When You Should (and Shouldn’t) Wear A Pocket Square

“Is there a time when you shouldn’t wear them?” I hear you ask…

If you prefer watching a video instead of reading this, have a look at this:

Seriously, how do you know when to wear it and when is it inappropriate?

Imagine this…

You are in the middle of a conversation about some serious topics with your newly acquired friends.

The conversation gets dark.

It becomes a serious one.

How does your yellow pocket square with blue ducks in the water look like now?

Let me guess…

Not serious enough for the conversation at hand…

You think now: “But that is just a bad choice of apparel and accessories for the occasion, right?”

Sort of…

But one time when you yellow pocket square with blue ducks is inappropriate is that serious conversations and meetings scenario.

What can you do instead?

Well, wear something classic.

White TV folded pocket square usually, will do the trick.

As pocket squares are known for adding a sense of refinement to any look. 

Therefore it’s even harder to think of an occasion in which they aren’t welcome. 


Once you start wearing them, it’ll seem weird to rock a blazer without one. 

But what are the other instances where a pocket square is inappropriate?

To start, let’s focus again on all the places you should wear a pocket square. 

If you’re putting on a blazer, sports coat, or suit, you should wear a pocket square. 


If you’re headed to a formal event, you should absolutely wear a pocket square. 


Even when you’re considering wearing an air tie, you should still wear a square. 

Most of the time.

In fact, in this instance, it’s mandatory to keep your look from falling flat. 

And regardless of what you’re wearing from the waist down, whether it’s denim, chinos, cords, or trousers, a pocket square still works.

pocket square casual

Pocket squares add a touch of refinement in every scenario. 

So to answer the original question, there really isn’t a time or place in which wearing a pocket square is inappropriate. 

Once you start wearing them, it’ll seem weird to rock a blazer without one. 

If anything, the way you wear it is more important.

How do I know?

Well, let me tell you that having nearly a 1000 different kind of pocket squares should tell you a lot about what kind of person I am.

One thing to remember…

As per the first paragraph of this article…

If you’re headed to a funeral or a sombre event, it’s probably not appropriate to sport a puff fold or a more complicated fold like the four-point.

Stick to TV fold.

Classic and Simple.

classic pocket square 

If you’re on your way to a more casual setting like a birthday party or a happy hour, the presidential fold might be a tad too formal. 

Yet still, squares are appropriate in all these scenarios. 

It’s just the styling that needs to be adjusted.

Here is the thing...

Back in 2009, Esquire lamented about the overuse of the pocket square and attributed its popularity to the rise of Mad Men

It seemed every guy, regardless of his fashion know-how, was incorporating the square into his everyday style with mixed results. 

While the storied men’s magazine didn’t exactly denounce them, it offered alternatives for tweaking little details in place of a square.

Why does it matter?

Instead of an adventurous fold, the mag suggested some boldly patterned statement socks or a unique pant cuff. 

But there is a catch…

That same piece also advocated for skipping the pocket square at certain times. 

The best part?

For the guys out there who want to scale back their accessory options, know that you can. 

You can leave your breast pocket empty and play with other details. 

But if you’re heading out sans pocket square, make sure every another element of your look is killer. 

Without a square, you’ll probably want to skip wearing a tie as well. 

And you’ll need to make sure your shirt colour is bold enough to stand on its own.

It is all about balance…

balanced pocket square


Not to mention, your suit should be so stellar that no one even notices the absence of your square.

In other words…

it’ll be tough to look sharp without a square. 

There’s really no occasion where a pocket square would be deemed unnecessary or inappropriate. 

It’s all about how you style it and work it into your look. 

If you adjust your fold or your colour for each specific event, your square will always be welcome.

You can get yours here:

Yellow Black Pocket square

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