Do I need to match my tie with my pocket square?
Firstly, let me commend you for even asking this question. It is sad to say, but most men today do not even give consideration to the purpose for which their outer breast pocket was created – many even leaving the stitching in place for their off-the-rack jackets.
But it is a real style question… With a white shirt, it is easy: white in either silk that is folded or scrunched or folded linen. With other shirt colours, you are given the challenge to choose a colour that compliments the tie and the shirt. Don’t match the tie and the pocket square – it’s just tacky. Some would say that you should use real handkerchiefs – so that when the damsel in distress cries out for your aid, you can give her a real handkerchief to wipe her eyes.
I don’t know whether I would want to do that, but it does make a great story. Experiment – overall, you get a lot of latitude for even trying!