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The Ultimate Pocket Square Guide for Men

June 15, 2022 8 min read

Extreme Cutaway Shirt for Men From Dandy and Son

Some might say that looking dapper is an art form, but one of the simplest ways to up your style game is with a pocket square. A pocket square adds a touch of refinement and can really make an outfit pop.

While many men think that pocket squares are only for formal occasions, they can actually be worn with a variety of looks. In this handy pocket square guide, we'll show you how to pick the perfect pocket square for any outfit and occasion.

Whether you’re going for a classic or more contemporary look, read on to learn everything you need to know about pocket squares! 

How to fold a pocket square Dandy and Son
Photo by Steven Ungermann on Unsplash

What Is a Pocket Square?

A pocket square is a rectangular piece of fabric that is folded and inserted into the chest pocket of a man’s blazer or jacket. Pocket squares can be made from various materials, but the standards are silk, cotton, linen, and wool.

Like mentioned above, the standard pocket squares are normally rectangular, however they do come in a variety of sizes and styles and can be folded into many different ways. They are typically used to add a touch of refinement to an outfit and can make a big impact when worn correctly.

Even though a pocket square it is mostly seen in formal settings like weddings or black-tie events, pocket squares are also becoming increasingly popular in more casual settings. With the right pocket square, you can really make any outfit pop.

History of Pocket Squares

Pocket squares have been around for centuries, and the history of pocket squares for men is fascinating!

The first kind pocket squares were likely used in Ancient Rome, Greece, and/or Egypt. These early pocket squares were made from white linen handkerchiefs and were used to wipe sweat and dirt from the face.

The pocket squares really came into fashion in the 14th century when King Richard II was seen wearing one in a portrait. King Richard II is considered the inventor of the pocket square as a fashion accessory, and his style soon caught on with other noblemen of the time.

Fun fact, did you know that pocket squares were initially placed in the trouser pocket? It wasn’t until the 19th century when pocket squares started to become popular as part of men’s fashion and. This was when two-piece suits started to become popular, and men began tucking their pocket squares into the chest pocket of their blazers or jackets.

Pocket squares reached the height of their popularity in the early 20th century. They were seen as a bona fide fashion accessory and were worn by many well-dressed at the time.

There are various factors that have contributed to the rise in the popularity of pocket squares. One reason is that they are a very affordable way to add personality and style to an outfit. Pocket squares are also versatile, meaning they can be worn with many different looks. While pocket squares fell out of fashion in the mid-20th century, they have made a comeback in recent years and are now more popular than ever!

Pocket Square Guide 2022 Dandy and SonPhoto by Andrew Neel on Unsplash

Types of Pocket Squares and Folds

Just like ties, there are many ways to fold a pocket square, some are easier than others.

The most popular folds are the presidential fold, the one-point fold, the two-point fold, and the classic puff fold.

Presidential Fold

The presidential fold is a classic look that is perfect for formal occasions. To achieve this look, fold the pocket square in half and then in half again. Next, fold the pocket square into thirds and tuck it into your jacket pocket. 

One-Point Fold

The one-point fold is a simple yet stylish way to wear a pocket square. For this look, fold the pocket square in half diagonally and then fold it in half again. Tuck the pocket square into your jacket pocket so that only one point is visible. 

How To Fold A One Point Pocket Square Dandy and SonPhoto by Cinematic Imagery on Unsplash

Two-Point Fold

The two-point fold is a great way to add personality to any outfit. The Two-Point fold can be achieved by folding the pocket square in half diagonally and then folding it into thirds. Tuck the pocket square into your jacket pocket so that two points are visible.

Puff Fold

As the name suggests, the puff fold is a bit more elaborate than other pocket square folds. This look is achieved by folding the pocket square into a triangle and then folding it into thirds. Next, take the pocket square and pinch it in the middle to create a “puff” effect. Tuck the pocket square into your jacket pocket and adjust as needed.

There are a number of other folds that you can experiment with, too! Be creative and have fun with it. You can find many video tutorials online on how to fold pocket squares online, or you can ask your tailor for help.

How To Fold A Puff Pocket Square Dandy and SonPhoto by Dane Deaner on Unsplash

Things To Consider When Deciding What Kind of Pocket Square to Wear

When deciding what kind of pocket square to wear, there are a few things you should take into consideration. Here are a few things to keep in mind:

1.   The Occasion

The occasion is a very important factor to consider when choosing a pocket square. Whether you’re attending a black-tie event or a casual outdoor barbecue, there’s a pocket square that will fit the occasion.

If you’re attending a black-tie event, you’ll want to choose a silk pocket square that is dressy and formal. A classic white color pocket square folded in the Presidential style is always a safe choice.

If you’re going to a more casual event, you can be a bit more creative with your pocket square choices. A fun printed pocket square or one in a bright color can add life to an outfit. You can also experiment with different fold styles, such as the One-Point fold or why not try the Four-Point fold. 

