How to Wear a Pocket Square (Like a Boss)

Dave Bowden

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Blue suit, black tie and pocket square

You’ve probably noticed that when you’re awash in a sea of suit jackets and blazers – think weddings and more formal office settings – accessories like pocket squares can give your look an extra dash of dapperness that helps you stand out from the sartorial crowd.

The problem is that while the pocket square seems easy enough, most guys fail to master it.

At least, I certainly did. At one point in my early 20s, I’m embarrassed to admit that I actually folded some Kleenex around a square piece of cardboard in a desperate (and very, very sad) attempt to re-create the crisp white pocket squares I saw on Mad Men.

It was… not great.

Not great bob gif

Fortunately, I realized that tissues weren’t the answer, and finally invested some time into researching the right way to wear a pocket square. (Spoiler alert: step one was to ditch the Kleenex and buy some actual pocket squares.)

In this post I’ll share everything I’ve learned, and show you how to wear a pocket square with style, class, distinction and dapperness.

How to Wear a Pocket Square

A Primer on How to Fold, Wear and Rock the Classic Men’s Accessory 

The Three Main Types of Pocket Square Folds

Grey suit, black tie, white pocket square

After recognizing how much they can help you stand out, one of the first questions guys have is, of course, how to fold a pocket square.

That’s obviously important (and laid out step-by-step below), but wearing pocket squares – and more specifically, wearing them well – is about more than the technicalities of how to fold them.

It’s about understanding where and when to wear them for maximum effect. The good news is that you don’t need a degree in fashion design to master the ins and outs of pocket squares.

The real key is to understand the three primary pocket square folds, and when to employ each one.

1. The Classic Square

Don Draper smoking
Don Draper singlehandedly brought the classic pocket square into the 21st century

The safest and most classic way is to fold your handkerchief into a crisp rectangle that’s the same width as your breast pocket, and position it so that between 1/4 inch and 1 inch of the square is visible above the pocket line.

(See the “How to Fold a Pocket Square” section below for exact instructions on how to fold it to perfection.)

This look was popular in the 1950s and early 1960s, and was resurrected for the 21st century by one Don Draper (or more specifically, creator and showrunner Matthew Weiner) when Mad Men exploded onto our screens in 2007.

2. Exploding Awesomeness

Blue suit, brown vest, brown pocket square
Image: lookastic via Pinterest

Another popular (and decidedly less strait-laced) method is to ditch the square shape entirely and position the handkerchief as if it were almost exploding out of your pocket.

This method is most often used with silk handkerchiefs that feature a patterned or multi-color design, which helps give your suit – which many people think of being very serious and business-like – a fun pop of color.

3. The Loose Square

Grey suit, blue shirt and pocket square

My personal favorite pocket square fold is to split the difference with what I call the loose square.

You fold the handkerchief much like you would for the classic square, but you purposely misalign the corners to create a layered effect that stacks each individual fold on top of each other.

This pocket square style works especially well with white handkerchiefs that are lined with a color along the edges; stacking the corners on top of each other reveals more color, while the white base keeps the whole thing subdued and (in my humble opinion) sophisticated.


How to Fold a Pocket Square

Now that you understand each of the three main types of pocket square folds and where/when to wear them, the next key thing you need to know is how to fold a bandana or handkerchief so that it actually fits in your pocket.

Folding The Classic Square

One of the reasons the Classic Square has endured for so many years is because it’s also one of the easiest to fold.

Ties.com has a great series of videos and illustrations that shows you a simple five-step process for folding the Classic Square, which they call the “Presidential” pocket square:

How to Fold a Square Pocket Square Instructions
Illustration via Ties.com

Steps:

1. Begin with the pocket square face down
2. Fold in half from right to left
3. Fold in half from left to right leaving a gap at the right side
4. Fold in half from top to bottom
5. Fold the bottom up and behind the front. Adjust to fit the size of your jacket pocket.

Folding the “Exploding Awesomeness”

That Ties.com guide actually shows multiple pocket square folds that all fall under the umbrella of what I call the “Exploding Awesomeness.” But the one that probably exemplifies it best is what they call the Reverse Puff:

How to Fold a Puff Pocket Square Instructions

And here are the steps they recommend:

1. Begin with the pocket square face up
2. Pinch and lift up from the center
3. Run the fabric through the thumb and first finger of the opposite hand
4. Holding the center, flip the pocket square so that the peaks are facing up
5. Fold the bottom up and behind the front. Adjust to fit the size of your jacket pocket.

