The Right Way to Wear a Pocket Square

Well-dressed man wearing a jacket with a pocket square

Well-dressed man wearing a jacket with a pocket square | iStock.com

Pocket squares demonstrate a man’s self confidence, as well as an astuteness in all matters of personal style. The man that dons a pocket square is at the apex of sophistication, in no way shy, and a true gentleman through and through. If you aspire to be at the pinnacle of personal style and sophistication of dress, then no excuse is acceptable. Donning a pocket square is also an easy way to boost your outfit in less than five minutes.

Before we get into how to actually wear the pocket square, here is a little historical perspective on this menswear fashion statement, from Egyptian handkerchiefs to modern pocket squares. First appearing in Ancient Egypt around 2,000 BCE, wealthy Egyptians were thought to carry the first true pocket squares that were made of bleached white linen. Fast forward to the 1900s, when no fashionable man left home without a pocket square made of silk, linen, or cotton in his suit jacket’s left breast pocket. It was for only a brief time in the 1960s that pocket squares were a little less popular, but they have since risen again to the ranks of high fashion, as well as casual street fashion.

Two men dressed in suits

Two men dressed in suits | Brooksbrothers.com

Generally speaking, a pocket square is meant to complement a man’s shirt or tie, and it should rarely, if ever, directly match it. If you choose to go that route though, match it to a minor or secondary color in your tie, shirt, or jacket.

While white pocket squares of linen, cotton, and silk are always on point, the confident man tends to wear silk pocket squares with elegant woven patterns or beautiful prints. Traditionally speaking, they are folded with a point and are usually pointed away from the heart. An older rule to adhere to says that you should not have your pocket square show more than an inch and a half above the pocket, but today, those rules are tossed out the door.

The first thing to consider is texture. For example, a smooth satin silk tie can be contrasted with a linen or handwoven silk pocket square. Modern pocket squares are usually 10 to 18 inches lengthwise and are generally made from a few types of fabric. Pocket squares made of smooth textures such as satin or silk are generally best if the square itself is a little larger because they have a tendency to fall into the pocket and bunch up. On the other hand, rougher textures such as linens and handwoven silk can do very well with medium-sized pocket squares.

When to wear a pocket square

Man in a suit with a pocket square

Man in a suit with a pocket square | iStock.com

You’re probably wondering when you should rock the beloved and versatile pocket square. Men’s Fashion suggests wearing it for these occasions:

  • If you’re serious about rocking this trend, then you should wear it every time you put on a blazer or a suit jacket.
  • If you’re going to a formal event or will be in a formal setting where you have to wear a suit, consider amping up your suit with a pocket square to stand out.
  • If you’re going for a more street casual look (even if you’re wearing chinos or jeans) but you’re wearing a cool blazer, try a pocket square. Also, nix the tie.

There you go, gentlemen. A definitive guide on to how to wear and rock the pocket square. You’re probably wondering about the most significant and important aspect to wearing the pocket square itself: learning how to fold it. We’ve got you covered. Try this Art of Manliness illustrated step-by-step guide to actually setting up the pocket square. Now, you’re all set to go.

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