When I was a kid, only poor people wore clothes that didn't fit properly. If you saw someone at school with their pant legs rolled up at the ends, it was clear they were forced to wear hand-me-downs from their older siblings. People who were sent into public dressed in such a manner were ridiculed and singled out for harassment. I know because I was one of those kids and I absolutely hated the punishment that the other children doled out on me.
We frequently get lots of student visitors to the lab that I work at. Several times per week the big yellow school buses from different middle schools and high schools in the surrounding area pull up out front and herds of children move past my office window on their way to our auditorium. Over the last several years I have seen plenty of examples of kids wearing their pants with the pant legs rolled up at the ends. From the way they were all dressed, it is clear that these were not old clothes that they were forced to wear. This was most certainly a style that somebody "cool" adopted and others took note and began copying it regardless of the existing stigma.
It would be interesting to go back in time, decade by decade, and have the school-age children prepare a drawing of what they considered cool. Looking at these paradigmic Rico Suaves as a function of time would reveal chosen styles that the next generation of kids would find downright embarrassing to be seen in. What is cool today will get you severely bullied tomorrow.