Let me state an instance which is familiar to me, which I think is an effective means to make the point (due to the still rather highly "taboo" nature of it in our today's society):- In Cosplaying culture (i.e. where people dresses up as their favourite Japanese Comic-book/Anime/VideoGame characters), females frequently dresses up as male characters and is accepted:- i.e. From a quick google... Females crossplaying as male characters of the popular Manga/Anime Naruto (that is a buddhist symbol, and not the Nazi sign btw) http://www.selectsmart.com/DISCUSS/file.php?33,file=134,filename=Naruto-Cosplay-2.jpg http://www.selectsmart.com/DISCUSS/file.php?33,file=131,filename=313302396_4292bc679c.jpg or perhaps some might be familiar of characters in the recent 3D Anime movie, Final Fantasy VII (Advent Children) crossplayed by 24 year old chinese cosplayer, MeiWai (美歪) http://www.selectsmart.com/DISCUSS/file.php?33,file=128,filename=yazoo1.jpg ...etc However, less frequently, when a guy crossplays as a female character, just for fun:- i.e. http://www.selectsmart.com/DISCUSS/file.php?33,file=133,filename=bearded_cosplay02.jpg =P It is frequently not even tolerated and people can get really nasty in response to it. Ok, kidding aside, there are actually some well-executed convincing male --> female crossplays too: This one's by a male cosplayer from Japan crossplaying a female character from the video-game KingOfFighters http://www.selectsmart.com/DISCUSS/file.php?33,file=124,filename=ash.jpg This one's by a famous 21 year old male cosplayer in China. http://www.selectsmart.com/DISCUSS/file.php?33,file=136,filename=1232pl.jpg Not sure of the rest, but they are all by guys too:- http://www.selectsmart.com/DISCUSS/file.php?33,file=125,filename=1846686wg.jpg http://www.selectsmart.com/DISCUSS/file.php?33,file=126,filename=CrossPlaying.jpg http://www.selectsmart.com/DISCUSS/file.php?33,file=137,filename=Crossplay4.jpg But even some of them are being called "gay" (with an offensive intent) or might even risk getting threatened when they are seen outside of their the "cosplaying convention" area, while the female --> male crossplayers were deemed acceptable. But a substantially "milder" (less "shock-value" perhaps) example would be that guys spotted wearing a "pink" coloured shirt, etc for instance would immediately be regarded as "gay" (in a bad way, meant to offend). Whereas females are not restricted to any colours that they wear. Then there's the movement against male skinny jeans, or metrosexualism, etc and there are a lot more instances that can be stated, and not to mention of the constant labelling of things by some people as "gay"; i.e. Idiots that go, "like oh my god, like that is so ~gay, oh my god!!!". I think all these examples illustrate the strong expectation existing for modern-males to conform to the hyper machismo mould (perhaps more so in places where there's a significant "western" influence", and are expected to strictly adhere to it. Frequently it is merely due to people resisting and fearing something that is "different" or do not currently fit in with what is currently perceive to be the "norm".' and fuelled by the current irrational cultural-taboo of the respective societies. Certain unjustifiable taboos (which differs from cultures to cultures, i.e. following from the first example, crossplaying for guys are quite acceptable in Japan/Taiwan/etc but not in the more Western-influenced Singapore) impose unnecessary conformity and restricts freedom for people to simply be who they are just so that they can "fit in" (i.e. guys frequently felt pressured to act tough and pretend to be "macho" and not able to freely show their emotions or fear). It limits self-expressions for one and induces frustration in those who do not conform to it. People in certain subsulture group, for instance, who go against taboos are occasionally condemned in an over-the-top way. For instance, the goth/emo scene, in western sub-culture etc were reacted upon a lot more negatively than some other less "taboo" subcultures like certain type of punkrockers, where violent fights frequently break out during the gigs and have real negativity impact to the society. It creates intolerance and discrimination to those who are "different" from the norm. and for no good apparent reasons other than for it simply being a deviation from the "status quo". At one point in time, women used to be restricted to wearing only skirts, sports used to be a man's thing, and many more. And there were no "good" reason to justify these "taboos" hence society gradually evolved. Thanks for the responses so far! And do feel free to cut and paste on forums to start similar topic to get people talking/discussing about this taboo issue. ;) I'm sure there are macho-heads who would even think that discussing this is "gay". I just did a quick google around and surprisingly, there are actually people promoting skirts for men! http://mensfashion.suite101.com/topiclist/article.cfm/skirts_for_men_new_fashion_trend And there were actually also numerous fashion leggings/tights/pantyhose made for men too. I've even read in an article that in Japan's street fashion, some of the more adventurous male teens actually dress up with really cool anime-inspired (or is it the other way round?) outfits with stripped leggings to match (aka the visual-kai style).