There are many ways to wear a pocket square, but only one rule – always complement; never match. As with tie knots, card tricks, and pick-up lines, you want to look good without seeming like you put in too much effort. Any hint of contrivance and the magic is gone. For pocket squares, that means looking like you grabbed something at random (n.b.: use caution in applying this logic to pick-up lines) and things just happened to work out perfectly.
The Elysium of nonchalant perfection is bordered by hellscapes of priggish foppery and slovenly carelessness. These borders are poorly defined and to some degree a matter of taste. However, here are some good guiding principles to keep you on the right side of enemy lines:
Color: The trickiest part of wearing a pocket square is knowing how to combine colors. Just as you should never buy matching tie and pocket square sets (let alone wear one), you also never want your tie and square to match too closely. Instead, choose a square that either picks up a secondary color in your tie or complements the main color. For instance, suppose you’re wearing a tie that’s navy with burgundy pencil stripes. You could wear a burgundy square to highlight the burgundy pencil stripes in your tie, or a dark brown square to complement the navy base color.
Pattern: Squares with big patterns often look best with neckties with small patterns, and vice versa. Doing so keeps either accessory from competing with each other. Squares with “motif” patterns - that is, an unrepeated sketch that takes up the entire square - work with any tie pattern.
Material: A clean, sharply folded white linen will look good with almost anything, but day-in-day-out white linen pocket squares can get a bit boring. Consider mixing things up with silks, wools, and cottons. The first is good for year-round wear, while the latter two are a bit seasonal (wool for fall, cotton for spring).
Sheen: Pay attention to how light reflects off the material, and use it to balance the rest of your outfit. A wool square can be a nice seasonal accent to your usual navy sport coat and silk tie combo, whereas a silk square can keep a tweed jacket and wool tie ensemble from looking too fuzzy.
Fold: Don’t over think it – this shouldn’t feel like origami. Neatly fold linen squares and slide them into your breast pocket. For anything else, pick the square up by the center, fold it over so that the center is touching the square’s edge, and then stuff it into your pocket. Points up or down, it’s up to you, although points down will always look more discrete.
Done right, a pocket square can elevate the look a tailored jacket – decorating the breast pocket, balancing the tie, or adding visual interest when you’re going sans neckwear. It’s arguably the easiest accessory to wear, or at least you should make it look that way.
Quality content, like quality clothing, ages well. This article first appeared on the No Man blog in March 2016.