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 Lady Looks Like a Dude, this trope involves male characters who are frequently mistaken for female (by other characters).
Not to be confused with:
Bishōnen (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)
Alto Saotome from Macross Frontier. Well, it generally happened offscreen, but his 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 andis a dead-ringer for his gorgeous Missing Mom, 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.
Lord Geppelnitch (or, rather, the human body he's possessing) from 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.
Samurai Deeper Kyo 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.
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.
Likewise Nuriko, though 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 Up to Eleven, to the point that he literally looks like a woman, complete with relatively large breasts and an attractive feminine figure. Even Word of God state that it's a dude in spite of his appearance. The only thing that makes him a male is that he has male genitalia.
Yu Kanda from D.Gray-Man 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 Dragon Knights 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.
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 Crowning Moment of Funny.
Shingo in the King of Brutes storyline in Violence Jack. And, because this is Violence Jack, he is molested because of this. MANY. TIMES.
When Kazuki of the Strings in Get Backers 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 realize that they've been attracted to Kazuki.
Major spoilers: 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 Yu-Gi-Oh! GX 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 Flame of Recca. 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 Fuuko, an enraged Tokiya shouts, "You idiot! I bet you thought I was a girl!"
Akira Shiraishi in Ai Ore! Love Me!, the 'princess' of his all-boys school, and considered a girl even by his brothers. Also dating the '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 ∀ Gundam 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 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 Writer Revolt against the execs not letting him have a female main character.
In Anatolia Story, Yuri mistakes a guy named Tito for her little sister Eimi. Funny, since Yuri herself is a Bifauxnen.
Husky the fishboy, from the manga +Anima, 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 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 attacks them in rage they don't realize he's a boy.
Souji Okita in Peacemaker Kurogane looks eerily like a woman. Other Shinsengumi members 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 YuYu Hakusho. 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.
Naru Taru's Norio "Nori-rin" Koga has very feminine looks and is often mistaken for a girl.
Rei in Fist of the North Star 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 Genesis Climber Mospeada 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 Vinland Saga 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 Gargoyle of the Yoshinagas. 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 They Are My Noble Masters. 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.
Envy from Fullmetal Alchemist, who is male in the first anime series 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 Zombie Powder. It didn't help that he's the leader of a gang called the "Ash Daughter Gang"...
Huey Laforet from 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 Princess Princess 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.
Black Lagoon: 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 taking off his shorts and showing Rock his genitalia.
Andromeda Shun from Saint Seiya 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 Morality Pet 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.
After Art Evolution, Katekyo Hitman Reborn! has suddenly started getting a bunch of them, including the protagonist. Chief offenders include Kikyo and Daisy of the 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 Baka to Test to Shoukanjuu. 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. Stupid Sexy Flanders ensues.
Shinji from Neon Genesis Evangelion is essentially a Gender Flip of Nadia (see here◊ for notes from Sadamoto himself). He was described by Sadamoto as looking like "a boyish young girl" (more evidence 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 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 crossdress Shinji for the role all while saying how beautiful "she" looks; Fuyutsuki's actions soon become overtly sexual.
The issue is not helped by Maya, who is essentially Shinji in a female officers uniform. And female, obviously.
Mumu Momoyama from 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 Sweet Polly Oliver once though.
Black Bird has Kyo, whom Misao mistakes for a pretty girl upon seeing him as an adult.
Ciel from Black Butler. Joker even had to ask if he was a boy to make sure.
Kenshin of Rurouni Kenshin, 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 Desire Climax looks just like his beautiful twin sister Mio Omori.
Frequently done in Kaori Yuki manga, not just in terms of art, but as part of the storyline.
In Count Cain, 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 Angel Sanctuary, 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.
In the manga, Ko Kijin wins a men-in-drag contest basically by showing up.
Yukinari from Girls Bravo. 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 grabbed his crotch.
Historical Japanese figure, Nasu no Yoichi, from Drifters is presented this way, to the extent that Toyohisa and Nobunaga both thought he was a girl at first.
Titus from Magi - Labyrinth of Magic 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 since he's an Opposite-Sex Clone of a female Magi.
Chibitalia (young North Italy). Many nations, including his caretaker Austria, were convinced he was a girl and the Holy Roman Empire even fell for him. Until Italy reaches puberty and his voice changes.
