The pocket square is the canary in the menswear coal mine, announcing a man’s decision to view his clothes as an opportunity rather a necessity. Many writers have heralded the pocket square as the mark of a truly natty dresser - Bruce Boyer wrote that “a gentleman should wear a pocket square”; retired menswear doyen Will Boehlke used to say that most men should have half as many ties and twice as many pocket squares.
Budding dandies generally take eagerly to this sort of advice - I know I did. Pocket squares are fun to play with, offer a frisson of satisfaction at having the sophistication to wear this rare sine qua non of elegance, and what’s more, aren’t terribly expensive. Then there are the little thrills that come from women tugging at a pocket square thinking that it’s fake, only to unfold some medieval hunting scene or whimsical sketch of an Italian piazza. (This has happened to me exactly once. I have offered a pocket square to absorb champagne or tears - the two most commonly cited services a pocket square might do a gentlemen - exactly never.)
In this flurry of folded silk, it’s easy to forget the first rule of pocket squares: a white linen or cotton square always works.
Often the white square is presented as a disappointing last resort - if all your other squares clash hideously or match garishly with the rest of your outfit, give up and wear a white square. (And start shopping for a different square you can wear with this outfit next time.) Sometimes it’s even suggested that a white square is really only a good choice with conservative business suits.
As my initial pocket square fever has started to break (it took a few years), I’ve started to view a white square not as a last resort, but as a default. A white pocket square always looks pretty damn good. And it surely obeys Alan Flusser’s exhortation that the pocket square should “appear unstudied.”
The white pocket square sets a high bar that any alternative must clear to merit consideration. With a business suit, I wear little else. Even with sport coats, I wear a white square frequently - with the points up rather than in a TV fold, or with the fringes out in the nattily casual Post-Imperial version. I’m not the only one - it’s easy to find pictures of style icons like Cary Grant, the Duke of Windsor, and Gary Cooper wearing white pocket squares with sport coats and casual suits.
Of course, I still stuff a piazza or a fox hunt in my pocket now and again. But I no longer feel uncreative or unambitious when choosing a white square. Wearing a white square is not settling for mediocrity. It’s setting a high standard and holding to it.
Quality content, like quality clothing, ages well. This article first appeared on the No Man blog in August 2016.