Interesting post, fxh. You're right that clothes always send a message, and we need to be aware what message we are sending with our choice of outfit.
In my previous post I claimed that I only dress to impress myself, no-one else. That's probably not entirely true. I guess what I meant is that I want my message to be subtle, subliminal.
Not "Wow, that guy is a real dandy".
But "Wow, that guy really has his shit together" - not even realising that it's partly the clothes signalling this message.
Especially in work situations, the people one interacts with should not overtly notice one's outfit, except maybe later on, to think to themselves "...and he was nicely dressed too".
There are exceptions, of course. If you're actually in the clothing/textile industry, your own clothes should be noticed. Our Henry Carter guy (I forget his real name) dresses impeccably but doesn't overdo it. He is actually framing his core product the way a haircut frames a face. He's also demonstrating a possible context for the client's own potential use of that product.
In other fields (including my own), dressing a certain way can signal a level of success, which in turn builds trust for the client. "This guy looks successful, he must be good at what he does." Again, not quite consciously aware that the clothes are influencing their impression.
Not "Dress for Success". More like "Dressed through Success".
Then again, context context context. A younger guy can get away with a look which signals "This is where I am heading...this is the person I want to be in the very near future". We can forgive him this hubris because he's young, and we instinctively like people who are on an upward trajectory. I'm older and there's no excuse for me to be wearing shabby clothes and simply not caring. I should know better by now. Hopefully I do.