I think this is a life skill which you've developed already but aren't thinking of as the same thing. The stereotypical example: your mother looks terrible in a dress but really loves it and she doesn't need to impress anyone, so you might say she looks good anyway. That's just one point in an extremely wide spectrum the issue encloses, in which you probably have feelings already on what's best when. I think the decisions are personal, dependent on the situation, and often hotly debated.