Cool is no longer possible. McLuhan remark that in 1/2 a generation "cool" went from a claim of detachment and uninvolvement to claims of deep attachment and intense involvement, but the expressive form never changed.
Craighazen's point can be read that now cool is purely nostalgic.
The Picasso thing never worked for me, but it did effectively signal to me the idea that Apple wanted to connect its computer products to "cultured" lifestyles, where at the time curating one's life still has some meaning in terms of expansive cultural experiences, art, science+technology and wealth; wealth as a privilege that could be generated, not just inherited.
The Picasso branding was culturally honest even as Apple was effectively raping the ghost of Che Guevara to make itself recognizable.
Happily Apple told us about themselves in 1984 with Ridley Scott commercial: it's same thing with Google "Don't Be Evil" A good grift let's the mark in on the game... Or to put it another way "a leopard can see it's own spots"
I have no patience for any of the branding: "those magazines wind up in the trash" Once you are aware of a certain amount of manipulation by glamour, you begin to see all the best marketing is manipulating you with glamour... And after exposure to a lot of it, glamour always looks fake because it's about the systematic rejection of the actual world in favor of a more attractive fantasy world.
Moreover, marketing design is captive to the industrial moment of its production. Is Apple's iconography from the time of vintage-Mac really different from Microsoft's? No! Partly because the same designer did both regimes; she contracted for MSFT after Apple. But moreso because the design language was defined by the idea of bit-blat and the creative environments that were inherently pointillist. Why? Because that's how the engineers figured out how to make TV work, and the PC is a TV with an epically more fungible channel-changer.
McLuhan: The last person to tell you about water will be a fish.
That's where we are with boring Apple. At least in old timey dayz, all the engineering seemed fresh, but that was because so much seemed impossible until you saw it.
Now that anything's possible, everything gets boring.