Tight rolling one's pants was a popular fad in the 1980's. Today, this form of wearing pants can be done to dress for a costume party or some other function.
Try to only use straight leg or tapered pants for tight rolling. Wider pants offer too much fabric for tight rolling and make it more difficult to roll. If using pants with wider legs is unavoidable, you may want to pin the pants after they are rolled in order to keep the tight roll secure.
Wear the pants. You cannot tight roll pants when you don't have them on. Don't try to do this before you put them on.
Pull one pants leg at a time to your side at the base of the pants and hold it securely. Be careful not to let the pants leg swing around your leg, and be sure to pull to the side and not upwards.
Place your opposite hand at the base of the pants, where the loose portion of the pants meets your leg. Be careful not to let the pants leg swing around your leg, or you will not be able to role the pants securely.
Fold the loose portion of the pants over the top of your opposite hand and the portion of the pants tightly encircled by the remaining base of the pants.
Carefully remove your opposite hand and keep the pants leg secure with the loose portion still securely folded.
Work your way down the tight pants leg to the very end of the pants so that both of your hands are holding the wrapped pants leg secure.
Roll the folded pants leg up twice, or as many times as desired.
Repeat the same steps for the second pants leg. It may take one or two tries before you have mastered making securely tight rolls.