How do you roll up your sleeves? Of course it depends on the shirt and your measurements, but I neatly fold over the cuff, then roll it over two more times along the same lines. I unbutton any of the cuff buttons but keep the button that's located above the cuff closed. I suppose you can refer to this as the semi-buttoned triple-roll. The top of the rolled up cuff ends up about 2 inches below my elbow. Sometimes it hikes up over my elbow when I stretch, but I'm diligent about pushing it back down. Longer cuffs are a little tricky, and I avoid those shirts anyway, but I will usually fold the cuff in half, then roll it up twice. I'll call this the half-fold-triple-roll. What I really can't stand are shirts that have a different color fabric on the inside. I suppose if you like contrast cuffs, you may like contrast rolled up sleeves. I am a fan of neither. How do you roll up your sleeves? I've seen a lot of people do it in a very messy manner without any regard for the shape of the cuff. Some people button up after rolling. Some people even roll up French cuffs.