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Again it's the assumption that more expensive = more properly made product.
Think of it like this, possessions/things are valued to you in how much utility you can get out of them relative to your income.
Say, if you make $12,000 a year, a $100 Christmas dinner for 2 will seem like a big deal. You would not necessarily want to buy the $100 of wine because it won't taste 5 times better than the $20 bottle of wine.
However, if you up the scale to say $100,000 annually, at this point, buying a cheap nasty burger for $3.50 or whatever at McDonald's seems kind of a waste of your health, especially since you can easily blow $50 a day on food and not blink much. While you can stomach and drink a $20 bottle of wine it feels a little cheap to you and the difference between that and the $50 is small enough in cash that you'll prefer the flavor. You might stretch but go for the $100 knowing that it's not really twice as good as the $50 but decent enough, and within your budget.
As you say though, people who grew up in priviledge, and especially those who have no identity besides their wealth/power, and no respect for others or themselves, those are the people who give the well off a bad name.
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