How do you proceed to make a decision in the morning?
I have close to 2,100 pairs. Of those, many are in permanent display cases around my house and the precious metals and gem ones are kept offsite in a secure location. That leaves "only" 300-400 pairs to choose from. I pick mainly based on color of the shirt and tie I am wearing. A lot of times I wear the least expected one, such as the nut and bolt pair. I love the contrast between a bespoke DB chalk stripe suit, spread collar, perfectly placed dimple in my tie, linen pocket square, and a fun pair of cufflinks. To me, it shows you have a sense of humor. It also, IMHO, shows that you know the rules well enough to know how to subtly break them.