I'd argue this change never occurred because "using Apple products" never "made you look good". And they don't make you look cool either.
That's just the perception some Apple users wanted in the 90s and that others want today. But it wasn't true then and it's not true now.
Depends on how you define it. I define "Using Apple products made me look good" in the sense that I easily got professional looking results done without going through unreasonable time and effort.
For example, to burn a custom DVD with a slideshow of photos, with Ken Burns effect and music, and a matching themed menu. Exactly what iDVD was built for, and iPhoto and iTunes integrated into this fairly seamlessly. You could put together such a DVD in a few minutes of effort, and the tools necessary to do it were included free with every Mac. I made and sold these for years, and frequently got compliments.
Could I have done the same with a PC? Sure, but it would have cost me hundreds of dollars in DVD authoring and video editing tools, and the results still would not have had the same fit-and-finish as the results from iDVD. (And I'm not just talking about warm fuzzy feelings, but quantifiable touches such as the menu fading out and the video fading in, little details that Apple programmers were careful about, but were absent in most PC software packages.)
I remember once making a Keynote presentation to a group. I never once "flaunted" the fact that it was not PowerPoint, or that I was not using a PC. Yet, at the end, people came up to me and kept asking HOW did I make my presentation so much more professional looking than they'd ever seen. Again, technically attributable to small quantifiable touches like smoothly fading slide transitions, well-designed templates (and granted, probably some points for not using the same-old templates everyone is used to seeing in PPT) or anti-aliasing around photo clip art. End result: made me look good as a presenter.
Or other little things like being able to pop open my PowerBook/MacBook, connect to the local network, and get working, while my PC friends were still waiting for Windows to boot/reboot/wake up, and fiddling with network settings. Or my laptop battery lasting 5 hours when typical PC laptops only lasted 2. The field has become much more even these days, but again I speak from experience, at hotel conferences etc. I simply got my work done faster and with less hassle than I did when I had a PC. I never looked at my Apple stuff as a status symbol, but I definitely appreciated the productivity boost.
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