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.

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Peter works in construction, but has an extensive collection of custom suits which he gets so that he can wear suits on the weekend. Even though he lives in San Francisco, he has never used the word "impact" as a verb. He writes about classic menswear and is one fedora away from being a complete dork.

5 thoughts on “How to Choose a Pocket Square

  1. Very elegantly put. At times it can be like pulling teeth to get guys to wear one. You forgot to mention wool/silk blends! Offers the feather weight of silk, but with a mattified finish and a little texture.

    • I agree Marcel – wool/silk blends are among my favorites, discussed at length in the pocket square thread in the forum. This is more a primer to demonstrate how to choose one in a suitable color & pattern.

  2. Please tell me who makes that tie that Pliny is wearing! I’m referring to the blue and brown one. I love it.
    Thank you!

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