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Alright I just figured out styling, and it has nothing to do with matching tags or colors.
Black > solid brown > brown with pattern > pink > blue
Basically it's about how stylish or costly each individual item is, not how good it looks. This is why I can wear mismatched colors and still get the "music notes" for my outfit, while an outfit made up of completely complimentary colors will get the normal rainbow stuff.
I don't know why I expected there to be more depth.