> There's also a kind of signaling by people who are rich enough not to care about these things and dress accordingly, which is a way of reminding other people that you have so much money you don't care about what impression you make. This only works when people already know you're wealthy, though.
Fussell notes this in his Class. The group he categorizes as "top out-of-sight" (mostly old money) is genuinely beyond caring about appearances and are where you get a lot of "eccentric" rich-person behavior like wearing really cheap clothes. Upper-class folks, especially younger ones, may very carefully and deliberately dress way down, especially when traveling (for some reason), though they will not, and will not intend to, actually blend in.
Separately but somewhat relatedly, he claims that higher classes will tend to buy unexceptional things where spending more is seen as primarily a status signaling thing, and especially when the thing is in any way technological—so buying a flashy, expensive, new car belongs to the sensibilities of the upper-middle classes and lower (regardless of their income—talking about socialized class, not income) while the comfortably rich might just own a beat-up Chevy, or an old luxury car.
Where you do not see people do it is when there's a risk they might actually be mistaken for belonging to any part of Fussell's "prole" category—so, upper-middle and, especially, middle.