If the actually rich people are dressing down-to-earth, why would you dress fancily to appear rich? Surely you want to also dress down-to-earth so you appear like the rich people do.
Because if are a nobody and noone recognizes your face people will heuristically assume you aren't a "down to earth billionaire", but are instead just a poor, average person and thus insignificant. Zuck can appear to be humble in his clothes, because everyone knows who Zuck is and people expect famous billionaires to be smug assholes, so this is a way to countersignal and pretend to be "just like one of you, guys". Since you are "just one of us", it's in your interest to appear as something more.
You may not be mistaken as a famous tech billionaire, but you may be mistaken as a well-to-do tech worker or even a tech startup lottery winner.
An example of this is in luxury retail stores, fancy/business clothing used to be such a strong signal of high status that retail workers there would often ignore you if you walked in wearing T-shirt & jeans because they'd think you couldn't afford it. Nowadays, that's a lot less likely, they know too many people dress like this for a retail worker to safely assume anything. There are a lot of wealthy people who aren't in the news all the time and a lot of them don't dress like a traditionally wealthy person.
"Higher EV in that play allowing increased chances to mingle with rich class" means that your intended audience is the actually rich people because you want to mingle with them.
I stand corrected; in that case I'd wholeheartedly agree. Do you have any concrete instances of when/where one might do this? (I'm having a failure of imagination, because IMX in capitalist countries people dress to impress their peers; the system is self-sorting as in Brave New World)
A techy scenario I just made up: you're in a common space (eg a bar, gym, or conference) in San Francisco where rich venture capitalists tend to visit, so you dress like they do to fit in. Your goal isn't exactly to portray yourself as rich, but you want to portray yourself as a certain class: not necessarily a millionaire but someone who is doing well and has industry experience & connections and looks like they could lead a successful startup.
One approach is to dress like other famous & successful tech founders: a nice T-shirt & hoodie. T-shirt & hoodie is also just comfortable and common, which is exactly why those famous & successful founders wear it, they're not showing off traditionally by wearing $10,000 tailored suits, they're wearing a T-shirt & hoodie that anyone could wear. Dressing up with a fancy suit might actually look odd amongst the Silicon Valley upper class.
Edit: Another interesting example I thought of when replying to another comment is in luxury retail stores, fancy/business clothing used to be such a strong signal of high status that retail workers there would often ignore you if you walked in wearing T-shirt & jeans because they'd think you couldn't afford it. Nowadays, that's a lot less likely, they know too many people dress like this for a retail worker to safely assume anything. There are a lot of wealthy people who aren't in the news all the time and a lot of them don't dress like a traditionally wealthy person.
