If you are not used to wearing a pocket square you might feel a little sheepish about it. Get over it. It is a fantastic way to dress up a blue blazer or khaki sport coat and it totally makes you look pulled together. I felt a little weird when I started wearing them, like I was trying too hard, but very quickly I started to like the way I felt and I could tell from the reactions I was getting that it great! No one has ever said “hey, nice pocket square” (and it should be subtle enough that they shouldn’t) but just a “you look great” - when all did was a little piece of cotton in my pocket. Super cheap wardrobe makeover! A blazer with a pocket square, jeans and a pair of sneakers is the perfect summer look that can take you almost anyplace. We prefer a squared-off pocket square so it doesn’t look too worked. Gingham is always fresh and chic. Also, here is a great video that shows you how to fold them.