It is best to play it safe. You can never go wrong with a suit. But if you are underdressed, it may work against you. These meetings are not the place to make a statement about life style. They are just meetings. As the saying goes: When in Rome, do as the Romans do.
I don't agree with that. A suit is not playing it safe, while say clean jeans and a nice shirt (not a t-shirt) is playing it safe, if you usually wear jeans and a t-shirt. I'm in the gaming industry and pitching with a suit would just be wrong, it would give a suck-up look. You don't believe in your company enough so you have to mask it by wearing a suit?
There is no correlation between wearing a suit and one's lack of self-esteem, trust to his company or whatever. Dressing up does not make you less confident (or more confident for that matter). By that logic, homeless people with shabby clothes must have the highest self esteem among all of us.
There is a proper attire for every social event. For example, if you go to the beach you are expected to wear a swimsuit while you are swimming. Wearing a suit while swimming would be ridiculous. Doctors are expected to wear a white apron in the presence of patients. It would be weird if they still wear the apron in bed. Similarly, if you are having a first time business meeting with anyone, the safest way to play it is to wear a suit. It is the universally accepted dress code for meetings. Then, depending on the personality of the people you are meeting with, you can dress down in the next meetings.
