Second that. We often try to reduce observations to little things we can understand and rationalize away. I think you know better than anyone that you can see people in China, for example, walking around in all sorts of clothing. And if one must group clothing styles you probably can confirm that you will find any sort of people in any group, rich people dressed in some lousy clothes, poor people borrowing to the hilt to pretend to have. Rich people dressing in expensive clothing, poor people wearing shit. And anything in between. Life is more complex and often times it is difficult or at least wrong to reduce people to categories. We must summarize to talk statistics but otherwise such summaries or stereotypes tend to lead astray.
Jobs and Zuckerberg harbour a rather standard nerd look, dress preference depends on the scene again, go to good districts in London, Paris, Geneva and most posh holiday resorts in those area( at east Switzerland and France, which i know better) and most folks don't dress cheap.
What's true is most luxury brands have at least 2 collections, with the cheaper lines showing big logos, and the posher line beeing much more discreete, at least logowise, while beeing more expensive, which I suspect makes it less obvious those are high end clothes to those not familiar.