This list is not in order of importance 1) Strangers you want to have conversations with. 2) People you already regularly see. 3) People you want to attract or significant others you already have. 4) Comfort and your own enjoyment. 5) You can also anti-optimize your clothing to filter out people you don't want to interact with. 6) People who you want to hire you. 7) People you are trying to sell things to.

It's also important to remember that you can wear different clothing at different times. In some of these cases, especially salesmanship, optimizing your clothing will be very similar to optimizing it for the vast majority of people. But the point is optimizing for the majority isn't a good thing in and of itself, it's a path to an end.