I totally get what you mean about wanting a new outfit for every event or every time you go on vacation. I used to be like that too, especially when I was in high school and college. I can't remember exactly what changed, but it might have been when one of my college roommates complimented a shirt I was wearing one day, and asked if it was new - it happened to be one that I had worn a hundred times before and that she had definitely seen me in many times. I realized then just how little people were paying attention to what I was wearing, and that it was a waste of money to try to buy new clothes to impress them. Now I hardly ever buy new clothes, unless I really need to replace something that's worn out.