mana]], and that can distort perceptions a bit.
*** [[http://25.media.tumblr.com/tumblr_lpq84dVgxy1qkn41po1_500.jpg Hizaki]] of Music/{{Versailles}} is, hands down, the [[WholesomeCrossdresser most convincing crossdressers]] in the scene at present, [[OlderThanTheyLook to the point where people even get his age wrong]]. To repeat: he looks like a beautiful teenage lady despite being a man in his mid-thirties.
* Boy George, especially during the 80's.
** Mind you, no one would ever have mistaken him for a ''pretty'' girl. Three decades later, he looks more like the sort of person you'd cast in a movie as a female impersonator, if you wanted it to be played for laughs. Like [[http://robertpreston.tumblr.com/post/60187942903/robert-preston-in-full-drag-as-carole-toddy-todd Robert Preston]] in ''VictorVictoria'', or [[http://draglife.blogspot.com/2006/04/gene-hackman-in-birdcage.html Gene Hackman]] at the end of ''TheBirdcage''.
* Music/MichaelJackson spent some time between plastic surgeries looking exactly like his sister Latoya.
* [[http://images4.fanpop.com/image/photos/23600000/ryan-ross-ryan-ross-23686106-400-389.jpg Ryan Ross]] from PanicAtTheDisco. Every time he decides to grow facial hair life feels like a bizarro acid trip where nothing makes sense.
** There is a pic of him and his ex-girlfriend where they looked exactly like a lesbian couple. Also this [[http://i213.photobucket.com/albums/cc41/xxindigobubblesxx/hesheorly.jpg picture]] where he must have been at least 19. He looks like the young girlfriend of the guy he's in the picture with.
** [[http://s213.photobucket.com/albums/cc41/xxindigobubblesxx/?action=view¤t=msg-125132217155.jpg Spencer Smith]] (on the left). In his [[http://i213.photobucket.com/albums/cc41/xxindigobubblesxx/2zftpcl.jpg younger]] [[http://s213.photobucket.com/albums/cc41/xxindigobubblesxx/?action=view¤t=SSSH14-1.jpg days]] he often looked girlish which was compounded by the fact that he sometimes wore [[http://s213.photobucket.com/albums/cc41/xxindigobubblesxx/?action=view¤t=0046fa4g.jpg girls']] clothing and jeans and usually stands with his hip cocked. You can see it in motion [[http://i213.photobucket.com/albums/cc41/xxindigobubblesxx/2r4kh6ojpg.gif here]]. Now he still has a pretty face but usually covers it up with a [[http://i213.photobucket.com/albums/cc41/xxindigobubblesxx/3835976026_81cccaa38c.jpg beard]] that's fuller at some times than others and a bigger, manly figure, also at times. He still ends up looking like a [[http://s213.photobucket.com/albums/cc41/xxindigobubblesxx/?action=view¤t=SSSL08-1.jpg bearded]] [[http://s213.photobucket.com/albums/cc41/xxindigobubblesxx/?action=view¤t=001br601.jpg woman]] sometimes though.
** This applies to [[http://i382.photobucket.com/albums/oo265/Blossom_Morphine/brendonstandupstraight.jpg Brendon Urie]] as well, only exacerbated... um enhanced with his [[http://cdn.buzznet.com/assets/users12/fansatthedisco/default/brendon--large-msg-115712488662.jpg flamboyant attire]] to match Spencer's, and liberal use of [[http://img.skitch.com/20080412-83ki1bjkkw9385ihp79rbs7ert.preview.jpg stage makeup]].
** Especially made clear when seen in this [[http://i382.photobucket.com/albums/oo265/Blossom_Morphine/PanicAtTheDiscogroup.jpg group picture]], with only Jon Walker (the one in black) looking particularly masculine.
* [[http://25.media.tumblr.com/tumblr_mdwtnwcRAk1qi4wugo1_500.jpg Gerard Way]] from MyChemicalRomance also fits this trope [[http://25.media.tumblr.com/tumblr_m9rbd2bSZR1qlma2so1_500.jpg really]] [[http://25.media.tumblr.com/tumblr_me3oumntlz1rpu39bo1_250.jpg really]] [[http://media.tumblr.com/tumblr_m7i78lYl9C1rtfl4t.gif well]].
