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Can You Put A Pocket Square In A Dress Shirt?

A pocket square is a great way to add a level of sophistication to your outfit. You may have considered buying one if you’re looking to impress. But the question is, can you put a pocket square in a dress shirt?

Pocket squares should not be worn in dress shirts as it’ll look out of place and cluttered. The pocket of a dress shirt would usually be covered by a jacket in any case. Traditionally, pocket squares should only be placed in the breast pocket of a blazer, suit jacket, or tuxedo jacket. 

While it can be tempting to experiment, avoid it. Sticking to the traditional options is a much safer play.

After going through the main reasons why you shouldn’t do it, we’ll discuss the better alternatives in a little more detail. 

Let’s get to it. 

pocket square collection
Image From Deposit Photos

3 Reasons Why You Shouldn’t Put Pocket Squares In Dress Shirts

Though it may seem logical to add a pocket square to a dress shirt as it, in theory, will help you look smarter and more refined, there are plenty of reasons why this is a bad idea. 

Let’s get into those now.

1. It Looks Too Cluttered

When it comes to looking good, simplicity is key. True style comes when simple concepts fit together to create a look that looks sophisticated and well-rounded.

A pocket square situated in a shirt pocket will often result in an unnecessarily cluttered look. Having a pocket square stuffed in your shirt pocket won’t add any value to your outfit – it just makes you look overdressed.

It’s also vital to keep your dress shirt free of any additional designs or trinkets. This will help you achieve the streamlined, clean look you’ll be looking for. Aim for simple colors and make sure your dress shirt is immaculate. 

2. Pocket Squares Are Designed To Be Seen In A Jacket

Your pocket square is designed to add a splash of color and character to a formal jacket or blazer. 

Subtle and charismatic, they rest inside the breast pocket and can be seen and commented on by people you speak to. 

man in black suit with pocket square
Image From Deposit Photos

Putting a pocket square inside your dress shirt pocket renders it pointless. Chances are, your blazer or jacket will completely obscure your shirt and your dapper pocket square will likely remain unseen for the duration of the event you’ve worn it for. 

A well-made pocket square deserves to be seen by others. Make sure you place it inside your blazer or jacket’s breast pocket for people to comment on it. 

3. Dress Shirts Are Too Informal For A Pocket Square

The whole point of a pocket square is to look both stylish and formal. They’re made to add subtlety and not distract from your overall outfit too much.

Dress shirt is too informal of an item for a pocket square to be placed within it. Your outfit will look poorly balanced and people will be left wondering why you didn’t follow convention and place it in its proper location.  

Where Should You Put Pocket Squares Instead Of In A Dress Shirt?

Pocket squares should only be placed in the breast pocket of a blazer, suit jacket, tuxedo jacket, or vest. Remember, however, that wearing a pocket square inside a vest is pointless if you’re wearing a blazer or jacket on top.  

Let’s dig into these a little more. 

Suit Jacket Or Blazer

For optimal results, it’s best to stick with tradition and place it inside your blazer or suit jacket’s breast pocket. That’s the area that pocket squares are designed for and, ultimately, where they look their best. 

Wearing a pocket square in your blazer’s breast pocket will also ensure your pocket square is observable to others without interfering with your overall look. 

A pocket square will most likely be a little too much if you’re wearing a suit jacket or blazer in a business-professional sense. 

You’ll probably come across as overdoing it if you wear one to work. 

But for those professional or business-casual social events where you want to make an otherwise pretty basic suit look a tad more dapper, a pocket square would be a great way to go. 

Tuxedo Jacket

A pocket square is a great addition to a tuxedo jacket and will take your sophistication to the next level. 

The reason it works is that the formality levels match perfectly. Both pocket squares and tuxedo jackets have an immediately noticeable formal edge and sophistication to them. 

It just works. Wearing a pocket square in a tuxedo jacket wouldn’t draw much attention at all. 

It’ll just look normal. 

However, when wearing a pocket square with a tuxedo jacket it’s important to keep things understated. You don’t want the pocket square to be the focus of the entire outfit. 

Instead, it should blend seamlessly into the entire tux aesthetic as a whole.  

Aim for a more subtle design, as a more eccentric-looking pocket square can clash with the tuxedo’s ultra-slick, formal, and no-nonsense look. 

Keep it simple and don’t overdo it. 

Vest

There’s a time and a place for wearing a pocket square inside a vest. Whilst it’s certainly possible to make it look good, there are some mistakes  you need to avoid. 

For starters, make sure that you don’t wear a blazer over your vest. This will, again, obscure your pocket square from view and render your pocket square useless. 

It’s perfectly acceptable to wear a pocket square inside a vest if you’re not wearing a jacket. If temperatures are hot outside and you opt to ditch your blazer, a smart vest with a pocket square is a great substitute. 

Bear in mind that it can sometimes look a little “incomplete” without a jacket on top. Almost like a 3-piece suit with the third piece missing. 

But it’s still a reasonable option if you don’t want to wear a full 3-piece suit and simply want to make the vest itself look a little more sophisticated. 

Conclusion

To sum up, a pocket square in a dress shirt doesn’t look particularly good. Keeping things simple and sticking to the more traditional choices is definitely the better option here.