in: Accessories, Featured, Style

• Last updated: January 12, 2024

How To Properly Rock A Pocket Square

Gary Cooper giving pose in suit illustration.

For the past four decades, if American men regarded the breast pocket on their suit at all, it was as an extra place to store sunglasses or business cards. Some men don’t even undo the stitching in the pocket that comes with a new suit.

However, men are once again rediscovering the art of sporting a pocket square. Peyton Manning rocks a pocket square with his suit, as well as George Clooney and Diddy. Hell, even Saddam Hussein rocked a pocket square when he was on trial–a man should never defend his war crimes without one.

The pocket square is a small accessory that when added to an outfit, allows men to express themselves and vary their look without having to buy a whole bunch of different suits. It can add a bit of interest to your appearance without it looking like you’re trying t0o hard.

The History of the Pocket Square

The origin of the pocket square goes all the way back to the ancient Greeks. Wealthy Greeks carried around perfumed hankies as early as 500 B.C. English and French noblemen carried perfumed and embroidered hankies in order to cover their noses from the stench of the streets and other people.

In the early 1900’s, a dapper gentleman would never leave the house without a pocket square tucked neatly into his suit’s breast pocket. Yet by the latter half of that century, the pocket square began to go the way of the hat. It’s high time we bring both back.

Pocket Square Guidelines

Don’t leave your suit naked. Trent Bridges, a friend of mine at law school, refers to suits without pocket squares as “naked suits.” He argues that a suit just doesn’t look complete without one. I agree. The addition of a pocket square adds some finishing panache to a good suit. So, the first guideline of pocket square usage is to always wear one when you wear a suit or sport coat. It just looks better.

Color co-ordinating. A pocket square can be patterned or solid. The general guideline is that your pocket square color should compliment some color on your tie. So, if your tie has a bit of red, rock a solid red pocket square or a patterned pocket square with some red in it. However, avoid matching the colors exactly. It looks like you’re trying too hard (so never ever buy a tie/pocket square set at your local department store). A white pocket square can be worn with any color tie, making this color handkerchief an essential part of every man’s collection.

How to fold a pocket square

You have several options on how to fold your pocket square. Some are super simple and others are complex. It all comes down to personal taste. In this post, we’ll discuss three simple folds that every man should master. I’m proud to present the Art of Manliness’ very first video which features my ugly mug demonstrating how to fold them. Below, you’ll find written directions.

The Straight Fold

Pocket straight fold.

The Straight Fold is the most simple of the pocket square folds. What you’ll end up with is a small rectangle peeking out of your suit pocket. Here’s one way how to fold it:

  1. Lay your pocket square flat.
  2. Bring the left side to right side
  3. Bring the bottom towards the top, but don’t fold it all the way.
  4. Fold the fabric in thirds horizontally so that it will fit your suit pocket.

The One Corner Fold

Pocket square one corner fold.

With the one corner fold, you’ll have a small peak of fabric coming out your pocket. This one is probably my favorite of the three. Here’s how to fold it:

  1. Lay your pocket square on a flat surface, with one corner facing up and one corner facing down so it looks like you have a baseball diamond in front of you.
  2. Bring the bottom point to the top point so that you create a triangle.
  3. Bring the left corner of the triangle to the right corner, and the right corner to the left corner. You should end up with a long rectangle with a point at the top. It looks sort of like a fence slat.
  4. Fold the bottom towards the top, but not all the way.
  5. Place it in your suit. Adjust until you get the desired amount of point coming out of the pocket.

The Puff Fold

Pocket square puff fold.

The Puff Fold is probably the simplest of the folds. The desired result is to have a small puff of fabric coming out your suit pocket. Here’s how to fold it.

  1. Lay the pocket square flat.
  2. Pinch the middle of the fabric, allowing the folds to come in naturally.
  3. With one hand firmly holding the pocket square, use your other hand to gently gather it together.
  4. Now gracefully gather up the bottom of the pocket square.
  5. Place it in your suit. Fiddle with it until you get the desired puffiness.

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