* The Hanson brothers in the band {{Hanson}} were jokingly referred to as the Hanson sisters for a long time.
* AdamLambert of ''Series/AmericanIdol'' is this on the cover of his self-titled album.
* Pete Burns of 80's SynthPop group Dead Or Alive. A WholesomeCrossdresser. Partial subversion in that his singing voice makes it quite clear he's a man.
* '''All''' of the members of Music/XJapan. [[Music/ToshimitsuDeyama Take]] [[Music/YoshikiHayashi a]] [[Music/HidetoMatsumoto look]] [[Music/TomoakiIshizuka at]] [[Music/HiroshiMorie their]] [[{{Sugizo}} pages]] if you don't believe us. Subverted, however, by [[Music/TomoakiIshizuka Pata]] when he grew a beard to look more masculine.
* [[http://www.last.fm/music/A+Skylit+Drive/+images/35557657 Michael Jagmin (center, redhead)]] of post-hardcore band A Skylit Drive. [[http://www.youtube.com/watch?v=Mu8hlO4vZy4 His voice doesn't help.]]
* [[http://img527.imageshack.us/img527/7799/rogertaylormr3.png Roger Taylor]] of {{Queen}} fell victim to this trope so often that he [[http://userserve-ak.last.fm/serve/_/65768/Roger+Taylor.jpg cut his hair in an attempt to avert it]].
* J-pop singer SHOWTA. NO ONE believes he's a guy the first time they see him. It doesn't help that he has a very high, girlish voice.
* The late Taiwanese singer Chang Yu Sheng, [[http://www.youtube.com/watch?v=8dNW07P6sfo who also sounded like a girl]].
* Almost every group in Johnny's Entertainment has one.
* Japanese guitarist Hizaki of Music/{{Versailles}}. He wears [[ElegantGothicLolita fancy dresses]] and [[http://26.media.tumblr.com/tumblr_lwoj86z6Tz1r8ffuao1_500.jpg really]] [[http://24.media.tumblr.com/tumblr_lx5z31pAo51r5rpeio1_500.jpg pulls]] [[http://24.media.tumblr.com/tumblr_lxg0mb8E901r9tiaxo2_1280.jpg it off]]. [[AuthorExistenceFailure Late]] bassist Jasmine You [[http://28.media.tumblr.com/tumblr_m2xyswREdi1r0g69ro1_500.jpg also]] [[http://25.media.tumblr.com/tumblr_m2hhh4fCLu1r0g69ro1_500.jpg fit]] [[http://25.media.tumblr.com/tumblr_m1eugxjGpd1r0g69ro1_500.jpg this]]. Other guitarist Teru [[http://28.media.tumblr.com/tumblr_lz5xfegtLM1qixq22o1_500.jpg falls]] [[http://24.media.tumblr.com/tumblr_lry8z8EgGR1qixq22o1_500.jpg into]] [[http://29.media.tumblr.com/tumblr_lkybbe1u4r1qixq22o1_500.jpg this]] occasionally.
* All the guys in ''Vidoll'' and most other VisualKei bands.
* Music/JustinBieber.
** "[[http://thephoenix.com/unsexy/2010/rate/?a=733 There is nothing sexy about 16 year old boys.]] (...) Even if that 16-year-old boy looks like TaylorSwift's little sister."
* Music/MarilynManson [[http://i.imgur.com/4zhPg2D.jpg at times]] (NSFW)
* Korean singer G-Dragon [[http://www.asianpopcorn.com/battle_images/Bigbang_s_leader_G_dragon_01052010074410.jpg definitely looks like a girl despite his lack of hair.]]
* Everybody in the Japanese heavy metal band DirEnGrey used to look like females at the start of their career, especially because of the makeup.
