Conforming neither to tradition nor to modern taboos against overt misogyny, this guy's odd combination of feminine style and contempt for women puts him into an especially unusual position. Maybe some of his feminine traits might happen to have been a disadvantage to dating. Maybe he's just jealous that women wouldn't be considered as strange for similar mannerisms or lifestyles to his, perhaps wishing he were female instead as a result. Maybe he's insecure about his own lack of manliness, and seeing the traits he doesn't like in himself embodied in women brings out his inner resentment. Whatever the reason, he hates women while simultaneously acting in ways that are stereotypically associated with them.
Such characters will generally be villains (or at least generally more often than tomboyish girls who happen to have contempt for males, perhaps partly because women diverging from gender norms is relatively more embraced), and represent an intersection of Politically Incorrect Villain and Sissy Villain. However, some portrayals may nevertheless be more sympathetic, and make him an intersection of Noble Bigot and Real Men Wear Pink.
Can also be a deconstruction of Gay Best Friend, especially if that's a role he never asked for — maybe all those "hilariously catty" putdowns he's slinging around are more pointed that you thought they were. And does he maybe seem a bit overenthusiastic to make use of his honorary B-Word Privileges, or to detail exactly what he finds unappealing about women?
A Sister Trope of He-Man Woman Hater. Compare/contrast with Female Misogynist (as a subset of Boomerang Bigot), who have a similar issue, but the contradiction is more immediately obvious in that case, as opposed to an effeminate misogynistic guy who could instead have stereotypes about women that aren't the same as the gender stereotypes of the setting in which he's presented.
- Yurimaru from Ninja Scroll seems pretty contemptous of women. He is gay, but also very effeminate.
- The Lupin III franchise features several, usually cast as villains:
- The Pursuit of Harimao's Treasure has Herr Mafroditte, who was basically a narcissistic gay Nazi. When Fujiko touches him, he's visibly repulsed by it and tells her not to touch him because he hates women. Fujiko weaponizes this at the climax by kissing him on the lips, causing him to run away screaming in disgust.
- The Secret of Twilight Gemini introduces Sadachiyo 'the Scorpion', who's an effeminate Camp Gay assassin with long black hair, nail polish, and makeup. Lupin calls him names, like "that sissy assassin". Sadachiyo also has neither respect or patience for women, as seen in his treatment of Lara. And again when he confronts and, later, tortures Fujiko.
- And The Woman Called Fujiko Mine brings in the series-specific antagonist Lieutenant Oscar who looks and sounds like a woman, and hates Fujiko. He usually calls her "pig" or "spittoon". It is heavily suggested he hates her because of his secret love for Zenigata. She even got to sleep with him!
- Yuda from Fist of the North Star could count as a valid example: He's extremely effeminate and treats his harem as dolls.
- Deak Slathky from Black Cat is a woman-hating Serial Killer. He's also one of the most Bishōnen characters in the cast, to the point of Viewer Gender Confusion.
- Don't forget Creed, the Big Bad of the series. Granted, it's never stated that he hates all women but he has a grudge against almost every single recurring female character (and anyone who would dare get in-between him and Train).
- Jakotsu from InuYasha dresses like a woman, has a female voice actor on both sides of the Pacific, is Camp Gay, and is contemptuous of his female opponents.
- Akito from Fruits Basket comes across this way, until it is revealed that Akito is actually a woman. Her misogyny comes partly from her terrible relationship with her mother, who forced her into crossdressing merely because she was deathly jealous of Akito's father adoration for their daughter, and partly from her utter bitterness at not being allowed to live as her birth gender. After the very girlish Tohru helps her have a HeelFace Turn, Akito acknowledges how screwed up this was (and the consequences), and by the end she both wears more feminine clothes and is coming to terms with herself.
- The Villain Protagonist Serial Killer Light Yagami of Death Note repeatedly expresses his opinions on the uselessness of women, particularly his girlfriend Misa, who continues to ignore his rebuffing of her affections and the fact that he's using her to get away with murder. However, Light himself possesses a weirdly effeminate demeanor, with a special mention to the lovely pink butterfly belt he wears in the first opening sequence.
