Be a square // Style Counsel

How-to wear a pocket square the right way

By Emir Aly Crowne

On Wednesday August 17th, 2011


photo by Kent WangAlong with fashionable ties or cuff links, pocket squares are one of the few ways a man can gentrify his business attire. A few years ago when I first started teaching, there was an impeccably dressed first year law student who — without fail — would wear a navy blazer, khaki pants and pocket square to class. He soon came to be known as Blazer, or Business Casual Mike.

Recognizing expertise when I see it, I have asked Mike (now an articling student at McLennan Ross LLP in Calgary) to share his insights.

A few simple matters should always be considered when wearing a pocket square:

While still a matter of debate, it is my view that a pocket square should complement your outfit. Note I did not say “match” your outfit. Some would argue that a loud colour or design is a piece unto itself and need not account for the rest of the ensemble. I disagree. Your pocket square should be coordinated with your tie and shirt. For example, I am fond of a purple square to accent a mauve tie and to bring out the light purple strip in my shirt. These three need not match; rather they should bring out the best in each, creating a polished look that draws the eye from one to the other.

The key in selecting a fold is to give the appearance of effortless style. Choose a style that suits you. The classic clean edge (think Don Draper) is always good. Alternatively, any number of complicated folds (four corners up, two peaks, the trio etc.) will clearly set you apart. For those in a hurry I would recommend This St. Louis–based company will create pre-folded pocket squares, which can simply be inserted into your suit jacket, for under $10. Of course, the simple “poof” is always acceptable as the epitome of effortless style in a pinch.

Rules of Use
The old rules of style dictated that a gentleman would always carry two pocket squares; one for use and one for show. I leave this point to your discretion. Also, it was common to have your initials stitched into the square and to then display the lettering outwardly. I am of the opinion that initials are best left for cuffs and not pocket squares.

Michael C. Barbero is a Student-at-Law in McLennan Ross’ Calgary office. Emir Aly Crowne is a Law Professor at the University of Windsor, Faculty of Law.  Both are sometimes square, though never obtuse.

Photo by Kent Wang