Pocket Square: Not Just An Afterthought After All

Dressing well is one sure way to enhance your personal brand projection. But donning a bespoke suit or jacket alone is merely the first of many steps to elevate your image. Let’s face it, most gentlemen who care enough about their personal brand would think like you too. And in a sea of gentlemen who’re suited and booted, how can you stand out? As the saying goes: the devil is in the detail. In this case, the icing on the cake can be as simple as an unassuming pocket square.

Close up of a woman (mother?) adjusting the pocket square in the breast pocket of a jacket (son?).
A pocket square is one of those optional extras that you can do without when donning a suit or tailored jacket. Yet, without one, you’re somehow incomplete.
Image by Wirestock of Freepik

Enhancing The Look Of A Properly Fitted Suit Or Jacket With A Pocket Square

We’ve already established that the quintessential garment of a well-dressed gentleman is his suit or jacket. But the suit or jacket is merely the foundation of a gentleman’s attire. Knowing how to build from this foundation separates the knowledgeable from the sheeple.

With a sound foundation, you can start to lay your support structure. In this case, your dress shoes, shirt, neckwear; and in the case of blazers or sport jackets, the trousers too. Whilst the neckwear is optional (though highly encouraged), the others are mandatory. Without your support structure, your foundation is incomplete. One simply doesn’t wear a jacket over bare skin, nor go barefooted.

Image of the Author being measured for a suit by a bespoke tailor.
Being measured for a bespoke suit is the ultimate entrance ticket into the world of the well-dressed. However, the suit is just the foundation for you to build the rest of your outfit.
Image by Jonathan Woo, courtesy of Solarex Imaging, an image of Leow Ho Keng of Sayap Bespoke measuring the Author

Once your foundation and support structure are in place, you can start adding on your accessories. And these optional extras are what make you stand out from a sea of suited gentlemen. Examples of these accessories are like tie clips, cufflinks, collar pins, wristwatches, and most importantly, a pocket square.

Wait A Minute… Isn’t A Pocket Square The Same As A Handkerchief?…

Historically, the pocket square and the modern handkerchief shared a common ancestor. The exact origin of the practice of carrying a piece of fabric on a person is unknown. But this trend boomed in the Middle Ages Europe. The upper class society carry a perfumed linen square on them every time they went out. It was a way to “protect” their delicate olfactory from nauseous smell as they traversed the streets. Before the days of central sewage piping, the poor urbanites discarded their waste directly onto the streets. And this resulted in The Great Stink of Central London in 1858.

A spread of five handkerchieves on a table, showcasing the limited patterns and colours when compared to pocket squares.
Modern handkerchiefs are made of cotton, and have a generally more mundane colour palette, or in most cases, solid white.
Image by Author

Made of delicate silk and intricately embroidered, the early handkerchiefs were status symbols of the upper class society. Whilst they served a utilitarian role, these delicate squares slowly transitioned to a decorative accessory for a well-dressed gentleman. By late 19th century, gentlemen began carrying two pieces of squares. The utilitarian square tucked in the trouser pocket, and the decorative square on the breast pocket for all to see.

“One For Blow, And One For Show”

The utilitarian square evolved into the modern day handkerchief. Usually made of hardy cotton or linen, they continue to serve the owner’s personal hygienic purposes. The “blow” in the abovesaid phrase indicates the action of blowing one’s nose in it. Hence, you launder your handkerchiefs regularly, same with your undergarments.

A man obviously suffering from some sort of flu, blowing his nose into a handkerchief, not a pocket square.
You will NOT be wearing that handkerchief as your pocket square. THAT one goes into your trouser pocket, out of sight from others around you.
Image by @wayhomestudio of Freepik

The decorative square that adorns the breast pocket took a different evolutionary pathway. From the quintessential white linen or cotton, modern pocket squares come in a variety of fabrics, colours and patterns. More often than not, silk is the fabric of choice for pocket squares. Silk is not only delicate to the touch, but also reflects light efficiently. Hence, printed silk is more vibrant looking than printed cotton or linen. The modern pocket square’s purpose is strictly decorative, hence the “show” in the phrase.

Incorporating Pocket Square Into Your Attire

Wearing a pocket square with your jacket, any jacket, shows a well put together outfit. A gentleman who sports a pocket square is one who pays attention to minute details. And if he can do that with his own outfit, he’ll do the same with his responsibilities too. That alone projects a positive personal brand identity.

