How to Start Wearing a Pocket Square

What is a Pocket Square?

A pocket square is simply a square piece of fabric that gets folded up in different ways and put into your top jacket pocket.

Why Wear a Pocket Square

Wearing jackets is making a comeback as men like you realize denims and baseball caps are not appropriate for all occasions, but most men who wear jackets like sports jacket, suit jackets and blazers still don’t wear pocket squares.

When it comes to wearing pocket squares there are few men that make that conscious decision not to wear a pocket square – most men don’t because they don’t even know it’s an option.

This could be because they just haven’t noticed them before or they simply haven’t considered them as a vital part of their style arsenal.

I spoke to some men about pocket squares and I found that many of them were a little bit concerned to draw attention to themselves in this way, which is ironic because by simply wearing a jacket you’re already drawing attention to yourself.

The whole point of a pocket square is to give you the way and the means to stand out in a room full of other men wearing jackets and give you a further way of expressing your personality through your clothing.

The Pocket Square Itself

Personally I always wear a pocket square.

military-pocket-squareIf you look at the picture of me here you can see that the one I’m wearing is a bit different from what you’ll usually see. The difference is that this is a military pocket square made by Christopher Costa from Pocket Square Heroes.

Can anyone guess what this pocket square represents?

Now that I pointed it out you know this specific pocket square is not just a decoration but that it sends a message to those in the know.

You see that’s the brilliant thing about pocket squares – once you start to wear them you’re going to look around you and notice that this is something most well-dressed men who pay attention to details wear.

Wearing a pocket square is sending the signal you’re a man who cares about the details!

The Pocket Square as Conversation Starter

The best thing for me about pocket squares is that they are an effective conversation starter.

What’s amazing about this is that conversations are the beginning of essentially everything.

Think about it…..every great human achievement was started by a conversation between the men and women that achieved them.

The Egyptians didn’t just all pitch up at the right time and place and start building the pyramids.  No, it most likely started with King Djoser and his adviser Imhotep sitting around with nothing to do and King Djoser saying something like:

“Hey, Imhotep. That’s a really boring skyline don’t you think?”
“Whatever your majesty says.”
“Okay, just skip the formality for a second – what do you think?”
“Indeed, Your Majesty. It is a rather flat and boring skyline.”
“So what do we do about it, Imhotep?”
“Maybe we should build something – something big, Your Majesty?
“Hmm… What like four stories high?”
“No, Your Majesty: Bigger, much bigger.”
“You think? But that could take years to build and we’d need to use thousands of slaves.”
“Indeed and it would cost a fortune in money and resources. But if we make it big enough everyone will marvel at it for generations to come…”
“Hmm… That sounds great! Where do I come up with these great ideas, Imhotep?”
“You are simply that great, Your Majesty.”

* I may have gotten a few of the details wrong but you get the point.

Pocket Square

If you’re like many men you may not be confident enough to just walk up to a complete stranger and strike up a conversation.

You need some kind of “in” and if you’re in a room full of suit-wearing men suits are not really an effective entry strategy. But if you notice one of those 10 or 20 men wearing a pocket square you have your “in” right there.

Of course if you’re wearing a pocket square that just opens up all kinds of possibilities.

How Pick Your First Pocket Square

Now that we know what a pocket square is and why you should wear one you need to get started wearing one and my advice is to keep it simple in the beginning.

What you should start with is a simple white pocket square that you can find at any menswear store or men’s department in a larger store.

Your first one doesn’t have to be cotton or linen though my preference in pocket squares is to always go with natural materials and a lot of pocket squares are even made from silk.

For this first pocket square it does not even have to be perfectly folded. You can just start with a simple square fold which is referred to as a presidential square fold.

Then you just put in your pocket and pull it out a little so that just a little shows or you can pull it out a bit more if you want.

Starting to Wear A Pocket Square

Congratulations! You now have a very simple pocket square.

I always like to have pocket square in each jacket and you’ll find that all my jackets in the studio have a pocket square all ready to go.

This way when I throw on a jacket I don’t have to think about it and I don’t have to wonder about which pocket square I’m going to use.

So you’re sporting your first pocket square and you’re ready to head out into the public.

Man Wearing Jacket with Pocket Square

My first advice is that if you feel really uncomfortable wearing it just take it out. Remember that it’s all about confidence and if you’re not comfortable it’ll come through in your confidence level.

What will most likely happen is that you will go through the whole day and not really think about it until you realize you’ve made it through an entire day wearing a pocket square.

What will make you feel really great is when you start to get compliments and this is sure to happen.

You may hear comments like: “Hey, you’re looking sharp.”

People will not necessarily compliment the pocket square itself but just that little bit of contrast will grab the attention of people around you and remind them that you pay attention to the details.

Branching Out With Pocket Squares

Once you’re more comfortable you can eventually drop the square fold (which is one of the most formal folds) and try something like “The Puff’ (which is my favorite) or the Scallop.

Finding Your Pocket Square Style

Once worn either of these two types it’s important that you try out all the different styles and types until you find something you like and that resonates well with your personal sense of style.

Try combining different color squares with different types of folds and mix and match them with different jackets until you find something that works for you.