When I drop my teen-age daughter off at school I see a number of teen-age boys dressed in a similar manner. All fashionable in a Don't Ask/Don't Tell kind of way.
"Do girls like the way that looks?" I once asked her, honestly curious.
"It's gross, dad," she answered, rolling her eyes.
Every generation usually has its own style. From the zoot suits of the 40's to the polyester suits of the 70's. The 90's began with the grunge look, but that soon became the urban hippity-hop look, and that's where showing your derriere became popular. I've heard that this particular fashion choice had its origins in prison. In prison, you're either the one who wears his pants up, or you're the one who wears his pants down, and I'm sure it's no fun to be the one who wears his pants down. It gave the Don't Ask segment of the prison population easier access to the Don't Tell segment of the prison population, if you get my drift. Upon leaving prison the men who wore their pants down brought that look along with them, along with no marketable skills, where it was entusiastically adopted by urban males who thought it was a cool gangsta-outta-prison look. Sadly, it was more of a San Franciscan "treat" look. That look has stubbornly hung around more than ten years past what should have been its expiration date, and doesn't seem to be leaving us any time soon. Like I said, every generation has its own style. Except this one. This one's happy to be stuck in the 90's.
Years back I noticed teen girls walking around in public wearing boxer shorts or pajama bottoms. I thought it was a cute look, that is, until a few months back. I was getting an old-fashioned hair-cut at the Eastside Barber Shop, when in comes this grown man in his 30's wearing... pajama bottoms! I felt sorry for him. Obviously, he couldn't afford any mirrors. I've since seen other males, mostly teens, walking around in broad daylight wearing pajama bottoms.
I don't ask, and they don't tell.
Fifty Shades of Humor