I think Microsoft is actually gaining a bit of a "cool factor" with their Surface line of products. They're nice, and beautiful, and can do things Apple fans can only dream of with their Macs. But it'll be a long while before Microsoft is the "new Apple."
I would like to add that I think if any company can do it, it's Apple, and that I also think Apple is slowly losing that "Apple-ness" that other companies seek so hard. They're not the innovators anymore. Every year it's less about innovation and more about being the most powerful, which used to be how Windows OEM's did it. And it's like they're making changes just for the sake of changes. They've hit a wall with iOS's UI/UX design and now they're just moving things around and changing things for no real reason. I personally think the new design for the Control Center, notification center, and App Store are atrocious. Apple makes great products but lately it feels like they're coasting. Then you have Microsoft releasing things like the new Surface Pro and the Surface Studio, and working to build one operating system to rule them all with an adaptable and fluent UI design that marries consistency with beauty. Microsoft isn't there yet, but they're closing fast.
All that's left for Microsoft to do is actually transition from that "nerdy company" to a modern, open company that can properly communicate with their consumers and bring products to the whole world in a timely fashion. And for them to figure out what the fluff they're doing with Mobile.