I think the GP's point is that if one feels the need to use a status symbol, they're already pretending to be someone they aren't.
Of course a status symbol works to a large extent, otherwise people wouldn't be spending money on them.
I'm nowhere near the social circles of "old money", but I'd imagine they're more amused with seeing people trying too hard to push themselves into upper society, than being insecure about their own status. I mean, I don't have to be upper class to find this behavior somewhat comical.