This is why, when you're rich, you don't want to look rich. In my experience, the very rich guy would look like the gentleman on the left. The guy in the suit, the guy being entrepreneurial, is the one pinching pennies
I remember our ceo would come to do our all hands meetings and he always dressed casually but you could just tell by the fit of his clothes he probably got them from somewhere with a tailor. So while the clothes looked normal the fit just stood out to me and made him look well off
Unrelated to anything else, but as someone that likes to thrift clothing, I highly encourage you to find a good local tailor. It's surprisingly cheap and, as you've apparently noticed, it makes a subtle but impressive difference in the clothes you wear.