I don’t think it necessitates disinvestment so much as a subdued and controlled persona. A cool person is someone, like Obama (as some one else mentioned), who does not present oneself as excited, anxious, confused, etc. There is a stoic connotation, that one must be cool, must excise the passions, to be in control. I could imagine Bordo arguing along these lines. So perhaps the cool person is disinvested from what other people think, not necessarily from the people themselves.

But then again, some of the cool people look pissed-off, like the rebel without a cause. Guys will often say “that’s so cool” when something blows up–especially if some one walks away from the accident without any injury. I’ve noticed that a lot of the favorite characters in movies and television shows (especially male characters) seem to be people we’d absolutely hate or laugh at in real life. So you also have the paradox that those who are cool in fantasy are a-holes in real life. Perhaps people are “cool” to the extent that they fulfill some role or persona that we wish we could have, that we could be so in control and indifferent to the dangers and social pressures against us.

Of course, not everyone can do this, because the development part is nerdy, and decidedly uncool. I guess it’s a bit like the uncanny valley, in that your coolness gets worse before it reaches a certain point.

The basic point probably comes down to doing something you love, and mastering it. Of course, I view coolness as the sort of person you’d want to befriend and hang out with, so these standoffish people don’t fit that mold.

So, you asked:

What does it mean to live in a society that defines “cool” as disinvested in other people and the social world?

Maybe Obama has changed that to some degree, for some people. I think his coolness was a big attraction for a lot of people, especially younger ones (even if cool isn’t necessarily a word they’d use for it). Maybe he’s shifted, at least temporarily, the definition of cool, from disinvestment in other people and society toward investment. Maybe. There’s always “hope,” eh?

Of course, I stopped caring about “cool” people when I got to college. Maybe that makes me cool, too?

Anyway, these are all images of anonymous models (except for the women on the actual magazine covers). I think cool movie stars are also well-known for being engaged — surely Angelina Jolie is cool, and she is known for her humanitarian work.