I had the first Macintosh and thought it was VERY cool, and so did everyone else. When was Apple NOT considered cool?
Shortly after Windows 95.
I would say in between the mid 90s to the mid 2000s. It was like a counter-culture thing to use Macs/Apple products. Macs had a stigma about them, they were considered weird or odd, especially when talking to other tech people.
Other than the people I talked into getting Macs (family, some friends), hardly anyone else would use them. I would tell people that I used Macs, and sometimes I would get laughs.
I am not saying that the people that were not interested in Apple products had rational reasons for it, and many of the reasons were just plain dumb.
In my experience, the perception of Apple product becoming cool changed about the time that Macs switched in Intel. People might point out the iPod, but even with that, Macs still had that stigma about them. By the time that the iPhone and iPad were a success, Apple products, including Macs seemed to have lost the stigma it once had.