* The artist who painted the front cover of [[HallAndOates Daryl Hall And John Oates']] self-titled 1975 album (the one with "Sara Smile" on it) make them look [[http://en.wikipedia.org/wiki/File:Hallandoatesselftitledcover.jpg very effeminate]] against the duo's will, especially Daryl, which would lead to stories that the duo [[HoYay were gay lovers]]. Daryl would joke in their 1998 VH-1 ''BehindTheMusic'' episode that on the cover he looked like "the woman I always wanted to go out with".
* [[Music/PinkFloyd David Gilmour]] with his long hair and slightly effimite appearance did fall into this trope when he was younger.
* A lot of glam-metal bands in the eighties tend to fall into this category. Poison, Music/MotleyCrue, Hanoi Rocks...the list is endless.
* Petri Lindroos of Ensiferum. [[http://www.stars-portraits.com/en/portrait-8763.html SERIOUSLY]].
** And apparently, the lady in question [[http://media.tumblr.com/17d22290880ab8f7804aa5b4c03c1b00/tumblr_inline_mqdlizHXG21qz4rgp.png is Sissy Spacek]].
* William Beckett, mostly when he had long hair.
[[/folder]]

[[folder:Religion and Mythology]]
* In GreekMythology, Narcissus fell in love with his own reflection. Some say that he mistook it for a beautiful woman, while others say that he recognized himself. He was then turned into a flower that bears his name. This happened because he spurned the affections of a young man named Ameinias and a (female) nymph named Echo, who prayed to [[NamesToRunAwayFromReallyFast Nemesis]] for revenge.
[[/folder]]

[[folder:Theatre]]
* In ''Theatre/{{Jerusalem}}'', Ginger is mistaken for a woman by the Professor, though this is only because the former has long hair and the latter is a senile and possibly crazy old man. Nobody else has any doubts about Ginger's sex, which makes sense given that Mackensie Crook doesn't look much like a woman at all.
[[/folder]]

[[folder:Video Games]]
* Raiden, from ''VideoGame/MetalGearSolid2''. Like Rune, he got patted down, but in... er, a different area. By the ''US President''. It doesn't help that we're so used to visual representation of the male body as having no hips (they do, just not as pronounced as women) that Raiden is relentlessly mocked because of the figure-enhancing suit he wears. ("Hips Don't Lie" is a minor meme for male character models that look like they're just very flat women.)
** Then there's Raikov, from the follow up game ''VideoGame/MetalGearSolid3''. Raikov was created in response to the controversy surrounding Raiden following his replacement of Solid Snake as the main character. Hideo Kojima on more than one occasion has commented on Raikov's beautiful looks.
* ''Franchise/FireEmblem'' has a couple of these. The first one seen by Westerners was [[http://serenesforest.net/media/fe7illust/s/ruthea.png Lucius]] from the seventh game, ''Blazing Sword''. He's even mistaken to be a woman by [[GenkiGirl Serra]] in-game.
** Libra from ''VideoGame/FireEmblemAwakening'' gets mistaken for a woman by practically everyone who talks to him, due to not only looking but ''sounding'' very feminine. So much that some of them occasionally forget that he's a man, ''even after he points it out to them''.
* And then there's Kuja from ''VideoGame/FinalFantasyIX'', who is wearing the most feminine, {{Stripperific}} outfit imaginable (except for the codpiece...), has feathers in his long, flowing, luxurious hair, and is wearing ''lipstick and eyeshadow'', not to mention the feminine hips and waist. There's a reason he's the poster guy for the ''ViewerGenderConfusion'' page. Only ''once'' is this commented on in-story, when Queen Brahne calls him girly.
* Bridget from (no, not ''Videogame/GuiltyGear'') ''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.
* Felix in ''VideoGame/RadiataStories''. He has a male stalker who is [[UnsettlingGenderReveal shocked and appalled]] when it is revealed that Felix is male - yet continues to stalk him anyway.
* ''Franchise/TalesSeries'':
** Zelos Wilder from ''VideoGame/TalesOfSymphonia'' in spite of his masculine build. No doubt because of his long, wavy, red locks and wardrobe color of choice being [[RealMenWearPink pink]].
