Well this is a little tricky...but I don't know any men that wear pants like that,... I have seen this thing and know it may be a style in some places ...but I don't know any man that understands man law that would approve of that fashion...what do I know...Im 46 and traditional
Yeah, I do think a lot of it has to do with age.
I work with a lot of guys under the age of 30 and nearly all of them wear that style... along with earrings and tats galore (as in entire sleeves--enough tattoos to completely cover their arms and make it look like they've been in prison) which I know can also be another generational (and regional) style.
And nope, I have to say that in this particular area of life, I was the total Good Girl. Never even tried to give a wedgie.
However, I can't say the thought has never entered my mind.