The 4 Best Ways to Wear a Pocket Square

Almost six months ago, I wrote How to Choose a Pocket Square, showcasing some of Styleforum’s member’s pochettes and how they used them to accessorize various coat and tie combinations.  Still, much like a child eagerly pores over paint brushes when first handed one, many have little to no clue what to do with them, and so impulsively stuff a blob of fabric into their pocket without regard to proper technique.  Granted, it’s not rocket science, but like all other components of classic men’s clothing, a bit of know-how can make a big difference. 
First, should you wear a pocket square?  Forum member Will, creator and writer of A Suitable Wardrobe, recommends a square for all empty breast pockets.  While that may have been appropriate when coats were worn with only trousers, nowadays sport coats can be seen with jeans and even sneakers.  Should you wear a pocket square in this instance?  Since a pocket square dresses up an outfit, whether or not you choose one depends on the look you’re going for.  Are you sporting sneakers and beat-up jeans with that sport coat?  Then skip the square; it’ll look out of place with the casual kicks, like a top hat with pajamas.  A pocket square in a sport coat with raw denim and loafers or wingtips, however, give off a similar dressier vibe.
How should you wear your square?  As with neckties, simpler is better.  Countless YouTube videos demonstrate a dozen ways to fold and place pocket squares in increasingly-complex methods, most of which are fastidiously abominable.  The following are not only the best ways to wear a pocket square, they are the only ways you need to know.
The Square Fold (AKA the TV Fold, AKA the Presidential Fold)
The most basic fold, often seen in Styleforum’s “Conservative Business Dress” thread.  Anesthetized and inoffensive, this option may be perfect for the rest of your outfit if you are going to a formal event or if you work in a conservative office (think grey worsted suits with black captoes).  However, many people make the mistake of folding the square so that none of the seams show, and are instead left with a perfect, paper crease-like fold at the top of their pocket.
This is a proper way to do it: place the square in your pocket so that the edges of the square are facing the shoulder and arm.  This gives a touch of visual interest to an otherwise, well, boring square.  Try angling the outside corner up and out toward your deltoid.  This way the diagonal lines of the square’s edges echo the same contours of the V of your suit and lapels.  For extra credit, space the edges apart haphazardly as you fold to create a more organic square-ish fold.  This type of fold works well with small repeating patterns, and of course, plain white linen or cotton.
The Three Point Fold
Variations of this one exist (Two and Four Points), but even numbers seem to make an already artificially manipulated piece of frivolous cloth overly contrived.  To do it, simply fold the square in half on the diagonal, bring the left corner up over the top so it falls on the right, and then the right corner behind so it falls on the left.  A less studied look than the Square Fold, and works with all squares.
The Puff
The puff is basically a half circle, accomplished in several ways.  The easiest way is by simply shoving the points down in your pocket, leaving a puff at the top.  This can sometimes look a little shapeless, so another way is by pinching the middle of the square, twisting it, and folding it.  This creates soft pleats that give the square an interesting dimensionality.  Another way similar to the last is after pinching the square, bringing it through an O of your thumb and forefinger, and then folding it in half so that the points are either behind or on the outside edge of the puff.  Best for abstracts, paisleys, and large prints.
The Whatever
Another option is to do combinations of the three above. I find myself doing the Three Point and Puff Fold regularly. I also like how Will at A Suitable Wardrobe puts it: shove it in, direct points toward your left, and forget about it.  This is basically what is demonstrated by TTO here:
Pocket squares, like most articles of menswear, follow simple rules of aesthetics and harmony.  You may not always need one, but when you do, practicing these tried-and-true methods can make your pocket square an elegant accompaniment to your ensemble. Finally, for your edification and viewing enjoyment, I’ve put together a video, which you can watch below:

How to Choose a Pocket Square

Are you a pro-pocket square person? Perhaps you’ve heard that they are the cheapest way to “upgrade” your wardrobe, but you’re hesitant. You feel safe in your white shirt, navy suit, and black shoes, and while you’ve seen them on other guys, and even liked one or two, you could never see yourself wearing one. Maybe it’s because you don’t want to call attention to yourself. You’re wary of getting into uncertain territory, and after all, a pocket square serves no real practical purpose.