Close up of the chest area, showcasing a textured royal blue jacket and white shirt. A patterned pocket square in a square fold peeking out from the breast pocket.
Enhancing the overall look with a splash of pattern on an otherwise mundane looking outfit. Note that the pocket square picks up the colours of both the blue in the jacket and the white in the shirt, harmonising the whole outfit.
Image by Hermes Rivera of Unsplash

Wearing a pocket square is as simple as propping it up so that it’s visible to everybody. But there are some “rules” on how to wear them too. Well, not “rules” per se, but guidelines to help create harmony in your overall outlook :-

  1. Never directly match your pocket square with your neckwear.
  2. Ensure sufficient contrast with the shell fabric of the jacket.
  3. Maintain the jacket-shirt-tie contrast for the pattern/colour.

So let’s take a look at some curated combinations to help you visualise them.

Formality Level #1 – Business Formal

For the times when dressing up means expressing respect, you’d want a look that subtly blends into the background. Solid charcoal or navy suit, solid white shirt, and a neutral solid colour tie is the rule of the day.

Close up of a conservative business formal attire as described in the caption.
Solid charcoal suit jacket, solid white shirt and solid navy tie is as formal as one can go. A solid white cotton pocket square in a conservative square fold will maintain the overall formality.
Image by Author

A conservative way to wear a pocket square is the rule of the day, no exception. Solid white cotton or linen, in a square fold, is about the most conservative way to wear it. The most amount of leeway is for the fabric to have some textured weave, nothing more. As long as it appears as solid white at an arm’s length, you’re good to go.

Formality Level #2 – Business Semi-Formal

You can start having some “fun” with your suit here. No longer limited to solid charcoal or navy, as long as you don’t go overboard with loud colours or patterns. You can start introducing subtle colours and/or patterns to your shirt too. Again, don’t go overboard with loud shirts. You can also start introducing colours and patterns to your tie too.

Close up of a semi-formal business formal attire as described in the caption.
Solid olive is a departure from the ultra conservative charcoal or navy suits. Paired with a contrast collared shirt in fine grey/blue stripes, and a regimental stripe tie to introduce more pattern into the mix. Take the opportunity to introduce a non-matching pocket square, but one that picks up all the colours of the tie.
Image by Author

You can’t match the pocket square directly to the tie, otherwise they’ll look too matchy-matchy. This projects a “lazily” put together outfit, an expression of thoughtlessness. However, you can wear one that picks up the colours of the tie and/or shirt. This will harmonise the whole outfit nicely.

Formality Level #3 – Business Informal

When you don’t need to wear a matching suit, a blazer combination obeys pretty much the same set of rules. You can, however, introduce more “fun” elements into your outfit.

Close-up of a blazer combo as described in the caption.
Solid navy blazer with brass buttons shows a deviation from the mundane “formal look”. Here it’s matched with a white shirt with pink stripes and a bright micro-patterned orange tie. The pocket square in orange base is to pick up the colour of the tie, but has a more elaborate paisley pattern.
Image by Author

A blazer combo allows you to have more fun when you don’t need to adhere to a formal dress code. So go ahead and introduce more patterns and loud colours to your highlights. As long as your base outfit is in neutral colours, you can go crazy with your ties and pocket squares.

Formality Level #4 – Business Casual

You’re not doing anything related to work, but still want to look put together, this is the outfit for you. Sport jackets come in a variety of textures, patterns and colours. The louder they are, the less formal they appear. And that goes for the accompanying shirts, trousers and neckwear too.

Close-up of a playful business casual attire as described in the caption.
Sport jacket in blue/grey glen check with red overchecks, this is the typical definition of a casual jacket. Here it’s paired with a blue/white herringbone shirt and a maroon knit tie with blue/white stripes. To further enhance the casualness of the overall theme, throw in a multi-coloured printed pocket square.
Image by Author

After office hours, or on weekends, but you still want to maintain a business appropriate look? Then business casual is the look for you. Playful enough for a drink at the bar, yet put together enough for an off-hour business meeting. In this situation, make sure your pocket square reflects your playful yet subtle expression. Pick up subtle colours from other parts of your attire, or go completely opposite with clash of colours. You can’t go wrong with either choice.

Formality Level #5 – Casual With Cravat

You’re out for a fun time in town, and yet still want to stand out from the crowd? Lose the tie and undo your shirt collar button. Then replace the stiff-neck looking tie with a pompous looking cravat. Nothing screams “fun” better than a cravat around your neck, and a glass of your favourite drink in your hand.

