HOW DO I FOLD A POCKET SQUARE? -- MINE ALWAYS ENDS UP LOOKING LIKE A WADDED-UP PAPER TOWEL. Just keep folding it 90 degrees until it’s the right size to fit in the pocket and doesn’t have irregular corners, and when you’re finished, press down hard (or lightly iron it if there’s one handy). Then tuck it into the jacket pocket, making sure not too much is showing so it doesn’t look exaggerated. And it’s OK if it looks perfectly imperfect, like you didn’t try too hard.
How to fold a pocket square by Belisi -- If you haven’t heard, men's pocket squares are all the rage. Think Fred Astaire meets the 21st century (without the top hat). Sounds cool, right? Now’s the hard part: how in the world do you fold a pocket square?