On the other hand, you may have completely lost your mind and gone square crazy, spending as much on them as you would for a well-made suit. You’ve bought untold folds of squares in every color of the rainbow. You even have a division of solids, designs and patterns, cottons and linens, woolen and silk. And why not? Most are dirt cheap, even if you splurge on one, you won’t be dropping much more than a Benjamin.

Let’s assume for a moment that you are a balanced individual that enjoys classic menswear and wishes to appear like someone who cares, but not fastidiously so. You’ve seen pictures of old Hollywood stars or various gentlemen throughout the past 100 years and admired how some of them can pull off the pochette. You’ve considered getting one; you may even have a few. How do you wear it without looking like you’ve consulted an article – like this one?
Many how-to’s have been written; often peppered with precision diagrams, architectural blueprints, and earnest cries to wear a pocket square in order to defend the dapper man’s heritage. This is not one of those articles. In fact, it should be said that it is better to wear no pocket square at all than to wear an ill-chosen one, and let’s face it: most pocket squares are hideous. Rather, we’ll showcase some of how some of Styleforum’s own members wear them, and learn from their example.

Our first member to showcase is @Pliny. I’ve always liked how his outfits combine differing scales of pattern, even though I maintain he takes horrible pictures of his successes. Let’s look at a few examples.

When wearing a small-scale gunclub jacket, a pocket square with a large design keeps things from looking too busy. Notice how the mostly cream color of the two complement the jacket, shirt, and tie in both ensembles. These are perfect examples of how well these types of pocket squares work with practically any combination of coat and tie, including, as Pliny demonstrates above, a solid grey suit.


Next up we have @TTO, of whom I wish the forum saw more. His creative nod to vintage style may not be to everyone’s taste, but it is always refreshing.

One of the regular pitfalls of the pocket square is wearing one that doesn’t contrast enough with the jacket you’ve chosen. TTO wisely opts for bold white stripes to set his square apart and still echo the light shade of his blue shirt.

Finally, we have Mr. Six, who always has a small sliver of good taste stuffed into his breast pocket. Although not always in solid suits, these two pictures showcase how even in a conservative environment one can enjoy pocket squares without resorting to absurd designs or obnoxious colors.



In both pictures, Mr.Six has chosen a square that contrasts with his jacket, either lighter or darker. Far from standing out, the luminance of the pocket square in the first photo harmonizes well with the shirt, and the dark colors of the pocket square in the second echo his tie.

Pocket squares, more than most other items in a man’s wardrobe, are difficult to wear well. The ideal pocket square choice neither adds nor takes away from an ensemble, and is instead a harmonious but not attention-grabbing element of the outfit. Far from being detrimental, such choices are in fact a good thing. The components of an outfit should look as though the wearer carelessly threw them together in such a way that nothing matches but everything complements; neither too studied nor too heterogenous. Admittedly, this is more of an art than science, but there are a few guidelines that can help you chose a pocket square that at the very least jives with the rest of your outfit, if not a slam dunk:

  • Silk is always a correct choice, but shun overly shiny squares. You don’t want iridescence to blind onlookers and take their eyes away from your gleaming smile.
  • Solid-colored silk squares are bad, except perhaps in cream. White linen or cotton is far better, and is by far the most versatile pocket square you can own. Really, if a plain white linen or cotton pocket square won’t work, you’re better off with no square at all.
  • Try to contrast the square with the color and brightness of your jacket, as well as with the scale of the patterns in your outfit.
  • Avoid pocket squares with the same pattern as your tie to keep from looking too calculated.
  • Don’t succumb to the interweb’s love of the pocket square explosion. That’s just a stylist’s way of quickly stuffing the fabric into a mannequin’s breast pocket. Keep the puff politely subdued and prevent your points from peacocking.

These above pictures are just a handful of the many good examples of pocket squares you can find on the forum. There’s an entire thread devoted to them, and many users are happy to go into even further depth, including seasonality and fabric choice. The perfect pochette can subtly enliven and enrich your ensemble, but choose unwisely and you may look overly affected and foppish.

Really, at the end of the day, it’s just a useless piece of fabric, and if no one noticed your square, you have claimed a victory.