When I was fresh out of college (about 20 years ago for context) I was shadowing an executive for a meeting with a bunch of people. I asked him if I should wear a suit and tie. He said you can’t go wrong in a suit and tie, but whatever you wear tells everyone in the room what you want them to think of you.

Some people dress comfortably because they don’t want to impress anyone. Others dress comfortably because they want you to think they don’t care if you’re impressed. And then there are people who dress comfortably because they don’t need to impress anyone.

I asked him what the difference was, and he said it’s the cost of the tie they aren’t wearing. I always thought that was clever while also completely useless.

Then in the meeting he made a bigoted joke and killed the entire deal. So, I don’t quote his advice often, but I thought it was relevant here.