How to Wear Pocket Squares Like a Pro

Pocket squares: Once the forgotten kids of men’s fashion, they have made a spectacular comeback. It seems like they are here to stay!

They are an easy and beautiful way to upgrade your formal or casual looks. It will give a stylish touch to any conservative suit and will create color contrast.

They come in silk, cotton, linen or wool, and have a wide range of patterns and colors. You can wear them with bow ties, neckties, or alone.

And we do understand if you’re a little bit afraid of wearing them! Maybe you weren’t even aware you could use pocket squares.

It’s true we never had class at school called “Folding Pocket Squares 101,” let alone “How to Wear Pocket Squares.” I’m sure you have been tempted to wear a pocket square, but you want to make sure you do it like a pro, right?

Don’t worry. We’re here to give you a hand. We will show you some helpful suggestions on how to build your looks using pocket squares.

Before we begin, please remember: This is not a hard set of rules. Think about your personality and style. Just consider this text as a source of inspiration. You can always take these suggestions and make them your own :)

Are you ready to take your style journey to the next level?

A Little Bit of History About Pocket Squares

Need to clean the sweat off your head? Blow your nose? Clean your hands? Before pocket squares became a fashionable object, they only had a hard-working cousin that served various purposes: The handkerchief.

There is evidence that, as early as ancient Egypt, handkerchiefs existed. Greeks and Romans also had them.

Greeks would impregnate handkerchiefs in perfume to avoid funny smells. Romans started their gladiator battles when the emperor dropped a tissue to the floor.

As you can see, the handkerchief had different uses and symbolic meanings.

But it seems like pocket squares were born with King Richard II of England. He started wearing a handkerchief not only to blow his nose. After that, handkerchiefs were embroidered or made in silk to show status.

By the 19th century, men realized carrying the handkerchief in their pants pocket wasn't the best. Coins weren't the cleanest things in the world! That’s how they started putting their tissues in the front pocket of their jacket.

Eventually, this handkerchief became a decorative detail. This might make you infer you should have a hanky for utilitarian purposes. Your pocket square should never serve your nose!

During the 20th century, the popularity of the pocket square was on and off. Some famous actors like Fred Astaire and Cary Grant made it a fashion article. But it seems like it lost its shine as clothing became more casual.

Now, pocket squares have reappeared to give style to your clothes. The funny thing is there are affordable pieces so you can upgrade your looks for an excellent price. How can you say no to pocket squares?

Squaring Up Your Pocket Squares

So let’s talk about some important things to keep in mind when you decide to wear a pocket square.

You can always wear pocket squares with suits or sports jackets, from the most formal to a casual occasion. However, never add a pocket square to an overcoat, coat or shirt as this will look out of place.

Now the matching part! What fabrics are the best? How do you match your pocket squares to fit your whole outfit? Which colors or patterns should you look for?

There’s a full range of possibilities, and we’ll talk about some places where you can start. From there, you can decide what works best.

Fabrics

Usually, pocket squares come in silk, linen, cotton, and wool. The most important thing is to choose a pocket square that is not too thick or too big. This might make it look bulky on your pocket.

Silk pocket squares are the most elegant and year-round material. They are the most expensive ones.

Linen and cotton are easy to fold, and they are suitable for spring and summer weather. Wool, cashmere or flannel are suitable for colder months.

Matching Tips

Pocket squares are very versatile, and there are plenty of options to juggle, with. Maybe we can start by telling you what NOT to do.

One of the no-nos is to match the pocket squares exactly to your tie or shirt. Since the idea of the pocket square is to innovate and be creative, there’s not a point in matching all colors.

Your pocket square could have as secondary color the primary color of your necktie. But never choose for pocket squares the same exact color or pattern as your tie or shirt.

For more conservative looks, look for lighter or darker shades of the same color on your jacket, shirt or tie.

For bolder looks, go for complementary or contrasting colors on the tie, shirt or jacket, and pocket square.