- Clair Leonelli from Heat Guy J is a more subtle example of this trope. He's a small, slender, physically-unimposing Bishōnen who also is in charge of the only organization in the series to contain absolutely no women, and he once disparages Daisuke for having to be saved by a woman on one occasion. note In the manga, he seems to ignore his girlfriend(?) a lot, except when he needs her expertise with robotics. On a more metatextual level, there's also the fact that his birthday coincides with Hinamatsuri, a festival associated with women and girls; but at the same time his own mother died giving birth to him.
- Most gay characters in From Hell. The book makes mention of the gay fraternity group known as "The Apostles" who occasionally show up in Jack the Ripper Conspiracy Theory lore, who were well known for their outspoken hatred of women (more than most people in the 1800s, even!). This plays into (and in the Apostles' case may have been an inspiration for) the British stereotype of homosexual men in general, especially in older works, that portrays them being very catty and mean to women, rather than the supportive "sassy gay friend" archetype more often seen in North American works.
- Freeza in Dragon Ball Insanity School is portrayed as one. As he stated, he "Hates every female life form, except for himself". He's also Camp Gay.
- Marik from Yu-Gi-Oh! The Abridged Series loudly proclaims himself the most effeminate guy around and generally disdains women, even believing that Yu-Gi-Oh! has no women.
- In A Charmed Life Light Yagami was brought up to believe that girls are weak and that showing emotion is a weakness. He's also rather fond of fashion, sewing, and home decorating.
- Light Yagami gets this treatment again in Those Who Stand for Nothing Fall for Anything, but also points this out in his friend-with-benefits Lawliet:
Light: He's surprisingly disparaging of the effeminate due to his hatred of women. I don't remind him of his decidedly camp music collection, but I blame his mother. He doesn't trust women. He doesn't trust men, either, or dogs, or cats, or bees, or horses, but he reserves a particularly spiteful hatred for women and femininity which I find as an equally cruel, unreasonable, and sexually attractive quality in him.
- Chi Fu from Mulan would be a milder example; he is a Non-Action Guy known for his Girly Scream, yet when told Mulan is a hero he simply says "She's a woman, she'll never be worth anything."
- Nekron, the Big Bad in Fire and Ice. When his mother kidnaps Princess Teegra (who is quite the Ms. Fanservice herself) to serve as his concubine, he is disgusted by the idea of mating with her, referring to Teegra as a "little slut" and throwing her in a dungeon. He does say that she is attractive for "a lesser beast" and he might take her after all, but this was said to goad her brother into attacking him. In fact, he shows more interest in the male hero than her.
- King Ard from Heavy Metal is a very effeminate man who hates women and considers them inferior to men.
- HIM, from We Are the Strange, is a pink guy who looks like he's wearing lipstick while smacking around a woman at his strip club and stating that women are "mere tools" of pleasure for him.
- Pavi Largo from Repo! The Genetic Opera is a woman-hating rapist, but he wears the face of a woman he killed and is generally effeminate.
- The Serial Killer Jame "Buffalo Bill" Gumb in both the film and novel of The Silence of the Lambs. It's carefully established that he isn't actually transgender, and that several gender reassignment centres have turned him away. Rather, he's obsessed with his dead mother and suffering from a vicious case of I Just Want to Be You. On the other hand, he's a large, gruff man who has to "put on" an effeminate guise, which doesn't come at all naturally to him.
- Lane, the teen who spearheads the cover-up of John killing his girlfriend in River's Edge, has a hint of this.
- Berdella, a film based on the serial killer of the same name, depicts its Villain Protagonist as this. It costs him his bazaar, as the property owner's wife eventually gets fed up with his attitude towards both her and other women.
- The Countess in book/movie Even Cowgirls Get the Blues.
- Buffalo Bill from The Silence of the Lambs; see Film above.
- Kay Brightmore from Doctrine of Labyrinths is a weepy gay soldier who clearly views women as naturally subordinate to men (as evidenced by his decision to arrange his unwilling sister's marriage) and repeatedly chides himself for "womanish" behavior.