Folding the Loose Square

What I call “the Loose Square” Ties.com actually calls The Classic. (Apparently we don’t entirely agree on what constitutes “Classic.”)

The steps for folding it are very similar to the steps for folding the Classic Square listed above, but for this one you essentially put the pocket square in upside down, so that the edges stick out of the pocket.

It’s also worth noting that the instructions below assume you want all of the layers of the pocket square to be aligned, where as I like to purposely misalign them so the layers are a little more obvious.

How to Fold a Loose Square Pocket Square Instructions

Here are the steps:

1. Begin with the pocket square face down
2. Fold in half from right to left
3. Fold in half from bottom to top
4. Fold in half from left to right
5. Fold the bottom up and behind the front. Adjust to fit the size of your jacket pocket.


How to Nail Pocket Square Color

The Color Wheel and Circle of Pocket Squares

Should your pocket square color match your shirt? Your tie? Your suit?

Deciding what constitutes the “right” pocket square color is one of the most subjective and disputed topics in all of menswear.

There are some who swear that your pocket square color should sort-of-but-not-quite match your tie, and others, like Forbes‘ Michael Shannon, who insist it never should.

Personally I share GQ‘s belief that choosing a pocket square color is more of an art than a science.

And while there are few – if any – hard-and-fast rules in art, here are a few rules of thumb you can use to help guide your decision making.

1. Keep the Color Light

Man with pocket square adding a tie clip

The classic – and perennially stylish – pocket square style is the dark suit paired with a white pocket square.

Why? Partly because the lightness of the white pocket square nicely punctuates the dark suit, adding a touch of flare that helps the pocket square (and the guy wearing it) stand out.

When you branch out to experiment with other pocket square colors, keep the basic light-on-dark framework in mind.

It allows you to play around with the color wheel, while still paying homage to the classic look.

2. Try Tying it Into Another Piece of Your Wardrobe

Man with pocket square using phone
The red and orange colors of the pocket square pair nicely with the same colors in the tie

Whether your pocket square should match your shirt, your tie or none of the above may be a matter of some dispute, but personally I like to tie the pocket square into the rest of my getup in some way, shape or form.

Sometimes this means going for a multi-colored pocket square, and matching one of the minor colors in the handkerchief to my shirt or tie.

Sometimes it means opting to pair it with a different piece altogether; for instance, if you’re wearing a grey suit, white shirt, blue tie and brown shoes, you could opt for a brown pocket square (or, again, one with brown in it) that plays off your shoe color.

3. Go for Complementary Colors

Man wearing blue suit and orange pocket square

Instead of matching your pocket square to the rest of your outfit, you can also consider going in the other direction and opting for a pocket square on the other end of the color wheel.

For instance, blue and orange are complimentary colors, so if you’re wearing a blue suit with a white shirt, introducing an orange pocket square would add a fun pop of color that nicely complements the blue in your suit.


How to Wear a Pocket Square in a Suit

Neal Caffrey wearing a pocket square
Don Draper may have brought the pocket square into the 21st century, but Neal Caffrey wore it to perfection

Any of the three pocket square styles laid out above can work when wearing a suit, but it’s important to consider the context.

As a rule of thumb, the Classic Square pocket square should be used in more formal or professional environments (think funerals or serious workplaces like law firms and banks).

Consider the Context

For instance, on the show White CollarNeal Caffrey always opted for the straight square fold, which befitted the formal atmosphere of the FBI office he worked in.

But the more celebratory or fanciful an event is, the more fun you can have with your pocket square.

For weddings, bar mitzvahs and anniversary parties, consider going for Exploding Awesomeness, the Loose Square or the Rolled Thunder (explained below).


How to Wear a Pocket Square with a Tuxedo

Man in tuxedo wearing white pocket square

I have to admit I’m jealous of anyone searching for how to wear a pocket square with a tux, because in the more casual world we live in, dressing up for black tie events is an increasingly rare occurrence.

When it comes to rules, pretty much all of the rules in the “How to Wear a Pocket Square in a Suit” section above apply to tuxedos as well, but with tuxes there’s an additional – and extremely important – caveat: keep the color white. 

Tuxedo Pocket Square Color

A white pocket square paired with a midnight blue tuxedo
When wearing a pocket square with a tuxedo, always keep the color of your shirt and square white

This is the one area where choosing the right pocket square color is clear.