Do not try to mix too many patterns or different types of fabrics at the same time. For example, go for a solid color in your jacket and shirt.

Then, you can play a bit with the patterns in your tie and pocket squares. For instance, go for a striped tie and patterned pocket square.

If you choose to combine different patterns, please add different scales to create a contrast. For example, if your tie has thin stripes, your pocket square could also be striped, but they should be thicker ones.

Now let’s check some of the options you have regarding colors and patterns for pocket squares: 

White Pocket Square: It is the most classic pocket square every man should have. In a flat fold or presidential fold (folded in four smaller squares), it will be your workhorse.

It is perfect for formal and business occasions. You can never go wrong with a white pocket square.

Pocket Squares With Tipping: These pocket squares give you a hint of color. You can opt to match your shirt to the tipping of your pocket squares for a dope look.

Solid Pocket Squares: The solid color pocket squares are easy to match with your jacket, shirt, and tie. Again, go for darker or lighter tones concerning your other pieces. They complement or create contrast with your look.

Patterned Pocket Squares: Striped, polka dots, gingham (checked) or the craziest decorations you can think of. These are pocket squares that will give you a more flamboyant or bold look, but they might be harder to match.

It is advisable to start with solid colors or subtle patterns if you’re not sure.

Folds

Folding pocket squares is like origami. There are a million ways to do it. Of course, merely folding your pocket square as four squares (the flat or presidential fold) is the most conservative way to do it.

From there, you can experiment with different folds. Of course, the more complex the fold, the riskier your look is. For a tutorial on how to do different folds, click here.

3 Types of Attire With Pocket Squares

To give you some fun and versatile ideas on how to match pocket squares, we’ve created some looks for formal, business casual and casual wear. You will see each look along with four different pocket squares to wear. Check it out:

Formal Look

We have chosen solid colors for the suit and shirt. This way you can play around with the patterns of the tie and the pocket squares.

The dark blue pocket square with polka dots and white border matches the colors of the shirt and the primary color of the tie.

The red pocket square with polka dots and white border also matches the shirt. It also gives a bit of contrast with the blue and charcoal color of the suit.

Finally, the patterned dark blue pocket square with white border matches shirt and tie. It also creates a contrast because of the golden details.

To complement your whole outfit, wear Oxford shoes in black. 

Business Casual Look

Again we’ve chosen to go with solid colors for shirt and tie. We already have enough contrast between the chinos and the sports coat.

The white pocket square with navy blue matches the jacket.

The mid-blue pocket square with white details creates a conservative contrast with the navy blue in the jacket and light blue in the shirt.

The bolder patterned pocket square has tips of blue. But the orange also complements the blue tones of the whole outfit. The khaki color in the pattern also matches the chino.

FInally, wear Monk Straps in brown to give contrast to your chinos. 

Casual Look

The light gray sports coat and the white polo shirt are a white canvas. You can go creative with your pocket squares here!

The dark brown pocket square with white details creates contrast with the dark grey/olive pants.

The red striped pocket square complements the grey/olive pants. It gives contrast to the jacket and shirt as well.

The other two pocket squares have gold, and blue shades are fun. Also, they create a contrast with the different colors of the outfit. Give a final touch with white sneakers.  

Conclusion

As you can see, the humble pocket square can add an exclusive look to your outfits without pushing it too hard.

It will allow you to express your personality when everybody seems to be wearing the same kind of outfit. The colors, patterns and the way you fold your pocket square will say a lot about your attention to details.

If you are jumping into the waters of pocket squares for the first time, keep it simple. Go for white, tipping, or solid colors.

If you are an intermediate swimmer and feel confident enough, get some patterned pocket squares. Always make sure to create contrast with the other pieces you are wearing.

Overall, remember not to exactly match the color of your pieces and your pocket square. Then, you'll be one stroke away from your own style!

All pocket squares and clothing pieces are from SuitSupply. Check their great catalog here! 

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