Updated: Jan 25, 2019
Perhaps you remember, like I do, when a retail employee attempted to sell you a pocket square and tie combo pack. We are gentlemen. We know better than this, and if you don't... you're about to!
First and foremost, your pocket square should never match the pattern of your tie. Often, the most stylish combinations of pocket square will have but a trace of the ties color in its design. However, if you are not the adventurous type make sure that if you're wearing a patterned tie and opt for pocket square of the same base color make sure the pocket square is either plain or subtly patterned.
Secondly, pocket squares should always be made of silk or linen. Don't you dare defile your fine wool suit with a high-sheen polyester pocket square. Silk pocket squares allow you to be as creative with the implementation as possible. Either look up tutorials on how to fold a pointed peek pattern or shove it in the pocket nonchalantly. Both will look sophisticated as long as the rest of your outfit is assembled with finesse. Linen pocket squares on the other hand should almost indiscriminately be worn in a presidential fold pattern. This is my go to fold. There is no situation in which this fold will be out of place, especially if your pocket square is white linen and you're wearing a white shirt.
Pocket squares are another means of conveying your confidence and style prowess to the world, embrace them. You will make mistakes and it will only become apparent to you in pictures afterwards but each failure will be but a lesson on this, your style journey.