Like many fashion crazes, I'm almost completely sure that this one began as a way to conceal illicit behavior. How could someone wearing pants that wide NOT be up to something totally shady? Also, I think my little sister has the dresser in the background.

Back when these pants were popular, in the second half of the 90s, 20/20 did a special report on Latino gangs in Southern California. Out there, the girls wore their pants so wide that they STAPLED them to their SHOES to prevent EXCESSIVE MOVEMENT. So innovative.

All you need to complete this outfit is an oversized polo shirt and a Nautica or Tommy Hilfiger boating jacket.

It doesn't matter if you've never set foot on a seafaring vessel, or that the jackets are not suitable for any temperatures below 50 degrees. Just focus on how awesome you look. Full disclosure: I owned the red one in 7th grade.