Pocket Squares – Part 1: Embracing


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.


Winston Chesterfield is an amateur composer, fashion blogger, trained lawyer and style aficionado. He lives in Westminster, London and blogs at www.levraiwinston.com.


  1. It is something you get used to. I forgot to throw a square in my pocket one day last week and could not stop looking down at how incomplete I was. I nearly left the office for an hour to go home and retrieve one. It becomes the same as forgetting to wear your wristwatch. You simply feel “off.”

  2. I have been dying to get more pocket squares, but I can’t find a place with a nice assortment of colors, styles, and at a decent price. I don’t think the pocket square should be more than the shirt.

  3. Brian,

    Sam Hober offers good squares at great prices. http://www.samhober.com.