That is the question that Robin Hanson ponders after considering Geoffrey Miller's recent book Spent. Miller's argument is that we should shift from positional purchases to purchases that are more instrumentally valuable and/or more reflect our individualistic style. In reading his argument and Robin Hanson's selective but thorough debunking, I am reminded of Tyler Cowen's thesis about modern art that "we do in fact need some means of determining which of the rich people are the cool ones, and the art market surely serves that end." To me, there is nothing wrong with certain people spending lots of money on positional items. In fact, their actions are what allows Miller to signal his own uniqueness by shopping at thrift stores.
Let's assume that there is an equilibrium of personality traits in a population, such that if everybody is shy it is socially advantageous to be outgoing but if everybody is outgoing it is advantageous to be shy. Everyone recognizes that the equilibrium is unlikely to reach the optimal distribution at any one time in any one place, so people might speculate that others should display more or less of various traits. The weird thing is that your average social evangelist, such as Miller, has a tendency to argue for other people to act more like himself, when from a theoretical perspective they should be arguing for people to act less like himself so that his actions will be more valued in the personality marketplace. The reason for this discrepancy seems to be that they don't actually want people to act in the same way that they are acting, but merely for their own actions to become more socially valued.
Thanks to Tyson for stimulating a conversation about this idea.