How to Wear a Pocket Square:
Until recent years, the pocket square had all but vanished from sight. It took the unprecedented success of Mad Men and a broad cultural shift of men beginning to take a more active interest in their dress, to re-establish the pocket square into every day life in the workplace.
To me, pocket squares have always felt natural, a logical conclusion to getting dressed each day. They have a unique ability to sit quietly in the background (or loudly, depending on colours) and to help pull an outfit together completely.
On choosing the right one: When choosing a pocket square, many of the same guidelines which are applicable to picking out a tie, can be applied to here. Basic thinking suggests matching the colours of a pocket square to your tie, but this misses the point; that it should be worn in the more broad context of the overall outfit. Being well dressed is about an entire series of cloths, patterns and colours coming together to work effortlessly, not just finding 2 elements to complement each other. A pocket square can pick up the colour of a check in your suit, a primary or secondary colour in your shirt, as well as your tie. Developing an understanding for how a pocket square can work with various parts of an outfit becomes particularly relevant on days when a tie isn’t needed. This helps to ensure you won’t be left feeling uncertain about complementing other elements in your outfit, just because you don’t have a tie to match.
Texture and Colour:
Texture: As you would with a tie, match and complement textures throughout your outfit. If you’re wearing flannels, tweeds or more weighty wools in the colder months, as well as denims, these less refined surfaces are best matched with pocket squares in dusty silks, wools and cashmeres. In warmer months, brighter silks, cottons and linens will match the lighter weight and feel of many suits.
Colour: Unless you’re aiming for a simple white or pale blue square, or a white square with a coloured hem, look for pocket squares with more than just a couple of colours, as the addition of colour creates versatility. There’s a good reason that many of the world’s finest makers of pocket squares (Drakes, Rubinacci etc) choose elaborate patterns in their designs, frequently opting for paisleys. You only need a couple of complementary colours to be highlighted from your outfit and the rest of them (unless extreme) will fade into the background. It also adds versatility, as the addition of multiple colours in a pocket square allow it to be used with numerous outfits of different shades.
Complement, don’t match: There are a number of retailers selling ties with matching pocket squares. Avoid this option. It shows a lack of creativity and, again, gives an appearance of trying too hard to perfectly match your outfit.
How to wear it: If you take away only one point from this topic, it should be this: Aim to look as if you’ve just tucked it in your pocket before you’ve walked out the door for the day. Most men, if they wear a pocket square at all, opt for a straight (Hollywood) edge, with a neat line of cloth poking out above the top of the pocket, as was popular in the 50’s and 60’s. The look is too studied and sends a message that you’ve stood in front of the mirror, folding and adjusting it until it sat just right. It lacks the relaxed but attentive nonchalance critical in appearing well dressed and comfortable in your clothes. If you have your heart set on this approach, at least have it sitting casually out of alignment, or with the rear line of the square slightly above the front line. Imperfectly perfect.
Balance is always important, meaning it’s also best to avoid the peacock displays some choose, with most of the square seeming to have escaped the pocket and heading up towards the jackets shoulder. In most cases it comes across as a call for attention and tends to display insecurity in its wearer.
No right or wrong: Much has been written on the perfect way to fold a pocket square, how to achieve a triangular point, Hollywood line, fan effect and other arrangements. But it’s all too fussy and pre-meditated. Style should be fun. It should be relaxed. It should show that you care, but not too much. None of us are curing Cancer by dressing well and we shouldn’t behave as if we are. Have fun with pocket squares and fold them around, scrunch them a little, manoeuvre them in different ways, then stuff them in your pocket and see if it works, if not, pull it out and try again. No harm done.
You just want to find a balance which shows you gave thought to how you got dressed, but that you’re also not too fussed about trying to look perfect, either way.