The clothes you wear communicate. They communicate to other people before you say a word. So what are you saying when you dress like Old Money?
You’re saying that you’ve placed your priorities elsewhere: you’re not following the latest trend; you’re not spending your money on clothing that will look silly in a year, and may even look silly now.
You’re implying that you take the long view: you’re an investor, rather than a consumer, and as such you look to buy things that hold their value over time, which quality traditional clothing does.
You’re inviting others to assess you, not your appearance: you don’t dress to call attention to yourself, and in doing so you may attract a more welcome kind of attention, namely interest.
You’re conveying the idea that you’re unafraid of being considered a “conformist”: everyone conforms to something, and there are worse things that conforming to the values, priorities and habits of Old Money.
So when you dress, watch what you say.