Poland already looks girlish, and then he talks in a schoolgirl dialect (translated to Valley Girl in English) and when he feels like it, crossdresses. When they were children, Prussia pointed out that Poland looks like a girl and because the Teutonic Knights had a vow of chastity, he had to touch his balls...Poland wasn't up to it.
A few characters in Uragiri wa Boku no Namae wo Shitteiru. Most notably Yuki who's even told he looks like a girl by other characters. Which is quite understandable as he has been a girl in all of his previous lives.
And in episode 14, Sodom, once he reveals his human form.
Daisuke Niwa from D.N.Angel. 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.
Shun in Here Is Greenwood. 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.
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 Captain Ersatz of 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.
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 Kunisaki Izumo No Jijou looks like a girl and is often mistaken as such. Because of that, he is also invariably assigned as an onnagatanote male actor playing female roles in the kabuki plays organised by his family's troupe, much to his chagrin.
Suriou from Kamisama Kiss. Some of the other characters even lampshade it when they remark that he is prettier than the female lead, Nanami.
Minoru in AKB49 - Renai Kinshi Jourei, 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 Boku Girl, 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 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 him popular with guys too.
Rintaro (narrating): Ruka: the embodiment of feminine grace and charm...also a total dude…"
Nagisa from Assassination Classroom 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 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 UQ Holder. 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 left ambiguous for some time whether Kuromaru is just a really feminine male or 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 No Biological Sex: 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.
Kanojo ga Flag o Oraretara: 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.
Waratte! Sotomura-san: 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.
Korbinian ("Bini") from Mingamanga is a Heavy Metal fan and has the hair. Also, the teacher mistakes "Korbinian" for "Korbinia".
In 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 snaps in response.
The Pokémon Send Your O Cs fanfic Pokemon Take Two 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.
Film — Animation
This is Francis the male ladybug's shtick in A Bug's Life. 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.
The '60s comedy What's New Pussycat? 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 Dark Shadows. 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). Fatty Arbuckle 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. 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 The Goon Show 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!"
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."
Sword Art Online due to the random generation of the avatar, Kirito, who already looks 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 Snow White!!!
Most males in the Anita Blake 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.
The Fool in Robin Hobb's works. 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 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 What Happened To Lani Garver. In fact, although the narrator finally just refers to Lani in the masculine form, the issue is never actually resolved.
Nakajima, protagonist of the Digital Devil Story series, is described as handsome in a feminine way. Specifically used as a taunt at one point.
Seregilunintentionally 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. Of course, later it turns out that the kid is bisexual and just hadn't realised it yet.
Vince Noir of The Mighty Boosh is mistaken for a woman (or more specifically, as his 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 Just Shoot Me!, though he is more often confused for being gay.
The CSI: Crime Scene Investigation 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 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.
An episode of Mad About You 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 Bishōnen 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, she's dead, 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.
Chappelle's Show: 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."
Noah's Arc: Even aside from the effeminate clothes, Romeo's physical features are remarkably feminine.
2 Broke Girls: Han remarks in one episode that a Camp Gay couple asked him if he was a "rice queen on the downlow"
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 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.
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 That '70s Show, Jackie uses makeup to glam up Kelso like David Bowie. 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!"
"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 "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 here◊
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 ''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.
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.
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 pretty◊ 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.
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 Miyavi◊, he looks girly even without make-up, skirts and hair.
It isn't just Miyavi who looks feminine even without trying. Shinya◊ from Dir En Grey has to be the best example of that. X Japan's 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 Mana◊, and that can distort perceptions a bit.
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 Robert Preston in Victor/Victoria, or Gene Hackman at the end of The Birdcage.
Michael Jackson spent some time between plastic surgeries looking exactly like his sister Latoya.
Ryan Ross◊ from Panic! at the Disco. 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 picture◊ where he must have been at least 19. He looks like the young girlfriend of the guy he's in the picture with.
Spencer Smith◊ (on the left). In his younger◊ days◊ he often looked girlish which was compounded by the fact that he sometimes wore girls'◊ clothing and jeans and usually stands with his hip cocked. You can see it in motion here◊. Now he still has a pretty face but usually covers it up with a beard◊ that's fuller at some times than others and a bigger, manly figure, also at times. He still ends up looking like a bearded◊ woman◊ sometimes though.
