I ended up briefing some very senior leadership…in a hoody.
I brief that specific group on a regular basis and it’s usually fairly laid back but this particular meeting a new, very high profile person was attending to get up to speed. Apparently everyone knew but me because they were suited up and all of the ladies were wearing makeup and had their hair all nice. And there I was, the lead brief, in my hoody and jeans and scruffy beard.
After the meeting I realized that it probably worked in my favor. Some sort of psychological “this guy must be really good because he dgaf about dressing to impress”.
Plus I think their is exactly as you said a stereotype that the better you are at your IT stuff the less put together you have to be.