What To Wear With A Pocket Square – Dress Shirt or Vest?

Can you wear a pocket square with a dress shirt?

Can you wear it with a vest?

Is it meant to be opened like they are on suits?

Let's talk about each of the four garments:

1. Shirts
2. Vests
3. Jackets
4. Overcoats

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.

If you want some more information on the difference between a pocket square and a handkerchief, go read this informative article on that topic:

Handkerchief Vs Pocket Square | Differences Between Handkerchief's and Men's Pocket squares

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 thing is I can still remember what it's like starting to find your own sense of style and this book is my way of giving back to all those gentlemen who helped me find my way and helping those of you who are now where I was when I started out.

The Pocket Square Itself

Personally I always wear a pocket square.

If 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!

Pocket Square Rule 1. Shirts With Pocket Square

The men's dress shirt is probably the closest to the body so pretty much, I say never.

I don't like the look. I've seen some guys try to pull it off but really a shirt breast pocket? I don't even like making shirts with breast pockets. I usually recommend men not to have it. And even if you buy something off-the-rack, a lot of times, you can remove the pocket as well.

There are many reasons to have a pocket.

I've got a good friend in sales and he's always moving and he keeps pens in it. In fact, the shirts I make for him have special pockets on the inside for holding his pens. He doesn't really use ones that leak ink, so I don't think he's ever actually lost a shirt, to those of you that object to that.

But if you use it, go for it but don't stuff it with a pocket square.

Pocket Square Rule 2. Vests With Pocket Square

My answer is you can wear a pocket square with a vest sometimes.

No – If you're wearing the vest under a jacket.

Yes – If you're wearing the vest by itself.

I've seen the latter being done by a lot of men.

I've got a good friend who's a  photographer. He's at weddings all the time so he wants to have his arms free because he's moving and he uses the pockets to actually hold pieces of gear but still he wants to look good.

I think he wears a bow tie with the pocket square and it looks good. Wearing a bow tie with a pocket square just shows that he went the extra mile but at the same time, he's at work so he follows the function path.

I always believe function first, style second. So in that case, it looks great.

Pocket Square Rule 3. Jackets With Pocket Square

I think a jacket should always be worn with a pocket square.

I know it takes a while for guys to get used to it. I have a client over in Dubai named Sandiv. He talked about how he just left the other day and forgot his pocket square.

He actually stopped at a store to buy one because he felt incomplete without it. When you can get to that feeling, it's a great place because people notice these pocket squares.

Start off small.

Start off with white.

We look at pictures of Harry Truman. He was a haberdasher before he became president of the United States.

The guy knew how to dress and look good. He always had that little square fold there.

Pocket Square Rule 4. Overcoats With Pocket Square (Trench coats and any type of jacket)

Here is where function happens. An overcoat is there to protect you when it's cold outside. No need for a pocket square there. Most likely, you're wearing a jacket underneath and that's where you would have the pocket square.

You may say, “Well, why does it have a breast pocket?”

That's where you could possibly put your gloves or to put sunglasses or something in that pocket. It's not really so much for adornment. That one is more for function.

And there you have it.

I talked about the four points:

1. Dress shirts – Never.
2. Vests – Sometimes especially if you're wearing it by itself.
3. Jackets – Always.
4. Overcoats – Rarely.

I'm answering a lot more questions there.

I also love seeing you guys in the comments section over at Real Men Real Style‘s YouTube Channel and if it's a great question, we'll make a video out of it.

Thanks and I will see you guys in the next post.

Learn how to do the Presidential Fold with your pocket square – How To Fold A Pocket Square | The Presidential Fold | Improve Your Style With ONE Item

Learn 9 ways how to fold a pocket square here.

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