Apple was never cool to anyone whose opinion I care about. I hated that smug hipster doofus on the "I'm a Mac" commercials, and I have to say that it fit quite well what I already thought of Apple and its typical users. It's so contrived and deliberate, which is the opposite of cool. Trying to be cool is not cool.
Microsoft's attempt to be Apple is even worse. Pretending to be cool is bad enough, but pretending to be someone else pretending to be cool just adds a whole other layer of stupidity. Microsoft was more cool when it knew what it was, and when everyone else did, too, including the makers of that same series of TV commercials I already mentioned. Now that they're trying to be Apple, or whatever it is they're trying to do, they're the farthest thing from cool.
Microsoft, try making a decent consumer product and then worry about the useless faff like being cool. Cool is the icing on the cake, but you don't even have a cake. Cool is in the consumer sector, and you're not going to get there with Azure. Not releasing garbage like Windows 10 and forcing consumers to beta test it themselves would be cool. Actually testing the software in-house to make sure it works is cool. The perception of Apple as "cool" hinges on its "just works" reputation at the consumer level, and here you are using consumers as cannon fodder for your corporate customers, then trying to compete with Apple by having your very own version of the Apple store. You're trying to apply the icing to a cake made out of nothing!
There has to be a kernel of truth in the perception that your consumer product actually does what it says on the tin (in Apple's case, that it "just works") before you can be perceived as cool. What exactly is it that makes you cool, Microsoft? What product do you have that's cool in some way? Did you think that copying the "store" idea was going to be enough? Apple was "cool" before there was ever an Apple store.