People buy and use products for a delightfully large and complex range of reasons. I have always been drawn to Macs because they have enabled me to do the work I use a computer for in a way that has suited me and my preferred way of working. Now, had the many Apple computers that I have used over the years not worked well or had been frustrating to use (and by this I mean for what I use a computer for, not necessarily what you use a computer for), I wouldn't have stuck with them. Could I have used a PC running Windows to accomplish everything I have done with my Macs? Absolutely. I just prefer the experience and stability of using a Mac. This doesn't make me an elitist, just a consumer with preferences. "Coolness" has nothing to do with it.
I don't care at all which computer people choose to use—they should use the hardware and software that best suits their needs, interests, temperaments, and budgets and we should all celebrate that there is at least some choice in this matter. Even if some consumers choose a product because of a perceived "cool" factor, so what? Let people decide for themselves. Some car buyers will choose a Kia, some a Ford, and some a BMW. Isn't it nice to have a choice?
What is tiresome about the new ad from Microsoft is 1) Microsoft already enjoys the largest share of the desktop OS market, and 2) the sneering implication that people who base consumer decisions on anything other than price are somehow elitist. Pretty ironic, coming from a company whose current and former executives are wealthy beyond understanding and often live like kings (unless you think that $147 million houses, mega-yachts, and space tourism are not, well, somewhat elitist themselves).
Microsoft, for all its strengths and weaknesses, seems unwilling to cede market share to anyone else. Their executives routinely spout the mantra of "Microsoft everywhere". This is the core of my long-standing distaste for them—they simply don't want to share. (To be fair, I have also long squirmed at Apple's "I'm a Mac/I'm a PC" ads as being too smug.)
What puzzles me is when a company that already enjoys a dominant market share takes a swipe at the rest of us who choose something else. I say having choices is a good thing.