I actually witnessed a similar experience. When I was an undergraduate at Yale I was walking to the Chaplain's Office for my work-study job. As I was walking down High Street I saw a young african-american student walking in front of me. He was at the forefront of fashion because even over 10 years ago he was wearing his pants baggy. Just at that moment the bells on Harkness Tower began to chime the hour. The young man looked down at his watch to verify the time and he must have been late for class or something because he then took off at a sprint. However, his pants were so loose that he had to use his free hand (other hand holding books) to hold the front. And even then the rear of his pants slipped below the level of his butt and you could see the bottom of the guys boxer shorts!

All in all very silly looking then and still silly looking now. If you really must have that much freedom then just wear a kilt!