- Notably averted by most of the gay and/or effeminate male characters in the story, such as Felix, Shannon, and Vincent, all of whom seem to value their female friends and colleagues and regard them as equals. It's pretty clear that Kay's misogyny is the product of his specific upbringing and cultural influences.
- Lestat of The Vampire Chronicles. Although he loves fancy clothes and fine surroundings, displays languid body language, and describes himself as a "mother" in making Claudia, he's "astonished" that a woman could have thoughts like Gabrielle's, underestimates Claudia's intellect and will, rapes a woman who tries to help him, describes women in general as "terrifying," and agrees with Memnoch that angels, despite being technically sexless, are "more male than female."
- Lionel Trane (a gay, activist teen) from United States of Tara was so misogynistic that he made other, more mature and secure gay characters uncomfortable.
- Jack from Will & Grace DID occasionally have elements of this (and Het Is Ew), but it varied from episode to episode due to Rule of Funny.
- The "hermaphrodite" Alpha Centauri in Doctor Who has a prissy, feminine personality and is voiced by a woman. Yet, in "The Monster of Peladon", he's very sexist towards Sarah Jane and the Queen (a trait he didn't display in his first appearance).
- Tom in Gimme, Gimme, Gimme often expresses misogynistic opinions. Then again, he does share a flat with Linda.
- Stargate SG-1: The System Lord Ba'al, who used to be an Evil Overlord, is a prime example of The Dandy, with his delicate features, often dressing himself in flowery robes or leather suits and concerned quite a bit with his own appearance. He also makes a bunch of misogynistic comments at Colonel Carter when he and SG-1 have been forced into an Enemy Mine, who punches him in the face in response.
- Sin With Sebastian in "Shut Up and Sleep with Me"
- Shooter Storm, whom New Jack claims is this way because Storm's mother only gave birth to half of him. Shooter Storm has an affinity for bright colors, an aversion to bruising and is out to destroy women's wrestling, one division at a time, demonstrated when he defeated Jillian Hall for the PWX Women's Championship belt and renamed it the United States title.
- Street Fighter II has Vega, a narcissistic effeminate matador who seemingly regards women with contempt and disdain. He wears purple eyeliner, nail polish, and what appears to be lip gloss. In the dubs, he tends to speak in a soft somewhat feminine tone. For years, gamers thought Vega gay, until Capcom clarified the matter by stating that Vega wasn't gay, but a narcissist. They even had him take an interest in Cammy's beauty, during the SF: Alpha series (so to speak), as a way of showing it.
- In Street Fighter II: The Animated Movie, he became jealous when Bison appeared to take an interest in Chun Li's "talents". And, when tasked with eliminating her, Vega's method was sadistic; delighting in Chun Li's suffering until she fought back and stepped on his face.
- Similarly, in the comics Vega gets pissed when Ken's fiancée Eliza, normally a Nice Girl, gets upset at him and gives him a hard slap to the face. If not for Ken being there, the poor girl would've been torn to shreds.
- By Street Fighter IV Vega seems to have settled for being less bloodthirsty towards women, in favor of passive-aggressive condescension. A good example is his rival intro with Chun-Li, whom he considers his equal in both skills and looks.
- Persona 4 presents Kanji's Shadow this way, a guy initially clad only in a fundoshi (who later transforms into a muscle-bound titan with a head of roses wielding Mars symbols as weapons) who speaks with an obvious "gay accent." He tells Kanji that he hates girls, because they always gossip and taunt him about his feminine interests, and then says he finds comfort in men. As the Shadow is supposed to be everything the individual hates about themselves, Kanji does not take this monologue kindly.
- Patrick Wells from The War Comms is an overblown parody of this trope, constantly whining about how all girls are "stupid" and "icky" despite taking pride in being so femmy himself.
- Omega Zell from Noob slips into this by being both Ambiguously Gay and a misogynist.
- Played with by The Nostalgia Critic. Vain, subby and girly, he's a feminist who nevertheless likes to occasionally poke female tempers so he can get dommed or at least slapped around.
- Camp Gay crossdresser Chris Crocker says he will KILL any woman he sees with a gay man. He says SHAVING is harder than giving birth. He claims he came out of his mom's vagina with his nose covered...