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.
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.