OP isn't trying to just dress nicely, (s)he's trying to be the best dressed. If you were competing on looks, as OP suggests they are, and you were attempting to

OP isn't trying to just dress nicely, (s)he's trying to be the best dressed. If you were competing on looks, as OP suggests they are, and you were attempting to be the Most Casually Dressed person, or something like that, then I would be interested to know what happens when you met a more attractive version of yourself, too. When your goal is vanity, but you're outdone by nature, what happens to you in your mind? Just curious. The business card scene in American Psycho comes to mind.