From what I can remember, tight-rolling hit the St. Petersburg, Fl area in about 1986, and remained a fashion trend until about 1990. Many have speculated just where the fad started. Below, I have demonstrated the steps in properly tight rolling your trousers. Some kids back in the day used safety pins to hold the rolls in place, but that was a definite amateur way to do it.
A properly tight-rolled pant leg would at least withstand the rigors of your first and second period classes before needing a refresh. I also notice that the Old Navy pants I am wearing in the pictures were not made for tight rolling. Levi’s 501 button-fly jeans, and Bugle Boy khakis. Some may also remember the Bugle Boy pants that revealed a little design on the underside of the pants, so when you tight-rolled them, you’d reveal a paisley pattern on the rollup. Start by pulling the cuff out completely. Next, fold over as far as possible without cutting off the circulation.
If you have “cankles,” tight rolling is not possible. Notice how the crease extends all the way up to the knee. This is important to achieve the proper “pegged” look. No respectable 80s kids wore socks!