This has the makings of a very good discussion because the issue isn't black or white, but rather many shades of gray.
After a google search on the subject, most of what I find is related to other countries. I did find this article from all the way back in 2009. However, a lot has changed since 2009, so I don't know how accurate this still is:
http://www.nytimes.com/2009/11/08/fashi ... .html?_r=0
The article poses some interesting points, such as student safety and distractions. Bullying is a big problem in public schools, and a lone boy who may have already been a social outcast wearing a skirt could frankly get the crap kicked out of him over and over again. On the other hand, a boy who was in more of a popular circle, probably wouldn't want to wear a skirt in public for fear that it would isolate him from his other peers.
I believe most school age kids generally would prefer to stick with the status quo, as school can already be stressful enough as it is without striking out such a bold move of individuality. I believe that same holds true to young adults, and a good statistic is the age poll on this very website. Frankly, the older one gets, the less one seems to give a damn about what society thinks.
For the underage youth, societies view on him/her is everything. I myself wasn't enormously popular in school, and I can flat out say, that in my state of mind back then, there is no way I would have even considered wearing a skirt then. Believe me, I didn't need that kind of attention.
That being said, in a fun hypothetical situation, if I could take my current brain and put it back in that 16 year olds head, I would definitely give it a shot! (among other changes, to numerous to mention here) Granted, that would put us back in the late 90's, and politics were somewhat different then, but I'd do it, and defend my right to!
Which also raises another point. Judging from the discussions I've had with my own high school daughter, most youths are generally clueless about their rights. And to be fair, I am not to clear about them either, even at my current age. It is a proven fact that the constitution doesn't apply to minors (they can't vote after all). I've also been told, and have seen evidence that the primary custodian of all children in the U.S. rest with the state FIRST and the parents or legal guardian SECOND. As the schools represent the state, then they would have a big say in how students are to dress. But I'm not sure. Again, underage legalities are something I haven't really researched much, and are somewhat unclear to me. But I can back this up with some actual fact.... if you think the state doesn't have any say at all, send your child to school in rags a few times, and see how long it takes for child protective services to show up at your door.
I'd like to note that the point of the paragraph above was NOT to debate the legal guardianship of children, nor the role of the state or CPS, (which is a very lengthy debate not meant for this thread or website) but rather to point out some discussion points on how children would be allowed to dress in the public arena, and who sets the final "rules" on the matter.
As I don't have a son, I can not possibly test anything here in Damascus. The closest I can come is through Amber and her stories that she brings home. From what she tells me, there are a few homosexuals in her school, and she reports that they are generally "open" about it, and are not harassed as a result. She has often joked (maybe it wasn't a joke) that if I ever have to go to her school for whatever reason she wants me to go skirted. I'm not sure if that's a good idea or not. Even Amber may not be able to fully appreciate the bullying she may encounter as a result of such a move, at least that was my position back in August, however now she reports that pretty much everyone in her classes know about it now, and quite a few seem to approve, and I haven't heard of any protest at all. So we'll see. Schools are shaky ground for a 34 year old skirt wearing man. And I believe schools could be considered "public/private property", which tells me that they would most likely have legal ground to tell ME that I can not come to the school dressed like that.
I don't mind the community thinking I'm gay, but I really don't want the reputation of a pedophile.
Which brings me to Carl's response to the LGBT community. While again, there really isn't a lot of hard facts of actual students trying this to gauge a good hypothesis, I would certainly hope that like pelmut pointed out, they would come to the aid of any group that was falling under persecution. And considering that male skirt wearing, while not homosexual in and of itself, still is viewed by the ignorant as a "homosexual" thing, I do believe that the LGBT community DOES have a dog in that fight, and they would do well to support us. However that remains to be seen.
I personally take the position of freedom for all. That's why on issues I stand by the right to self expression. I even support the right to hate (non violently of course). While I don't agree with bigoted confederate flag waving conservatives, I'll stand with them in their fight to freely express their views, even if they cast stones at me for joining their protest with a skirt on. (what a slap of irony) We all get on a slippery slope when we start to say.... well this type of expression is okay, but not that kind. Then we have to ask ourselves "who are the moral police?"
Much like a lyric I heard off of one of my old 78RPM records I used to collect, it was a somewhat patriotic song of the late 40's that went something like "While I may not agree with you, I'll fight for your right to say it"... something like that. I can't remember who performed it.
Very good discussion, quite thought provoking.