Pocket Squares: Embracing and Wearing

For a number of years, I have adorned my jacket top-pockets. What began as a practice of sartorial experiments has evolved into a daily routine; I now adorn out of desire, no longer out of innocent curiosity.

My first experiment with the pocket square was an act of costuming and it was rather a failure; my perpetual fluffing and fidgeting attracted sympathetic glances but also squints of consternation. I was an amateur and my amateurishness was strongly indicated by my unhealthy and naïve action of ’correction’.

This was something I learned quickly and painfully. To wear a pocket square, one must not appear ill acquainted with the accessory. It should be worn as carefully, or as carelessly, as any other item. It should be treated with the same pride or naiveté.

To single it out for correction or fuss is to isolate it as an uncomfortable over-elaboration; and nothing is more fatal to the stylish boulevardier than obvious discomfort. To be uncomfortable in your clothing is for your clothing to be alien and such disingenuousness is mercilessly unflattering.

This is not to say that a chap should not experiment as his confidence grows; to try things on the street he has always tried in his bedroom mirror. It is perhaps ironic that we tire of relentless dress rehearsals and yearn for the unforgiving punches of the real world, but that is essentially what we want – the real opinion, the brutal honesty of wind, rain and daylight.

Our sartorial concoctions are made for the uncertainty of the world not the dust-filled comfort of our flattering and forgiving dressing quarters. If anything, there should be more experimentation, more of a dalliance with past sartorial glories, more people whispering ‘I’ve always wanted to try that…’, and so my cautionary words to pocket-square novices are merely that; cautionary. I offer such advice in the hope that others will avoid my embarrassing faux pas.

Adding colour or merely texture to the top pocket is a splendid way to smarten and sophisticate the ever-so-common two or three button jacket. At first, you will sneer into the mirror, perhaps expelling a guffaw or two, at how ridiculous you look but this is, I can assure you, merely a temporary feeling of awkwardness. Over time you will come to appreciate how well a pocket square finishes a look and how, possibly, it has changed your perspective on complementation, coordination and polish.

As a flourish, the pocket square is a reflection of personality. The more cautious men might opt for a folded triangle, just peering over the top of the breast pocket. Others might be outrageously adventurous and attempt the ‘waterfall’; beloved of eccentric artists and artistic eccentrics, this style is not so much peering over the top as, the name implies it, gushing from the pocket.

Your style of dress will dictate your pocket square fashion as will your mood, confidence and, yes, state of inebriation: I myself have dressed in such a state and have worn bizarre ’combinations’ of colours in my breast pocket that have given me the contrived appearance of a court jester.

I feel it is important to remember a pocket square as a flourish. The original purpose of such an accessory is not relevant here; no one will be handing these squares of silk and linen to perspiring dancers and today’s man would rarely adopt such a decorative item as a tissue due to the arrival of disposable Kleenex.

Types of flourish

Essentially, there are two basic methods of inserting the flourish; folding and crushing. There are literally tens of ways to fold and crush a simple handkerchief, and it would be imprudent to begin an exhaustive series on the subject, so this article will only attempt to offer guidance on the two methods and when to use them. Naturally, the creative amongst you will be tempted to elaborate on this guidance and this is to be encouraged. What is also to be encouraged is practice. ‘Pocket stuffing’ poses particular problems as incompletely stuffed pocket squares tend to drown in the breast pocket; some will only notice when they glance in a mirror that their ‘flourish’ has gone a-hiding.

Crushing and stuffing

These are my favoured methods of flourish. I like folding on occasion, but there is something spontaneous and more artistic about the ‘crush’. It must be noted that silk is more effective being used in this way; cotton and linen pocket squares lack that crisp sheen that highlights the irregular yet attractive undulation of material. The basic method is to take the handkerchief in the palm of your hand (picture step 1) and then keeping your fingers grip on the material invert it (picture step 2) and push the material into the pocket (picture step 3), making sure that the whole pocket is filled, push down gently (picture step 4). The finished article (picture step 5) can then be altered to personal taste. Some might prefer a tall and triangular flourish (picture step 6).


Folding is a more conservative method of flourish. Though there are many exciting ways to fold pocket squares, I intend to share with you a simple method that requires little time, practice or education. Start out by opening your pocket square completely (picture step 1). Now fold this square in half into a rectangle (picture step 2); fold again into a square (picture step 3). Fold this square into a smaller rectangle (picture step 4) and then fold roughly one third of the rectangle (picture step 5) and insert this into the top pocket. Make adjustments to the flourish (picture step 6) by separating the layers of the pocket square from each other to create a serrated edge (picture step 7).  For even greater simplicity, simply fold the material in half at step 4 and insert into the pocket (picture step 8).

The ‘waterfall’

As mentioned in the opening article on pocket squares and flourishes, the ‘waterfall’ is a very individual and rather rare method of adding flair. Some love it, many hate it – I remember a famous protagonist being Lord Sebastian Flyte, played by Anthony Andrews in the television production of Evelyn Waugh’s  Brideshead Revisited. The method is deceptively simple although you may need a safety pin or two to keep the thing from misbehaving; unsecured ’waterfalls’ have a tendency to fly off with the wind. Take the pocket square and pinch an amount of the material between your thumb and middle fingers (picture step 1); then push this part to the bottom of the pocket, leaving the rest unfolded (picture step 2). Make adjustments or secure the material to give your look the ’waterfall effect’ (picture step 3).

These methods of manufacturing a flourish are easily adopted into a daily routine because of their simplicity. I do admire the pressed pocket squares in Brioni catalogues and the intricacy of the formulated shapes but, pretty as they are, I have not been able to adopt them into my quick morning routine because of time constraints. There are many combinations to attempt, and if you have the time and patience, you can iron your silk or linen into precise shapes. If however you want quick ‘pocket flair’, the above methods are well recommended.