Wearing The Square
Still the most common question I hear- "How do I wear a pocket square?" But, considering the ways to put it in, really people should be asking "How should I NOT be wearing a pocket square?"
Most guys seem to struggle with it, folding it over and over and never getting it to look right. However in reality- there are more ways to do it right than wrong. Don't over think it, that is the main thing. Once you start staring at something, it never looks right even though it's perfect. It's like when you spell a word, and the more you look at it, the weirder the spelling looks- but you know it's correct.
What are the wrong ways to wear a pocket square? Showing too much or too little. You don't want it overflowing out of your pocket, usually you don't show more than an inch and a half. If you see someone showing more than that online, it's just for the picture (I hope). Also, make sure when you stick it in, it spreads the full width of the pocket. Other than this, however you put it in will most likely be fine.
The more and more you dabble with one, you will realize you can literally pick it up in the dark and stuff it in- and it will end up looking great. If you want to fold it, fold it. If you want to randomly stuff it, randomly stuff it. That finishing touch is all up to you.
Here are a few examples:
Tip: Silk pocket squares are hard to keep in your pocket, they always want to fall down or fall out. I personally never wear a silk one, always cotton or linen (or some blend of the sort). The thicker less silky fabric holds its position in the pocket, almost like the fabric latches itself onto the inside of the pocket.