Whether a splash of flashy color, a sliver of crisp linen, or a puff of dusty ancient madder, there is no surer indicator of a man’s pleasure in dressing than the presence of a pocket square. Being fundamentally unnecessary renders them a bit defiant, bespeaking an aspiration to elegance above and beyond the call. There are few rules to wearing them, and fewer still that should never be broken, but like most men who’ve been recreationally dressing either too long or not long enough, I have my finely-grained and highly-held opinions on the subject.
First off, try to avoid calling them “pocket squares,” which makes them sound even more useless than they are. A good handkerchief should be relatively sheer, allowing it to be stuffed into a pocket without disturbing the smooth lay of the chest. (For the same reason, hanks don’t necessarily need to be as large as they generally are these days, particularly if being worn in a patch pocket. Vintage examples in smaller sizes abound.) Finely woven cotton or linen will crisp up nicely when starched and pressed, and fine silks will ripple more voluptuously. A good wool square, on the other hand, will tend to have a loose gauzy weave, affording texture without bulk. Hand-rolled edges are always lovely, but like most luxury touches, their absence shouldn’t be a dealbreaker; the goal is to look nice, not rich.
The next consideration is the context of one’s clothing, which is largely a matter of contrast. Black or midnight blue evening dress is best punctuated with white or cream. Coarse tweeds set off supple silks. Hard worsteds are enriched by soft wool. Large patterns against small. Complementary hues. Always present a harmonious whole; “popped” colors should only be worn very reluctantly when insisted upon by promising prom dates or inadvisedly young brides.
At this point, emphasis shifts from the hank itself to the manner in which it is worn. This is the domain of two related but distinct variables: personality and mood. The former by far the more important, ideally reflecting the wearer’s essential demeanor: think Don Draper’s taciturn TV fold, Astaire’s jaunty puff, Calloway’s exuberant blossom. Every man naturally falls somewhere along this spectrum. Be honest with yourself. Given the prominence of your handkerchief, it’s at least as important to choose its default presentation with the same enlightened vanity with which you select a collar shape or color scheme. Like those variables, it shouldn’t be a matter of ephemeral fashion, but your own attributes. You can pull it off.
Mood, of course, modulates personality. No man is precisely the same at both a board meeting and a nightclub, and an adjusted hank can reflect this more subtly than a loosened or lost tie. Such consciousness of presentation can get precious, but it’s often less a matter of expression than respect; in my first flush of youthful sartorialism, for instance, I wore a silk cream puff to my grandfather’s funeral, and have never quite forgiven myself.
When it comes to the actual stuffing, embrace a little chaos. Ignore all those illustrated pocket square origami guides which yield little throwing stars. Beyond an optional pass to smooth cotton or linen, the iron should play no role. Perfection is the enemy here; the breast pocket is the native environment for a dash of wabi-sabi, even with a straight fold. Go ahead and take your time to get it precisely wrong. It’s part of the fun, no one will know, and everyone does it.
A few specific tips to my personal taste? Fill the frame: use the full length of the pocket. Keep it simple: thinks leaves, not flowers. Having a bit of edge and a bit of puff tends to look more casual. Points should peek, not peak. Finally, when wearing a cotton or linen square, never miss an opportunity to use it; there is no more deliciously elegant gesture than plucking a hank to mop a brow, dry a tear, or uncork champagne. A genuinely nonchalant restuffing will always be perfect. Play it as it lies.
[Originally published in A Suitable Wardrobe.]