Let's take our time machine back to 1980-something. I lived and loved the 1980's but I will be the first to admit we had some questionable fashion sense. For starters, everything was some weird shade of neon. Guys bought pump-up tennis shoes but left the shoe laces untied. Sometime around the mid-1980's, thanks to Van Halen, we went through a period where we tied a bandanna around virtually everything. We made pants, at one point, literally out of parachutes. Then we did the tight-roll. What the ever-lovin' hey was this all about?
You millennial knuckle heads have no right to laugh in your skinny jeans. They are just as ridiculous. In fact, we kind of came up with them first. The tight-roll was a simple concept. Let's pay for 32 inches of pants and roll them up to about 25.
I will argue that tight rolling pants did accomplish one objective. By rolling your pants legs up you could better show off your sweet L.A. Gear high tops. So maybe that's how that fad started. I've no idea.
Believe it or not, Wikipedia actually addresses the subject in their rather mildly titled "Cuff" article- "In the late 1980's and early 1990's, young people in some countries would tightly fold or roll the bottom of their pants. Reportedly, this "tight-rolled pants" or "pegged-pants" fad made a comeback in the 2010's beginning in London."