Close-up of a playful casual attire as described in the caption.
Unbleached linen sport jacket, light blue shirt with medium blue and pink stripes, and a bright maroon cravat against the neck. This is the typical summer holiday outfit at a members-only club. And don’t forget that bright red beacon-like pocket square too.
Image by Author

You want to stand out against an affluent and eloquent crowd, and yet not appear too stiff? Don’t just lose your tie. Instead, replace it with a less formal piece, a cravat. In a day and time when you see only cravats on the silver screen, you’re sure to steal the limelight. The brightly coloured cravat serves to call attention to yourself. Then choose a pocket square that harmonises with the cravat too. The last thing you’d want to do is to tone down your look with a bland looking pocket square.

Also Formality Level #5 – Casual With Roll-Neck

Sometimes, the casual ambience doesn’t justify wearing a tie. But exposing one’s neck may appear a little crude, especially when you’re with polite company. So instead of going with an open-collared shirt, consider a roll-neck jumper instead.

Close-up of a playful and casual attire as described in the caption.
Unbleached linen sport jacket matched with a fluorescent orange roll-neck jumper. Here, you can go with an equally loud fluorescent orange pocket square, or at least one that prominently features the colour in the mix.
Image by Author

In situations like these, the roll-neck jumper becomes the highlight of your otherwise muted outfit. So go crazy and put on one with loud colours. And pick up that same bright colours with your pocket square whilst you’re at it.

Formality Level #??? – Black Tie

All this time we’re only looking at business/casual events. But what about social events? What about glamorous events like black tie galas? How does one wear a pocket square with a dinner suit, and not stand out like a sore thumb?

Close-up of a classic black tie attire as described in the caption.
Dinner suit consisting of a black, shawl collar dinner jacket, pleated-front dress shirt with onyx studs, and of course, black bow tie. Black tie dress code isn’t the time for one to experiment with the outfit. So stick to the tried and true uniform of blacks and whites only. And that includes the pocket square too.
Image by Author

Black tie outfit is almost a uniform of sort. There’s very little room for one to differentiate one’s attire before it fails to meet the dress code. And you don’t want to give the ushers any excuse to refuse you entry to the party. So stick to the dress code. And that means solid white pocket squares…

How Many Pocket Squares Do You Really Need?

There’s no absolute number of pocket squares that one really needs. It all boils down to how many you can afford. Just keep in mind that you can change a look just by swapping your tie and/or pocket square. You can maintain the rest your suit/jacket combo and still look a little different. Plus, it’s a more economical way to achieve variations of one’s wardrobe.

A plan view of a variety of pocket squares on a table.
A small collection of pocket squares to match potentially any outfit.
Image by Author

However, if you’re just starting out, go with a white pocket square. Just like how a solid white is the universal shirt, solid white is also the universal pocket square. Once you have that, consider getting a combo pocket square with four different patterns on each quarter. And if you can survive all that, it’s time to go crazy and start your pocket square collection.

Are You A Pocket Square Fan, Or Are You Just Square?

Pocket squares have an almost magical way to enhance one’s brand image. It’s the difference between an elegantly dressed diner and the maître d’ of a fine dining restaurant. Do you have the mojo to pull off a pocket square? If you don’t, then reach out to Solarex Imaging to help curate a positive personal brand projection for you. And that includes how and where to buy garments and accessories that are not commonly available too. In the meantime, do let us know what stage of personal brand curation you’ve achieved. If your answer doesn’t fall neatly in any of the choices below, then drop a comment below the poll.

How many pocket squares do you currently have in your wardrobe?
13 votes · 13 answers

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About CHOW Wei Ming

Brand consultant, photographer, creative director, storyteller, and a true believer of the power of visual communications. Outwardly expresses a friendly disposition, but hides a perfectionist nature deep inside him.

6 Replies to “Pocket Square: Not Just An Afterthought After All”

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  6. A follow up to the article above, I was recommended a hardcover book called “52 Ways To Fold Your Pocket Square” by Trendhim. I knew there were numerous ways to fold pocket squares, but I didn’t know it was that many.

    You get a graphic of each finished look, a short description, and a visual step-by-step on how to fold it. It also comes with a folding difficulty rating for each style too. Indicated in number of stars out of five.

    One word of caution though, once you’ve seen it, you’ll be tempted to try them all. But if you’re interested to expand your sartorial expression with various styles of wearing your pocket squares, do consider giving this book a read.

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