** Mithos is far worse as he looks almost like Colette. [[spoiler:Considering Colette was the result of controlling marriages over time in an attempt to create an almost exact body duplicate of Mithos' sister for the purpose of becoming Martel, this is justified.]]
** Yuri from ''VideoGame/TalesOfVesperia'' is quite attractive and a [[EvenTheGuysWantHim male NPC]] even comments on this suggesting he cut his hair [[StupidSexyFlanders to look more masculine]].
** Duke from ''VideoGame/TalesOfVesperia'' is also quite hot.
** Ion from ''VideoGame/TalesOfTheAbyss'', and Jade seems to have been with his official artwork.
** Richard from ''VideoGame/TalesOfGraces'' is often called "the prettiest girl in the game." The HoYay [[spoiler: and FoeYay]] doesn't help.
* Flea of ''VideoGame/ChronoTrigger'' is mistaken for a woman when he first appears. Of course, that he is apparently [[VillainousCrossdresser wearing a bra and a dress]] and talks like a flirtatious woman doesn't help in the slightest. Although surprised, he doesn't seem to mind even.
-->'''Frog:''' 'Tis no ordinary woman!\\
'''Flea:''' What the? I'm a guy!\\
'''Marle:''' THAT is a guy?\\
'''Flea:''' Male...female.....What's the difference? Power is beautiful, and I've got the power!
* Fierro of ''EternalEden'' fell in love with Jean despite Jean telling him that he's a man.
* Ranmaru Mori of the ''SamuraiWarriors'' series has a very feminine appearance, to the point that he gets mistaken for a woman in universe to the point of RunningGag status--he even "counts" as a lady for the purposes of {{Designated Girl Fight}}s. Amusingly, one of his battlecries from ''WarriorsOrochi'' is "I'm as dangerous as I am manly!"
* In ''VideoGame/WorldOfWarcraft'', blood elf males invoke this trope frequently. One post-Cataclysm quest, for instance, features a parody of a KnightErrant looking for [[DistressedDamsel damsels in distress]]. One of said damsels is a male blood elf, who dropped his [[LessEmbarrassingTerm "purse"]]...um "[[http://www.wowhead.com/quest=24705/damsels-were-made-to-be-saved crate]]" in the lake.
* As in other games, ''VideoGame/PokemonConquest'' portrays Ranmaru in this way, to the point where he ends up participating in an otherwise female-only tournament.
** Mitsunari is also portrayed this way.
** Not to mention some Pokemon themselves. Lopunny, Gardevoir, Aromatisse, Gothitelle/Gothorita, Machop line, Bisharp and a few more all look feminine even though they can be male.
[[/folder]]

[[folder:Visual Novels]]
* ''VisualNovel/AceAttorney:'': Jean Armstrong is an... odd, example. He's obviously male due to his beard and muscular arms, but his nature is so dainty and feminine that the judge actually asks him whether he's a woman. He even refers to himself as a 'girl' at times, which makes it even more confusing.
* '' VisualNovel/{{Clannad}}'': Kappei Hiiragi. Sunohara is still in denial, despite the fact that Tomoya told him that he had [[UnsettlingGenderReveal been fooled]]. The [[HoYay implications]] are not lost.
* [[WholesomeCrossdresser Hideaki Hakamichi]], Shizune's little brother from KatawaShoujo. [[AbusiveParents His dad]] seems about as sympathetic to his plight as he's to Shizune being deaf.
[[/folder]]

[[folder:Webcomics]]
* Jacob the Rag doll from ''{{Monsterful}}'', his long hair and shy personality make it even worse.
* Tedd of ''Webcomic/ElGoonishShive'', whenever he removes his OpaqueNerdGlasses. And even when he doesn't, "[[http://www.egscomics.com/?date=2003-04-29 he's just that androgynous]]" is the oldest RunningGag of EGS.
** Certain [[GenderBender habits of his]] don't help matters, though it's suggested that one of the reasons he does it is when he's a boy, his feminine face gets him mocked. When he's a girl, he's a [[StupidSexyFlanders hottie]].
