This is An Art—Not a Science Theres no steadfast rule for choosing a pocket square. It should simply complement your shirt and tie, not match them. If it looks right and feels right, walk out the door. Bandana Pocket square, $3 by KSI NYC. Sports jacket, $329 by Club Monaco. Shirt, $350 by Todd Snyder. Tie, $15, and tie bar (throughout), $15, by The Tie Bar.