I always buy exactly the same underwear - Fruit of the Loom boxer briefs "trunks". The trunks version have shorter legs and allow me to wear them with skinny jeans. I buy them in the Black/Grey pack which has 3 of each color so all my underwear are exactly the same and in only 2 colors.

DAE do something like this? I find it works perfectly for the way my brain works. I also only buy the exact same socks (excluding my dress socks). I buy 1 version of long socks for the winter and a version of shorter socks for the summer so that anytime i pick out socks I never have to worry about "matching" them up. It is either a long or a short sock. Makes things easier.