Updated: Jan 25, 2019
Gentlemen, ask any woman you know and she will tell you there is something undeniable attractive about a man who rolls his sleeves up. Now, bad examples of this run rampant. For example, the high school roll. If this isn't already a term, mark you calendars and edit your dictionaries because I just made it a term. The high school roll is an instant outfit killer that screams amateur, this roll is a broad cuff roll that exposes one's elbow.
Gentleman, for the love of all that is holy... never go full elbow.
Instead, understand there are many types of rolls that each have their own advantages. For example, in a causal outfit with a flowy linen shirt a messy double cuffed roll will exude a laid-back and relaxed vibe. Alternatively, perhaps the cocktail bar on a summer evening is a little too warm for even the butterfly lined blazer you're rocking. Let your date watch you gracefully remove the blazer and roll a tidy double cuff, just enough to show off the watch that's been peaking out all evening and a fit forearm. For dress shirts make sure you never fold the cuff of the shirt over itself, this will make for neat and wide rolls. For casual shirts this rule does not apply, and often the messier and asymmetric the rolls, the better the end result.
There is something about the forearm and the act of rolling ones sleeves that exudes confidence and communicates style to women, but don't take it from me go find out for yourselves!