I asked around about baggy pants, (specifically Sagging your pant to show off you boxers) And found out that sagging got started in prison so that when you did sagg it was to alert the other inmates that you we're a bottom (or open for anal sex)
as for me and baggy pants/clothes I dont really like it... If it doesn't flatter your body then you aren't dressed well... It doesn't nessisarily have to be tight all the way around I can't wear tight pants. with the way i'm shaped (the large cock don't help either) it looks odd I can wear fitted ones that have striaght lose legs and I will be fine...
My point is, everyone is different and should wear what look's good on them and what looks good to them.
as for baggy pants, I think that is a dying trend myself, i see lil skaters roaming aroung on their boards with pants i could never wear, and back in the day (1990's) it was cool for skaters to wear baggy jeans...