When to Wear a Pocket Square

Fashion / Tips for Him
Teodora Cozma
On Nov 17th, 2021
Pocket Squares

The foundation for the modern gentleman to navigate the etiquette of wearing a pocket.


Welcome to one of the most exciting mini-series about men accessories and explore with us four big questions about men's pocket squares. We will start the Pocket Squares mini-series by answering some of the most common questions about pocket squares, such as when to and when not to wear one, formal versus informal attire, and the pocket square's role in men's fashion.

What Is a Pocket Square

A pocket square is a square piece of fabric used as an accessory in men's attire. The pocket square was popularised by King Richard II in the 14th century and was initially used for hygiene reasons.

Later, the demands of style led to the evolution of the piece of cloth into different shapes, fabrics (including lace) and patterns. Finally, in France, through the decree of King Louis XVI (1754 – 1793), all handkerchiefs were standardised to have four sides of equal length.

Initially, handkerchiefs were kept in the trousers' pockets. However, as two and three-piece suits came into fashion, jackets were cut with a left breast pocket, displaying the handkerchiefs.

The popularity of the suits represented a revolutionary moment in pocket square fashion history, and the cloth shed its original purpose and became an accessory to express the individuality and style of the wearer. A gentleman will wear one for hygiene reasons in his hidden pockets and one for show.

Dressing well is a form of good manners.

Tom Ford - fashion designer

Pocket Square vs Handkerchief

Do not confuse a handkerchief with a pocket square! A handkerchief is a piece of cloth used by a gentleman for hygiene reasons. Therefore, it always resides in the hidden pockets. On the other hand, the pocket square is a fashion accessory meant to bring a pop of colour and pattern to the attire. Furthermore, it brings together different elements of the look.

If you find yourself offering your handkerchief to someone, do not expect it to be returned. Likewise, if you find yourself without a handkerchief and you need to use your pocket square for hygiene reasons, do not place it back in the display pocket.

When to Wear a Pocket Square

The easy answer to the question is: wear a pocket square every time you wear a blazer with an open breast pocket. However, wearing a pocket square is a matter of style.

Men's style can be like David Beckham's, who will mostly be seen attending events wearing a suit and pocket square. Or at the opposite spectrum, like George Clooney, that manages to get away without a pocket square even on red carpets and still tops the best-dressed list.

If your style is consistent, then one can wear a pocket square or not. But the emphasis is on consistency. On the other hand, if your brand is to indulge and use accessories, then pocket squares are your true friends.

Informal Events

When attending informal events, a man will usually forego the tie but not the pocket square. Instead, depending on the season, one might wear a scarf, or nothing, around the neck. In the world of men's dressing etiquette, unstructured jackets and blazers are appropriate to more casual events. But even those come with a breast pocket meant to house your pocket square.

A gentleman can pair his blazer with smart trousers, a tailored shirt, elegant shoes and a pocket square to bring together all the patterns, colours and textures.

For casual occasions, choose lightweight fabrics and fold your pocket square following the puff method. Learn more about what fabrics aid you to form the desired fold in our next article. If you prefer an easy-going look, just use the casual puff fold.

However, if you want to take it to the next level, master the rolled puff fold. The rolled puff is similar to the puff method but adds an extra step: the rolling inwards, which can require some practice

Formal Events

It goes without saying that when you attend a formal event, you will need to suit up, wear a tailored shirt, tie or bowtie, your best shoes and a pocket square. Depending on the event, you can sport either a multi-coloured pocket square or choose a unique and sophisticated fold.

The more classical folds for formal attire are the presidential fold, the TV, the one tip-up, the two points, the crown or the Windsor puff. These are beautiful folds and relatively easy to master. Use a linen or cotton pocket square for folds that require to lay flat and silk for puff folds.

If you are daring and choose a more complex fold, it can match the event's theme, such as the rose fold, the Christmas tree fold, the sail ship fold, the bird of paradise fold, the three petals fold, or the ice-cream fold just to mention a few.

Never Wear a Matching Set

When formal dressing is required, a big faux pas is wearing your tie and pocket square as a matching set. The two accessories should never be from the same fabric and print. The role of the pocket square is to complement and harmonise the look. In the next episode of the Pocket Squares mini-series, we explore the details of a high-quality pocket square and what to look for when shopping for such an accessory. Follow the #DHPocketSquares for beautiful accessories and styling tips for the modern gentleman.


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