The Sharp Gentleman Guide to Pocket Squares

We have recently seen a resurgence of pocket squares in menswear, and I couldn’t be happier. Honestly, it’s one of my favorite go-to items that instantly enhances your style. Unfortunately, there are still men out there wearing suits with the pockets still stitched shut.

Cut the pockets open, gentlemen.

Adding a pocket square is such an easy way to immediately add class and presence to your ensemble. Who knew this little piece of fabric would make such a difference in personal style? More importantly, where did it come from? Is it just a handkerchief men decided was best used ornamentally? When did that start? Here’s a bit of backstory and a definitive guide to pocket squares top help you figure all that out.

Let’s dig into a little history

guide to pocket squaresPocket squares began as handkerchiefs. The jury is still out on exactly when and where they began, but history tells us that the ancient Egyptians made small linen cloths for decorative purposes around 2000 BCE. Around 250 BCE, gladiators would parade the Coliseum and call to the Emperor before battle, shouting, “Hail Caesar! They who will die, salute you!” A magistrate would then drop a ceremonial handkerchief called an orarium to signal the start of the games. Today’s priests wear a larger and much more detailed version of one.

Fast-forwarding to a little more modern time, King Richard II (England) is credited with “having a little piece of cloth for the lord king to wipe and clean his nose” in the late 14th century. This was the true start of the handkerchief. Later on in France, Marie Antoinette –Louis XVI’s wife– was quite bothered by the random, and sometimes unnecessary proportions of the handkerchiefs she was seeing. Knowing that a happy wife makes for a happy life (especially when it’s Marie freakin’ Antoinette), King Louis declared in 1785 that all handkerchiefs must measure equally in length and width – giving us the square portion of pocket square.

guide to pocket squaresMoving into the 1900s, the world began to witness the birth of the modern pocket square. What I mean by that is now men were carrying two cloths instead of one. They continued to carry a handkerchief in their trouser pocket, but now also had a beautifully folded cloth of linen, cotton, or silk tucked into the breast pocket of their jacket. The cloth in the jacket was a symbol of class and character. The cloth in the pocket was for wiping your brow, your nose, or anything else that needed wiping – within reason, of course.

As fashion relaxed in the mid 20th century, the pocket square (and pocket watch), handkerchief, and hat (bowler, fedora, etc.) faded out. Even a mild resurgence in the 1980s wasn’t enough to make it cool again. Then again, the 80s contained some of the worst fashion designs the world had even seen. Parachute pants? Shoulder pads? 12-pleat trousers?

Oh my God, no.

The true return came from our obsession with television. Mad Men hit screens all over America and suddenly it was cool to have a pocket square. It was cool to like Scotch and be gentlemanly. The show came on and introduced men to tailored suits and quiet class. Pocket squares were simple, but always included. For that, I’m thankful. That, and Christina Hendricks.

The best part of what makes a pocket square so powerful is that it is the most affordable and easiest way to instantly enhance your style. There are companies all over the world making pocket squares in sizes from 10″–16″ in a myriad of different fabrics and patterns. Moreover, they can be had for as little as $10. Yes, there are cheaper squares on the internet, but are you really that guy? Are you going to let $10 be too steep for you? Hell no, you’re not. Good.

Important Fashion Note

You want to enhance your look with a pocket square, and that means you want to accent colors you’re already wearing; not match them. This means generally, a pocket square should complement your shirt or tie but rarely, if ever, directly match it. When matching a color in your tie, shirt, or jacket, it should always be a minor, or secondary color. When you get all matchy-matchy, it looks ridiculous. Recent Sundays have shown the usual roundtable of sports announcers giving the play-by-play from the studio, and they’ve had pocket squares that match their ties. That’s a big no-no, Mr. Bradshaw. You can do better.

Most Popular Pocket Square Folds

Now that you’ve decided to pick one up, you need to know how to fold it in all the right ways to make gentlemen jealous and ladies swoon. Just to be clear, I cannot confirm that, in fact, ladies will swoon over you now that you’ve got a pocket square. I’m not magical. You may need to dapper up other parts of your game. My friends over at The Art of Manliness created the stellar infographic below, and I wasn’t about to reinvent the wheel, so check it out!

guide to pocket squares

Just remember, a pocket square is a simple way to dress up just about any jacket. As long as you don’t directly match your tie, or have a bed sheet stuffed into your breast pocket, you’ll look dapper in every setting.

Do you have a go-to color, fabric, or fold for your pocket square? Share in the comments below so we can connect!


Previous post

What Happened When I Lost My Dad

Next post

The Sharp Gentleman Guide to Drinking Scotch Whisky

The Author

Blake Hammerton

Blake Hammerton

Blake Hammerton is the founder and coach at The Sharp Gentleman, and helps men earn more respect while gaining confidence in who they are. He is a certified relationship coach and loves writing about men's fashion, style, character-building, relationships, travel, adventure, and more.