A Gentleman's Guide to Rolling Cuffs:
You know who you are, you brigands. You men who have taken the no-break, Thom Browne aesthetic to its breaking point. You men who saw a photo of people sockless in monkstraps at Pitti Uomo and thought that was a perfect way to spend every waking hour. You've been rolling up cuffs so large, with trouser legs so short as a result, that you might well be wearing capri pants. To which we say: enough. This madness must stop. That is not to say there is anything wrong with cuff-rolling as such. It can be a charming aesthetic when done properly, bringing a carefree quality, a roguish quality, to a casual wardrobe. But like so many other aspects of fashion, if done too much it can lead to disaster. Moderation is the name of the game here, like in so many other trends.
Herewith, we share a few general guidelines about rolling up one's cuffs, both for pants and for shirts.
First, when it comes to pants, remember that there is a time and a place and an occasion for cuff-rolling. No one wants to see your bare ankles in December, or when you're in suit and tie at a board meeting. Rolling one's cuffs is an inherently casual act, and therefore should only be undertaken when the circumstances are casual: weekends, days off, vacations, and the like. Know the occasion for a cuff roll and you'll be halfway there.
Second, remember to not take it too far. Your pants shouldn't be hiked halfway up your calves. The objective isn't to turn your trousers into shorts, but to show just that hint ankle to let others know that you are truly relaxed. Two turns of the pant leg are sufficient, and sometimes only one will be enough.
Moving on to shirts, the same rule applies to pants: don't roll your shirt sleeves up too far. Again, the idea is not to emulate a short-sleeve shirt, but rather to peel back some of the formality inherent with a long-sleeve shirt, to tone down the stiffness that rules in the office. To the elbow is probably the limit of the shirt sleeve roll, and mid-forearm is the Platonic ideal. Finally, when it comes to shirt sleeves, pick a rolling style and stick with it. There are two generally agreed upon methods. First is to simply roll over the cuff and keep rolling until the sleeves reach the desired height. The second is to pull back the sleeves all the way to the desired length, then roll up the pulled-back sleeves, leaving the cuffs to peek out from the roll. The latter is usually preferred by politicians, the former by more working-class backgrounds, but both are acceptable. Just don't use a different method for each sleeve, and generally, don't switch between them too often. The whole point of rolling both pant legs and shirt sleeves is to project a laid-back, casual air. The idea is to look like you're not trying at all.