** Noah is even worse. Elliot's reaction when [[http://egscomics.com/?date=2010-03-17 meeting him]] is "Who's this...guy? I think?"
** At one point, he magically dyed his hair pink and went to a ''TabletopGame/MagicTheGathering'' tournament. This [[http://www.egscomics.com/index.php?id=1854 drew attention]] from straight men at the tournament, although he seems to be under [[http://www.egscomics.com/index.php?id=1875 the assumption]] that anyone attracted to him is gay.
* Dan in ''DanAndMabsFurryAdventures'' with his long hair, fluffy wings, and robe, gets mistaken for a woman all the time. Sometimes he hates it, but sometimes he uses it to his advantage...
* ''Webcomic/PennyArcade'' had a running gag where Gabe kept mistaking game developer John Romero for a woman (despite Tycho's repeated corrections) because of his "long, flowing hair".
** [[http://www.penny-arcade.com/comic/2000/02/18/ They both made this mistake at least once]].
* Parodied in ''{{Insecticomics}}'' when MoralGuardian Lady Jaye attempts to make the 'naked' robots all wear censor bars. Override, who is female but has a gender-neutral body, taunts Lady Jaye by asking how many censor bars she needs. Lady Jaye eventually puts a censor bar on her groin but not on her chest, having decided that Override is male.
* Leslie from ''FlakyPastry'' has an [[GenderBlenderName ambiguous name]], dresses androgynously, works as a barmaid (complete with skirt and tube top) and is surprised when the girl he asks out thinks he is gay.
* In [[http://sidekickgirl.comicgenesis.com/d/20080730.html this]] ''SidekickGirl'' strip, Chris looks like a tall, skinny girl, but in the next strip is [[ShirtlessScene revealed to be a young man with very long hair]].
* [[http://www.sluggy.com/daily.php?date=971007 This]] ''Webcomic/SluggyFreelance'' strip invokes this trope thanks to an alien race where the males look an awful lot like human females. Rather than being [[UnsettlingGenderReveal grossed out that they were drooling over a guy]], Torg and Riff keep right on staring at his breasts. "Could you jump up and down for us, mister?"
* Cale from ''LookingForGroup'' is often referred to as "she" by Richard when the latter is still getting to know him, even after he's well aware that Cale is male.
* ''MyLifeInBlue'': "Your mom looks like a girl. Ooo."
* In ''GoldCoinComics'', Theo, whose job class (healer) is normally reserved for girls, is mistaken for a woman when Lance first meets him.
* [[FauxPas Randy]], who is male, once was miss April on a calendar.
* Kano, the main character of ''{{Kagerou}}''. The artist has made specific note of his "absurd girl hair".
* [[spoiler:Eutropia]] of ''WebComic/{{Amazoness}}'' -- it's actually a plot point.
* Chovek, a minor character in ''{{Inhuman}}''. The fact that he's [[PinkGirlBlueBoy pink]] doesn't help.
* Lampshaded heavily and hilariously in ''ChasingTheSunset'', as Leaf is ''so'' girly that it often takes ages for someone meeting him to realize he's a guy. But then, he's an elf, so [[{{Bishonen}} bishiness]] is pretty much par for the course.
* ''Webcomic/TheOrderOfTheStick'''s Vaarsuvius. [[AmbiguousGender May]][[ViewerGenderConfusion be]].
** Given the art style, pretty much ''everyone'' is of AmbiguousGender and we have to rely on clothing and how they're referred to by other characters to tell. V wears a wizard robe, so that's no help, and the other characters aren't any better since most of them have no idea what gender V is either.
* In spite of being an adult male well into adulthood, Vinci of ''Webcomic/VinciAndArty'' is often mistaken for being a female, at one point being mistaken for a pregnant woman in labor when pulled over by a cop. ItMakesSenseInContext.
** He often combines it with OlderThanTheyLook, too. How about being mistaken for a ''little girl?''
* Meet DubiousCompany's [[http://dubiouscompany.com/comics/2006/05/07 Elator]]. Later on a drunk Tiren braids his hair with [[ClingyMacGuffin magic hairties]] that won't undo. Most characters [[http://dubiouscompany.com/comics/2010/07/27 mistake him for female]]. Marty has [[SelectiveObliviousness problems]] with this [[http://dubiouscompany.com/comics/2010/11/09 revelation]].
