I think it was Mad Men that did it, but around the mid-aughts a lot of men started wearing pocket handkerchiefs, or “pocket squares,” with their tailored jackets.  They’ve remained popular ever since.  Some men build up a collection of colorful silk squares that they coordinate with their ties, shirts, socks, etc.  So should you wear a pocket square and if so, what are the rules?

First of all, yes, you should wear a pocket square, because without one, the breast pocket of a jacket looks kind of naked – what’s it there for if not to hold a handkerchief? Also, wearing a pocket square shows you care about the details of your appearance.

BUT, you should only wear a crisp, white, 100% linen handkerchief.

Why is that? Because silk squares are colorful and shiny, and therefore by definition are flashy, which is a quality to be avoided in your appearance. Wear a silk square and you will invariably find that the eyes of the people you meet spend considerable time fixed on the square rather than your face, and therefore that the square distracts from what should be the center of attention – you, and whatever message you are trying to convey to another person. Also, silk squares are considered fussy and their wearers are often thought to be overly preoccupied with their appearance – i.e., vain.

You want people to think you care, but not too much – the message a man should convey with all choices in clothing and accessories. Hence the power of the white linen square: it’s not distracting, it matches with everything, and is appropriate in every setting. Your interlocutor may glance at it for a moment (thinking, here is a person who care about the details), but that’s it, and then it’s forgotten.

And how to wear it?

If you must fold it into a square, do so a little carelessly, and don’t iron it flat.

Better yet, grab it by all four points, fold it in half, and just stuff it in, points up (as an example, see this Ralph Lauren ad to the right). Don’t bother arranging it, and never get caught adjusting it in public.

Again, the square should be all linen, and should have hand rolled edges. Ralph Lauren makes a good linen square, but it’s a little large and bulges in the pocket, so even better (but pricier) are the half-size squares by Simonnot Godard of France (you can get them at Bergdorfs in NYC). You can launder your white squares just as you would a white shirt (Tide with Bleach, some Oxi powder, hot water, delicate cycle). Just like your white shirts, your squares should be kept lily-white and immaculate.

A final but not inconsiderable advantage of the white linen pocket handkerchief is that it can be gallantly whipped out to dry a lady’s tears (and never ask for it back). Try doing that with a silk square.

Instagram post.