Everybody in the Japanese heavy metal band Dir En Grey used to look like females at the start of their career, especially because of the makeup.
The artist who painted the front cover of Daryl Hall And John Oates' self-titled 1975 album (the one with "Sara Smile" on it) make them look very effeminate◊ against the duo's will, especially Daryl, which would lead to stories that the duo were gay lovers. Daryl would joke in their 1998 VH-1 Behind The Music episode that on the cover he looked like "the woman I always wanted to go out with".
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, Mötley Crüe, Hanoi Rocks...the list is endless.
In Greek Mythology, 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 Nemesis for revenge.
In 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.
Raiden, from Metal Gear Solid 2. 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 Metal Gear Solid 3. 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.
Fire Emblem has a couple of these. The first one seen by Westerners was Lucius◊ from the seventh game, Blazing Sword. He's even mistaken to be a woman by Serra in-game.
Libra from Fire Emblem Awakening 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 Final Fantasy IX, 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 Viewer Gender Confusion page. Only once is this commented on in-story, when Queen Brahne calls him girly.
Zelos Wilder from Tales of Symphonia in spite of his masculine build. No doubt because of his long, wavy, red locks and wardrobe color of choice being pink.
Mithos is far worse as he looks almost like Colette. 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.
Flea of Chrono Trigger is mistaken for a woman when he first appears. Of course, that he is apparently 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 Eternal Eden fell in love with Jean despite Jean telling him that he's a man.
Ranmaru Mori of the Samurai Warriors series has a very feminine appearance, to the point that he gets mistaken for a woman in universe to the point of Running Gag status—he even "counts" as a lady for the purposes of Designated Girl Fights. Amusingly, one of his battlecries from Warriors Orochi is "I'm as dangerous as I am manly!"
As in other games, Pokémon Conquest 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.
Ace Attorney:: 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.
Parodied in Insecticomics when Moral Guardian 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 Flaky Pastry has an 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 Gold Coin Comics, Theo, whose job class (healer) is normally reserved for girls, is mistaken for a woman when Lance first meets him.
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".
Eutropia of Amazoness — it's actually a plot point.
Chovek, a minor character in Inhuman. The fact that he's pink doesn't help.
Lampshaded heavily and hilariously in Chasing the Sunset, 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 bishiness is pretty much par for the course.
Given the art style, pretty much everyone is of Ambiguous Gender 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 Vinci and Arty is often mistaken for being a female, at one point being mistaken for a pregnant woman in labor when pulled over by a cop. It Makes Sense in Context.
Unwinder's Tall Comics: 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!
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 Allen The Alien, who would't normally be this trope, is mistaken by the aliens for a girl; RR-TWTTW somehow think he resembles his daughter.
Axel from Demyx Time enjoys mocking Marluxia for this. Inverted when Demyx firmly believes that Larxene is a man.
In the Dissidia: Final Fantasymachinima "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 Whateley Universe, 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.
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 Distaff CounterpartSilver Breeze.
Gaia Online's Gino Gambino at one point looked very feminine despite the memetic "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 Art Evolution and an Important Haircut.
Home Movies - 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.
In an episode of Johnny Bravo, 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.
Seabreeze from the My Little Pony: Friendship Is Magic 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.
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...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 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.
Yoshiki Hayashi, again - because he has been confused offstage in pics at events unrelated to his band.
In a really truly depressing real life example, one of the victims of the real-life 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.
Somewhere between this and Cross-Dressing Voices: Haydn's Die Schöpfung (The Creation). The oratorio has three angelic soloists. Gabriel is played by a soprano.
The Venture Bros. 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 this news report on the "Teen Werewolves" phenomenon, especially their unofficial leader.
Persian Crown Prince 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 Ru Pauls Drag Race) looks and sounds like a lady even when out of drag.
The ancient Chinese strategist Zhang Liang was historically this. In Will of Heaven, it even becomes a plot point.
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.
Actor Daeg Faerch who is best known for his role as young Michael Myers in Halloween2007.
Noel Fielding looks androgynous at the best of times, and he can pull off a woman extremelyconvincingly◊ 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 The Mighty Boosh gets mistaken for a woman at least Once an Episode 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."