There's something happenin' here... what it is ain't exactly clear.
Let us take our time machine back to 1980-something. Say, 1987 if you just want to put a year on it. 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. I know this for a fact because I did it. 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?
Might as well jump straight off a building.
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, or tight rolled jeans, or pegging as it was called in various places, 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."
For reasons unknown, since I originally penned this article early on in the existence of When It Was Cool, it has became one of our most viewed and popular articles. I can not explain this phenomenon other than tight rolling (hot rolling, pegging, whatever) has apparently struck a pop culture cord. So, while you're here undoubtedly laughing with a friend about, "LOL remember when we used to do this in high school LOL" perhaps you'd also like to subscribe to our free When It Was Cool Podcast as well. I'm a lot funnier on audio than I am on paper and, like I said, it's free.