I've seen many suits, often in a group, that are the most obnoxious people you'd ever meet. The sort of 'do you know who I am?' type. When I used to commute to Liverpool Street, these were almost certainly people who worked in the City of London, in a bank or were traders etc. If you saw them, you'd probably go seeking out a bunch of hoodies to sit with instead!
I saw a fair few that just used to pull out a tenner (as was the PF amount at the time) and try and pay the gripper as if it was some sort of tip to 'move along'.
And I've also seen very well dressed ladies, in their late 40s and 50s who could be incredibly foul mouthed and abusive to staff.
The thing is, I still think stereotyping still works. I bet you could quite accurately tell from body language, or simply how people talk to each other, as to what they'd be like in certain situations.
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When I last flew Virgin Upper Class, there were very few people in suits! In fact, if you're really important then I very much doubt you'd be dressed smart. A lot of people I've met (including Richard Branson, who I once worked for) certainly don't dress up, but have rather a lot more money than the suit who is travelling on company expenses anyway.
In a restaurant or certain hotels it is different, as there might actually be a dress code.