Whether you opt for the Classic Square pocket square fold or one of the more playful alternatives, when wearing a pocket square with a tux, make sure you keep the color of your pocket square consistent with the color of your shirt, which, when you’re wearing a tuxedo, should definitely be white.

Tuxedos themselves were of course traditionally black, but nowadays can come in a wide range of colors. (For my wedding I wore a midnight blue tux reminiscent of the one Daniel Craig wore in Skyfall.)

But regardless of what color you choose for the tux itself, a white shirt is always the most appropriate choice for a tuxedo, and your pocket square should follow suit.

Some of the non-square pocket square folds can look just as classy and debonair as the traditional fold, and therefore work just as well with a tux, but any color other than white will look too informal, and clash with the otherwise dignified nature of the rest of your look.


How to Wear a Pocket Square Casually

Man wearing blue blazer and casual pocket square

Pocket squares are often paired with suits and tuxedos, but that doesn’t mean they can’t be worn casually with blazers and sports jackets, too.

In fact, wearing a casual pocket square is arguably even easier than wearing one with formal attire, because you can loosen up on a lot of the rules of thumb mentioned above and have some fun with it.

Rules Shmules

When wearing a pocket square casually, opt for any fold other than the Classic Square, to keep the look feeling fresh, light and easy rather than buttoned down and formal.

You might also want to consider throwing everything I said above about color out the window, and use the pocket square to introduce a fun, bold print or pattern that has nothing do with the rest of your outfit.


How to Wear a Silk Pocket Square

Circle of pocket squares

As mentioned above, the look that I call Exploding Awesomeness is one of the best options for silk pocket squares because it’s less structured and easier to pull off with a lighter weight fabric like silk.

But it’s not the only option. Silk pocket squares can also be folded into either the Classic Square or Loose Square, as well as a couple other types of pocket square folds we haven’t discussed yet.

The Diamond

Man wearing blue suit and white pocket square in diamond shapeAs its name suggests, the diamond is essentially an inverted square.

To fold the Diamond you use the same method as the Classic Square to fold the handkerchief or bandana.

But you turn it before placing it in the pocket so that one corner protrudes from the top, like an iceberg protruding from the ocean or a pyramid from the desert.

Rolled Thunder

Man wearing orange pocket square rolled in pocket

Though the name (which, admittedly, I just made up) may not be as obvious, rolled thunder looks just as dapper as the diamond.

To achieve this look, you don’t fold your pocket square as much as you, well, roll it. (Alright fine, so maybe the name isn’t any less obvious.)

Simply fold the pocket square in half, then stuff into your pocket folded-ends-first.

Like the Exploding Awesomeness, this is another style that works great with silk pocket squares, which tend not to fold as crisply as cotton.


Where to Buy Pocket Squares

Man shopping for pocket squares online

When guys ask me where they should buy pocket squares, my go-to answer is always the same: “online.”

To be honest, at this point pretty much all menswear can be bought on the internet (I’ve even been known to buy suits online), but pocket squares are particularly well suited for online purchasing: you don’t have to worry about sizes or fit, the quality of the fabric is important but not make-or-break, and they’re so light that the shipping fees are usually minimal.

Of course, once I explain all that, the next question guys usually ask is where they can buy cheap pocket squares online, so let’s look at a few options at both the top and the bottom of the price spectrum.

Where to Buy Pocket Squares Online

My two favorite places to buy pocket squares online are The Tie Bar and Ties.com. Both outlets specialize in men’s accessories and refresh their inventory frequently, meaning they always have cool new colors, fabrics, patterns and designs available, in addition to the classic styles.

Prices vary depending on the material and quality you choose, but both outlets offer everything from pricey one-offs to affordable multipacks.

A Couple Stylish Options:

Where to Buy Cheap Pocket Squares

And speaking of affordable multipacks, if you’re price-conscious one of the best places to buy pocket squares online is definitely Amazon.

As with everything else they sell, their pocket squares come in a huge range of colors, options and prices, including various types of multi-packs that cover just about every color on the spectrum.

Cheap Pocket Squares on Amazon:

Nail (the Rest of) The Details

Rocking a Pocket Square is a Good First Step—But There are Many More

Now that you know the ins and outs of how to wear a pocket square, you’ve mastered one of the many details that help a man look sharp and stand out.

But many is the operative word.

The (handsome) devil is in the details, and the guys that tend to look the best are the ones who pay attention to the little things and do them all to perfection.

Fortunately, you don’t need to guess which details make the biggest difference on your overall appearance, or how to get them right.

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