I wonder if all that just comes naturally to them or it feels like the "prison" it seems to me as an outsider. Constantly caring about this stuff, buying new clothes, looking out for fashion trends etc seems exhausting. I'm the typical nerdy wrinkly T-shirt and jeans guy and I know I'll not get into high circles anyway, and subjectively it feels quite freeing not to care. I spend my time immersing in stuff I'm actually interested in, not any required stuff like watches and suits and fine wines and whatever else. Or perhaps to these people it's not a burden, they naturally care about watches and fine wine... I honestly have no idea but would love to once speak honestly about such things with insiders...
Edit: upon some reflection, perhaps my stereotypes are outdated and it's not really necessary for even old-money-rich young people to care about fancy watches and wines any more. I mean some base level knowledge is needed, but I have to remind myself that when I think they may have it worse in some respects I'm probably wrong. Why would they restrict themselves to rigid bullshit, if it's not pleasant? Probably the rules are more flexible today. Probably I'm totally blind to whatever the current actual class markers are as they are invisible to us.
The point is that these people don't care about fashion or watches or how much you spend on your clothes. They dress conventionally instead, which is a standard that only changes over the scale of a decade or so. The mistake outsiders make is to think that the point is to follow fashion and buy an expensive watch. That's why they don't fit in - they wear something fashionable.
Also, to defend the idea a bit, the idea of a dress code is exactly that purpose - so that you don't need to worry about what you're wearing or how much it cost or wether someone thinks it's fashionable or not.
I always come back to the cinema image of the rich guy casually tossing the keys of his supercar to the valet. The reason it's "cool" is the effortless balance. He has fun with the car, but he is no petrol-head. To you & I it's an unobtainable thing, to him it's just another car.
That's how I've come to understand it. These wealthy types are not horophiles or sommeliers. They just casually appreciate beautiful craftsmanship & the taste of high quality alcohol- and who doesn't? Just look at how techies love machined metal laptop bodies, and the popularity of craft beer. The reason out-groups are quickly identified is because they cargo-cult the material things.
Edit: upon some reflection, perhaps my stereotypes are outdated and it's not really necessary for even old-money-rich young people to care about fancy watches and wines any more. I mean some base level knowledge is needed, but I have to remind myself that when I think they may have it worse in some respects I'm probably wrong. Why would they restrict themselves to rigid bullshit, if it's not pleasant? Probably the rules are more flexible today. Probably I'm totally blind to whatever the current actual class markers are as they are invisible to us.