* ''UnwindersTallComics'': Dr. Minivan, after losing his hair (for science), buys a wig to hide his baldness. The wig is so long that he gets mistaken for a woman. When this happens in a public restroom, he panics and hides in a stall, and tries to figure out how to get back out of the restroom without incurring further confusion. This takes so long that he grows a beard. Problem solved!
* ''Webcomic/{{Sunstone}}'' has Alan, who is so protective of what facial hair he has not even his wedding day could part him from it. Some of the characters have a vendetta to get the man to cross dress.
* Allen from ''Webcomic/AllenTheAlien'', who would't normally be this trope, is mistaken by the aliens for a girl; RR-TWTTW somehow think he resembles his daughter.
* ''Webcomic/{{Life}}'' has [[http://www.cha0sden.com/Life.php?comic=274 Edward's roommate]] [[http://www.cha0sden.com/Life.php?comic=275 Lex.]]
-->'''Lex:''' And yes, I am a guy.
* Lampshaded in ''Webcomic/MMBN7TheWorldTournament'', were Sean mistakes Viddy Narcy as a woman at first before their match.
[[/folder]]

[[folder:Web Original]]
* Izael from the ''Roleplay/TheGamersAlliance'' is often confused for a girl because of his looks.
* Axel from ''DemyxTime'' enjoys mocking Marluxia for this. Inverted when Demyx firmly believes that Larxene is a man.
* In the ''VideoGame/DissidiaFinalFantasy'' {{machinima}} "Real Men", there's a segment where Squall states, "Only a real man hangs out with the ladies." Cloud responds with, "You know that's a guy, right?" but Squall firmly states that it's a chick, until he finally decides to ask the man/lady in question, who is Bartz. Bartz replies, "Oh yes, I am male-I mean, FE-male." Squall's response?
-->Squall: "...Oh you're dead... *gunclick*"
* Phase, in the ''WhateleyUniverse'', looks and sounds so girly that he's given up and dresses in mannish girl's clothes that fit him, while he tries to find a way to change himself back to a manly guy. Even in pants and heavy coat, he still gets tabbed as a girl, much to his disgust.
* ''WebVideo/YuGiOhTheAbridgedSeries'' parodies this trend in ''Anime/YuGiOh'':
-->'''Marik''': [[YouFool Foolish fools!]] There are no women in Franchise/YuGiOh, only extremely girly men! And I am the girliest of them all!
-->'''[[SissyVillain Pegasus]]''': Keep telling yourself that.
** Marik and Bakura are frequently mistaken for a woman. Duke and Yami are very pretty like women as well.
* ''Roleplay/EquestriaChronicles'' has Shiloh, who looks like a filly and has been mistaken for one on multiple occasions.
* ''Roleplay/EquestrianLegends'': Beret Swirl invokes this trope to get free drinks.
* And while we're still talking about ponies, [=4chan's=] original character "Golden Brisk", who is CONSTANTLY mistaken for a female to his own chagrin, and spends most of his free time trying to make himself look "manlier" and failing hilariously. His love interest is his own DistaffCounterpart [[LadyLooksLikeADude Silver Breeze]].
* ''Website/GaiaOnline'''s Gino Gambino at one point looked very feminine despite the memetic "[[BigOlEyebrows Twinkie Brows]]"; the description for his collectible doll states that he's often mistaken for a girl. More recent manga updates featuring him have been making him a little more masculine, via ArtEvolution and an ImportantHaircut.
* In ''WebVideo/DeathNoteTheAbridgedSeriesKPTS4TV'' in DaChief's [[CloudCuckooLander warped perceptions]] Ryuk is a trap. Upon meeting him DaChief declares "goth girls are hot!" Also upon first meeting [[{{Bishonen}} Light]] Ryuk mistakes him for a girl:
-->'''Ryuk:''' [[MonsterRoommate Tell you what—I need a place to stay.]] [[FreudianSlip If you let me bunk with you maybe we can experiment together.]] W-with the Death Note. Not each other. You're a sick little girl, you know that?!
