At studio 54 maybe
You wear whatever makes you happy dont worry about what others think.
Wear whatever is comfortable. Who cares what other think.
Sure, he can.
Should he? Not in public.
Boy or middle aged man? One should always dress age appropriate.
I think it depends on the body figure, the boy's character and whether it is the look they are going for but if all of those are fine then hell yeah! :D
Yes it would look nice on a nice slender boy!
on a guy, NO
Yes, certainly and many do