Pocket Squares – Part 2: Wearing


In the introductory half of this double article, I imparted advice on how to take up the practice of adding a pocket square. This was vital as the second part of this ‘brace’ advances fairly swiftly, and quite without warning, into the practical side of adding a flourish. 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.


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. Nice observation.

  2. Michael, Austria says:

    I’m really delighted about your dedication to Pocket Squares.
    It’s nice to read articles from people who understand that the small accessoires make or break a look.

    Excellent read, keep it up!

  3. Blake, Troy, NY says:

    I was hoping part 2 would be along soon! Thanks. I always enjoy your posts.

  4. “Nice observation” was meant for other article. Don’t know how it ended here, but this article is great read too.

  5. Very interesting!!!