Rule 7: Wear a white linen handkerchief with your suit
Of all the colours and materials available for a pocket handkerchief, white linen is considered the smartest and most formal. Why? Well it's a question of two factors - complement and contrast.
A silk tie is definitely smarter than a wool or linen one. The shiny lustre of the silk and the way it contrasts with the rougher texture of the suit creates a pleasing distinction. So why isn't the same true for handkerchiefs? Why isn't silk smarter than linen?
Because the contrast between silk and wool has already been achieved with the tie. More silk would be too much. Instead, the white linen echoes the sharpness and matte texture of the suit - it complements it.
This is also the reason that a wool handkerchief would be too casual. Yes, it is matte and rough in texture like the suit, but it is not sharp like the suit. It only shares some of the characteristics.
So this is the rule. Or rather, this the reason that men of taste over the ages have most often worn a white linen handkerchief with their wool suit and silk tie. Why it has become convention. Complement and contrast.
So how to break the rule? Well, many men don't wear a tie every day. If you don't, there's no silk to contrast with your suit - which is a pity. So wear a coloured silk handkerchief instead of a linen one when you are tie-less. This is my rule of thumb most of the time, though I will also wear linen when I feel smarter.
Another way that the rule is broken: tweed jackets. Men of style will often say they like silk handkerchiefs with their tweed jackets because of the contrast in texture. But they weren't saying that about their suit were they? Then it was all about complementing. One reason may be that woollen or casual ties are often worn with tweed. Another may be that the sheer roughness of tweed needs greater silk to balance it. Certainly, a silk handkerchief is often worn when tie-less with tweed.
Having understood why the rule, or convention, is there, it is easy to find creative ways to make use of its wisdom without necessarily following it.
In this case, be aware that all decisions with accessories are about complement and contrast. That is why a white silk handkerchief with a tie always looks a little effete. And it is a good argument for wearing woollen ties or handkerchiefs with modern, shiny worsteds. Just not both, probably.
Yours truly has recently teamed up with "˜A Tailored Suit' to bring to you a special Q&A segment about men's style. This segment will attempt to tackle questions about fundamental men's style. It is also a great opportunity for you all to chime in on to add your two cents. Please post questions you would like for us to answer.
Are Pocket Squares practical? Can you wear one to work, or are they best reserved for more formal occasions. What do you see on the streets of New York?
A Tailored Suit
The short answer is Yes, pocket squares are practical and should be worn with a suit, odd jacket, and even overcoat if the weather permits. But what purpose does the breast pocket serve; why is it even there if not to fill it? Whenever we see a man without a pocket square, it immediately signals that he is either unaware of the strengths this small flash of color can impart or he does not possess the confidence to be different. Because let's face it, more than 90% of men do not wear a pocket square. To display a handkerchief on your chest is to clearly announce you do care about appearances.
With that being said, always pay attention to your environment and adapt if necessary. If you are going into an interview at a conservative New York law firm, perhaps this is the moment you do conform and keep the square tucked away. If you do decide to wear one, go with a simple white cotton or linen and choose a simple fold such as the square fold. Save your bright paisley handkerchief and puff fold for when you land the job or when applying to Esquire.
You also need to be confident in wearing a pocket square - hence this is the best reason to place a handkerchief in your jacket breast pocket as often as you can. Nothing breeds confidence like familiarity and you want to get used to it being there. Once it becomes normal to you, you'll wear it effortlessly. And that's when it will help you look your best.
Finally, remember that a pocket square is only an accessory. Like a spice in a finely prepared dish, it should add to the whole but never overpower it. If your bright handkerchief is drawing more compliments than your keen insight, you may have a problem.