-->'''Light:''' But I'm a boy!
-->'''Ryuk:''' ''Riiight.''

[[/folder]]

[[folder:Western Animation]]
* ''WesternAnimation/HomeMovies'' - Brendon comes home to find his mom and her boss looped on wine. On seeing him the boss shouts "Well, look at you! What a perfectly adorable little young lady!". Brendon anxiously replies "Ah...well...I'm not so little...". Brendon is considered to be kind of girly by lots of folks, including his friends.
* ''WesternAnimation/{{Metalocalypse}}'': Skwisgaar Skwigelf is tall and thin, with long hair, large lips and very nice butt. He [[BerserkButton does not like it]] when you call him a lady.
* In an episode of ''WesternAnimation/JohnnyBravo'', Johnny is at the beach when he approaches what appears to a woman in a bikini, but as soon as the person turns around, it turns out to be a slender man with long hair in a speedo.
-->'''Johnny''': Whoa! I thought you were a chick!
* On ''WesternAnimation/TheLegendOfKorra'', Korra's [[CreepyTwins creepy]] HalfIdenticalTwin cousins Desna and Eska are introduced, and since they look exactly alike except for make-up on Eska (the girl), Bolin assumes they are both girls.
* The main joke of ''WesternAnimation/SheZow'' is the fact that the title character is a guy who has to dress like a girl due to the ring that gives him his powers. A TitleDrop of the tropes is done in the first episode.
* Edd from ''WesternAnimation/EdEddNEddy'' can be seen as this. In fact, [[spoiler:in the series finale, [[WesternAnimation/EdEddNEddysBigPictureShow Big Picture Show]], Eddy's brother mistakes him as Eddy's girlfriend.]]
* [[https://derpibooru.org/564162 Seabreeze]] from the ''WesternAnimation/MyLittlePonyFriendshipIsMagic'' episode "It Ain't Easy Being Breezies". The combo of pink hair, eyelashes, and the fact that the rounded muzzle is typically a trait of ''female'' ponies makes him look rather girly.
[[/folder]]

[[folder:Real Life]]
* Stylistically, it was common for painters in the 1700's to portray young boys as looking almost female. The fact that they wore dresses as children didn't help either...[[http://1.bp.blogspot.com/_CvDCiEFbNy8/SnScTK6yVII/AAAAAAAAKrc/kKf_UHs0szU/s400/1751++John+Hesselius+(1728-1778).+The+Grymes+Children-+Lucy+1743-1830,+Philip+1746-1805,+Jno+Randolph+1747-96,+Chas+1748-+.+Virginia+Historical+Society,+Richmond.jpg The second from the left is actually a boy]].
** Leonardo Da Vinci's tendency to do this has caused speculation about just who is sitting next to Jesus (is that the Apostle John or Mary Magdalene?) in his painting of The Last Supper.
** The wearing of trousers for young boys is actually more [[NewerThanTheyThink recent]] than many think, as smocks/kilts/skirts/dresses were more practical for a rapidly growing young boy as they were easier to adjust and refit than pants. In fact, the boy's first fitting for pants was considered a big thing for him and an important milestone in his growth, as it meant that the father took more of a role in his upbringing.
* Music/YoshikiHayashi, again - because he has been confused ''offstage'' in pics at events unrelated to his band.
* Mustapha Pasha, the Ottoman supreme commander.
* [[http://www.imdb.com/media/rm624728064/tt0355702 John Robinson]] in ''LordsOfDogtown''.
* [[http://www.cracked.com/article_15788_top-25-men-who-look-like-old-lesbians.html The top 25 men who look like old lesbians.]] So that's why MikeMyers hides behind so much make-up.
* In a [[TearJerker really truly depressing]] real life example, one of the victims of the real-life [[http://en.wikipedia.org/wiki/Monster_of_Florence Monster of Florence]] was a young male German tourist named Jens Uwe Rüsch, traveling with his also male friend Horst Wilhelm Meyer. It's believed that they were mistaken for the killer's more usual targets, a heterosexual couple alone in their car, because of Rüsch's slight build and long blond hair.
