Rolling Method #1: The Casual Roll
The casual roll is the easiest and most intuitive way for rolling up your dress shirt sleeves. It is perfect for when you’re on-the-go as it is easy and can be achieved in seconds.
Just (1) unbutton the cuff and (2) turn it back once so that the inside of the cuff is facing out. Next, (3) using the cuff as a guide, fold it over once more and you are good to go.
The only problem with this roll is that it comes undone quite easily.