I have 4 teenagers in 4 different schools, and I also did some graduate university-level course work, and I can tell you that Apple products are "cool", much the same way Nike or Jordans are in the shoe realm. This was not the case 10 years ago, at least not like it is today.
It is an issue of perception, regardless of how many people own the product. Apple understands the product doesn't make you cool, the product is cool.
My point regarding the aesthetics is not to imply that it is the same thing as "coolness".
What I contend is that Apple is using aesthetics to up the "cool" factor in their devices, while ignoring actual functionality. Example: The Mac Pro. Or better yet, the Retina Macbook. They need to GTFOOH with that BS; it doesn't get any more obvious than that:
It's got only one port buuuuut... it's available in GOOOOLD!! The keys don't feel too good to type on buuuuut.... it's so THIN. You need (to pay more for) a dongle to charge and plug something in buuuuuut...it so LIGHT!! It's marginally lighter, much less powerful, and significantly more expensive than a MacBook Air buuuuuut....it's got a PRETTIER screen!! OK, I admit that one's a bit of a stretch but I see that as an artificial differentiator...done on purpose. There is no reason the Air is not retina by now other than that.
Now I somewhat agree that Apple may not go out of style, but this is because their marketing team is the BEST THERE IS, not because of their products' attributes.
And that's the point:
Apple has actually become a company that was really great at marketing their insanely great products to one that is FORMIDABLE at marketing.
So great is Apple's marketing team that their competitors purposefully make their own products inferior than their previous models in order to catch some "Apple coolness" (see Samsung's Galaxy Note 4 to Note 5 differences...you can do much less with the 5). But they're also available in GOOOOOLD. Unbelievable.
That is what Apple's focus is on now, keeping the products looking good, so that Apple stays "cool".
For my part, I hope they get back to building the BEST machines they can, not just the "coolest".