Originally Posted by
Proudelitist
I tend to wear what I need to, and if I am coming from or going to a business meeting, then I will be in a suit.
However, I have found that wearing a suit tends to get you smoothly through other aspects of travel. It really makes no difference onboard the plane, however it DOES make a difference when dealing with staff and in unusual circumstances, be it GA's, hotel clerks, rental car agents etc. Right or wrong, if you exude authority, confidence and means, you tend to be treated better than if you are standing at the counter in jeans and a t-shirt.
None of this is necessary when you land in Hawaii. Nothing says I am the man like a nice high ranking status at a hotel (e.g. Diamond at Hilton) or Chairman at the airline counter. What you wear is less important than "Who" you are.