Enh, if you want the real answer to the transgender elements in recent male fashion...
Chicks dig it.
That's a generalization, of course, but there's a reasonable enough subset of the female population who appreciate either the 'confidence' or 'sensitivity' that sort of style exudes. Meanwhile, it lets those with an actual interest in pushing the boundaries blend in (a few surprisingly unrelated subgenres there), and acts as 'camo' for the truly reactionary sorts to be able to assert their masculinity and possibly have an excuse to beat the crap out of someone while still feeling attractive. "Everybody wins."
I think the amusing trend right now is "Steampunk" (secretly a warming over of certain aspects of '80s retro/'true goth' aspects, crossed with Clockwork Orange and Gibson fetishism) ... Watch out for monocles making a comeback.
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The whole baggy-pants thing took off for a number of reasons (rave fashion, appeal to awkward teens, cargo pockets for geeks/druggies, ease-of-shoplifting for some of the more urban types)... Dunno about the more absurd examples, but I'd say it beats Spandex on most people. ;-)
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Uniforms and dress codes can work to an extent (in terms of keeping everyone equally uncomfortable and disgruntled), but as someone who had his shoes stolen the first week at a dress-code enforcing school, they also increase the potential for malfeasance by imposing an irrational penalty.
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Oh yeah, and it sucks to go shopping for normal pants or shorts when you have a <=29" inseam. Apparently Americans aren't supposed to come shorter than 6', or I need to lose 50 more pounds.
