‘Coolness is a subjective, positive trait perceived in people, brands, products, and trends that are autonomous in an appropriate way’

Basically this “means departing from norms that we consider unnecessary, illegitimate or repressive — but also doing so in ways that are bounded.”

Back in 1984, Apple achieved this by saying, in effect, “you have a choice; don’t buy IBM!” (link) This also worked because enough people saw IBM as “something worth rebelling against,” but not to the point of, say, violence.

Such iconoclasm can be applied in reverse, as did an anti-smoking ad campaign associating tobacco use with “idiot conformity,” which proved highly effective among teens.