* [[Film/TheCryingGame Jaye Davidson.]]
* JamieCampbellBower. He played young Gellert Grindelwald, lover then enemy of Albus Dumbledore, in the last Film/HarryPotter films. However, it was never stated that Grindelwald was gay, too...
* [[Creator/ChrisCrocker Chris "leave Britney alone" Crocker]]. [[http://en.wikipedia.org/wiki/Chris_Crocker_(Internet_celebrity) No, seriously]]
* Somewhere between this and CrossDressingVoices: Haydn's Die Schöpfung (The Creation). The oratorio has three angelic soloists. Gabriel is played by a soprano.
* ''WesternAnimation/TheVentureBrothers'' co-creator Doc Hammer is self-admittedly a very feminine-looking guy. Ironically, he does the extremely masculine voice for Dr. Girlfriend. When asked at a con whether or not he would do Dr. Girlfriend despite her manly voice. Doc answered in the affirmative, then turned it around:
-->"Would you do ''me'' if I had a really sweet girl voice? I'm telling you, from behind, it doesn't make much of a difference!"
* Quite of few of the guys in [[http://www.youtube.com/watch?v=Q77sJT8O56E this news report]] on the "Teen Werewolves" phenomenon, especially their unofficial leader.
* German actor [[http://images.wikia.com/cinema/it/images/2/23/Sandro_Lohmann.jpg Sandro Lohmann]].
* Persian Crown Prince [[http://upload.wikimedia.org/wikipedia/commons/e/e1/Abbas_Mirza_Qajar_%28Art_Museum_of_Georgia%29.jpg Abbas Mirza Qajar]] did some very manly exploits, notably fighting the Russians during the Napoleonic Wars and afterwards and having 26 sons, but paintings of him have him with big doe eyes, rosy cheeks, and flowing dark hair. Even after he grew a thick, manly beard, he still was quite slender, and the tight robes he wore did not help.
* Seattle {{drag queen}} Jerick Hoffer (aka Jinkx Monsoon, eventual winner of the fifth season of ''Series/RuPaulsDragRace'') looks and sounds like a lady even when out of drag.
* The ancient Chinese strategist Zhang Liang was historically this. In Literature/WillOfHeaven, it even becomes a plot point.
* [[http://www.fmylife.com/love/245607?utm_source=fmylife&utm_medium=illustrated&utm_campaign=245607 This]] FML.
* Really, most guys who simply grow their hair out to shoulder length or longer can vouch for this trope getting invoked on them at least once, usually by random passerbys who just don't look hard enough.
* [[http://9gag.com/gag/a6wB92b This.]]
* Dutch speed skater [[http://www.nusport.nl/overig-sotsji/3703306/verweij-pakt-honderdste-plak-nederland-winsterspelen.html Koen Verweij]].
* Actor Daeg Faerch who is best known for his role as young Michael Myers in ''Film/{{Halloween2007}}''.
* NoelFielding looks androgynous at the best of times, and he can pull off a woman [[http://smg.photobucket.com/user/BasilBrush/media/Blog/180446_10150090688166910_539316909_6783401_6793048_n.jpg.html extremely]] [[http://33.media.tumblr.com/c1ed93c60e8f2424f33bfaa5a8d9e5ad/tumblr_n017567nD71qfqs3do4_250.gif convincingly]] if he wants to. His feminine appearance has been commented on numerous times, both in interviews/panel shows and in fictional works he appears in (his character on ''Series/TheMightyBoosh'' gets mistaken for a woman at least OnceAnEpisode and never even bats an eyelash).
-->'''Frankie Boyle:''' "To me, Noel looks like a raven that a wizard has turned into a very beautiful young lady."
* [[http://gorightly.files.wordpress.com/2008/09/610x.jpg Walter Mercado Salinas]] also known by his stage name "Shanti Ananda'', a Puerto Rican dancer, actor and writer, best known as a television astrologer.
[[/folder]]
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