Say no to monkey fists, crumpled mountain ranges, and jesters-in-hiding. A tortured or bombastic pocket square implies the same of the wearer.
For a silk square, this is what I consider ideal. It’s simple and organic, using the buoyant quality of good silk to its advantage rather than fighting against it. By bending the folds around a single curve, it holds the square in a lightly sprung, self-reinforcing shape. There is just enough tension to imbue it with life, but not so much as to make it appear clenched or awkwardly forced. Crucially, it is also easily repeatable and stays put during wear. This is as low fuss as it gets.
The technique is simple (click the image for a diagram). Start by tucking the square’s corners into your breast pocket. They should be deep enough so they won’t get loose. Then bend over the unstuffed end, from right to left. Push it in until only a single, rounded mound of concentric folds is peaking out. Adjust so neither too much silk nor too many folds are showing.
Wool and cashmere should be stuffed the same way. Linen, as always, should be folded.