How To Fold A Four Point Pocket Square Dandy and SonPhoto by Nicole Geri on Unsplash

2.   The Color of Your Suit or Jacket 

The color of your suit or jacket is another important factor to take into consideration when choosing a pocket square. You’ll want to make sure that the pocket square you choose complements the color of either your jacket or the dress shirt you are wearing.

If you’re wearing a suit in a darker color, you’ll want to choose a pocket square that is light in color. A white pocket square is always a good choice, but you can also experiment with other light colors such as cream, beige, or why not pink. And, if you’re wearing a contrast collar shirt, why not match the pocket square with the color of the collar. 

3.   The Pattern of Your Suit or Jacket

The pattern of your suit or jacket is another important factor to consider when choosing a pocket square. If you’re wearing a suit or jacket with a busy pattern, you’ll want to choose a pocket square solid colored pocket square complementing your suit. This will help create a more balanced look.

However, if you’re wearing a suit or jacket with a simple pattern or no pattern at all, you can easily get away with choosing a pocket square with a more intricate design. Just be sure that the pocket square you choose does not have the same exact pattern as your clothing. Otherwise, it will be too matchy-matchy! 

4.   The Season

The season could also be an important factor to consider when choosing what pocket square to wear. If you’re wearing a suit or jacket in the spring or summer, you’ll want to choose a pocket square made from a lightweight fabric such as linen or cotton. But if you’re wearing a suit or jacket in the fall or winter, you can choose a pocket square made from a heavier fabric such as wool or silk.

5.   Your Personal Style

Your personal style should always be taken into consideration when choosing a pocket square. If you prefer a more classic and timeless look, you’ll want to stick with a pocket square in a solid color. If you prefer a trendier and fashion-forward look, you can experiment with different colors, patterns, and fold styles.

The most important is that you feel comfortable. This doesn’t only apply to when choosing what pocket square to wear. The same thing goes for when you are choosing what suit or dress shirt for men to wear!

Extreme Cutaway Shirt Pocket Square Dandy and SonExtreme Cutaway Shirt from Dandy and Son with Pocket Square

Pocket Square Rules Every Man Should Follow

1.   Never Match Your Pocket Square to Your Tie

You might be tempted to match your pocket square to your tie but resist the urge! Tie and pocket square combinations are major fashion faux pas. Instead, you should always choose a pocket square that contrasts, yet compliments, your tie in both color and pattern.

For example, if you’re wearing a striped tie, you would want to choose a pocket square in a solid color. Maybe one of the colors that can be seen in the tie?

2.   Don’t Be Afraid to Experiment

There are no hard and fast rules when it comes to pocket squares. So don’t be afraid to experiment with different colors, patterns, and fold styles. The best way to find a pocket square that works for you is to try out different looks and see what you like best! For example, you can pair a classic white Extreme Cutaway Shirt and black suit jacket with a pocket square in a bold color or pattern. Or you can try out a new fold style with an otherwise simple outfit. 

3.   Know When to Fold and When Not to Fold

There are two schools of thought when it comes to folding pocket squares. Some men prefer to fold their pocket squares neatly, while others wear them a bit more adventurous, like a puff fold. There is no right or wrong answer here. It all comes down to personal preference.

If you do choose to fold your pocket square, there are many ways to do it, some which we have already covered in this article. Just be sure that the pocket square you choose is big enough to be folded into the shape you want. Otherwise, it will look too small and out of proportion. 

4.   Keep It Simple

Just like most fashion accessories, sometimes less is more. You don’t want your pocket square to overshadow your other clothing or accessories. Instead, you want it to complement your overall look.

5.   Have Fun with It!

Remember, fashion is all about having fun and expressing yourself. So don’t be afraid to experiment with different pocket square styles. The most important thing is that you feel confident and comfortable in what you’re wearing!

How To Fold A Pocket Square Dandy and SonPhoto by Tyler Harris on Unsplash

Find the Perfect Pocket Square for Your Style

Now that you know all there is to know about pocket squares, it’s time to start shopping for one! We understand that the overwhelming number of choices can be daunting. But don’t worry, we’re here to help you find the perfect pocket square for your personal style.

Here at Dandy & Son, we have a wide selection of pocket squares in different colors, patterns, and fabrics. Whether you’re looking for a classic white pocket square or something a little more daring, we have what you’re looking for.

Pair your chosen pocket square with one of our 100% cotton shirts, maybe an Extreme Cutaway Shirt for Men, and you’ll be sure to make a lasting impression!

Double Breasted Knitted Cashmere Jacket Dandy and SonWhite Cutaway Shirt, Cashmere Jacket & Pocket Square from Dandy and Son

Finally…

Thank you very much for reading this article about pocket squares. Would you like to read more articles about dress shirts for men and men’s formalwear? Then head over to our blog!