Rolling the sleeves above the elbow is usually reserved for when the work you are doing necessitates complete freedom of arm movement. A lot of guys keep their sleeves rolled below the elbow in every instance because they prefer the aesthetic of the sleeves rolled half way down the forearm and they would rather prioritize this aesthetic. Of course, I understand. I, however would like to submit a defense of rolling above the elbow.
Of course, sometimes rolling above the elbow is the best practical option. Sometimes the work you are doing necessitates this kind of a roll, and as someone who is passionate about using our clothes in functional ways, and not just as pure decoration, I support rolling the sleeves above the elbow on practical grounds when needed. As for the aesthetic element of this roll, I actually think there is something uniquely cool about this kind of a roll. Because it is almost always used when needed, this roll feels more utilitarian. There is something about it which feels as if the person cares less about the appearance, even if they obviously do care and did this roll intentionally.
Because, to many, it looks "worse" than rolling half way up the forearm, it takes on a more nonchalant and natural appearance. In this way it shares an element with a sprezzatura approach. It's strange because at one layer, rolling above the elbow appears more intentional as it is a more extreme shortening of the sleeve, but then at another layer, the layer where we operate as men who are interested in this style, it feels less intentional because it reads as prioritizing the aesthetic less than the functionality. How it is interpreted depends on who is viewing it. It's very interesting. I don't roll my sleeves like this every day, and not even 50% or 25% of the time, but there is a time when it is needed and a time when it even looks best. As with so many things, everything has it's time and place