ironic that hip-hop stars would still choose to wear ill-fitting clothes even after making millions of dollars and it's even more ironic that middle-class youths would adopt the unflattering style.
Another hypothesis put forth as to why baggy pants became so popular in the 90's posits that it is a way for boys and men to assert their heterosexuality and/or basically hide their sexuality. This assertion makes sense to me given that no woman I know, young, old or in-between, finds this look to be the least bit sexy. Instead of dressing to impress the ladies, these men are dressing to hide from their own gender. Sadly, they are hiding some of their best assets, literally, from those of us who would truly appreciate them!
An additional theory as to the origination of the barely there pant phenomenon goes back to hip hop's roots: in most prisons belts are forbidden to prevent them being used to inflict pain on others or to hang oneself. Prison clothes are also often ill fitting to begin with. While there are certainly a minority of women who like to date the bad boy set, the majority of us would like to know that our potential boyfriends have not been, nor are they going to go, to jail. So, again, this style of dress is in no way appealing to women.
The bare-your britches style is also unappealing to law makers. Proposals to ban baggy pants have started popping up across the country. For example, in one small Louisiana town, a $500.00 fine and six months in jail is imposed for those wearing pants low enough to show underwear or bare backside. Wow – that's low. (sorry for the awful pun)
Lastly, I have developed a theory of my own as to why so many young men seem to love the baggy jeans/ass hanging out style of dress: They want to look as different from their father, their teachers and "the man" as they possibly can. I just wish there was a more fashionably attractive and sexy way for them to achieve this goal.
Cher (played by Alicia Silverstone) in Clueless makes a similar side note about the guys in her high school sporting this look. With All the Young Dudes playing in the background she sums up this unfortunate 90's fashion fad as follows:
"So, OK. I don't want to be a traitor to my generation and all, but I don't get how guys dress today. I mean, c'mon, it looks like they just fell out of bed and put on some baggy pants, and take their greasy hair, Ew! And cover it up with a backwards cap and like, we're expected to swoon? I don't think so!" – Clueless
This 90's fashion fad really scraped the bottom (ok, I can't stop myself) of the fashion barrel.