I never really made use of Windows until 3.1 came out, but I remember looking at it and wishing it was actually more useful, rather than being a (very light) graphical overlay of DOS. I was a Mac guy back in those days (oh, my beloved SE/30), and until we hit Win95 I just didn't see much of a point in switching..
Reshared post from +Donald Mclaughlin

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I was one of those weird people who liked DOS better than 3.1, and I had no experience with prior iterations of Windows.
It feels weird to think about Windows 95 being so long ago, especially since that marked a major acceleration in development and convergence on a single platform. Right around that time (give or take a year or three) was the birth of the long-lived Pentium series, optical media for software, the first broadband connections and personal websites like Geocities.
I was very comfortable with DOS, even with it being single-threaded (though, in restrospect, juggling different memory types and dealing with print drivers was a real PitA).
Deskmate FTW!
All this has happened before. All this will happen again. http://www.geeksaresexy.net/2011/09/16/windows-1-0-vs-windows-8-pic/
I remember being super excited when I installed Windows 95. It really was a big leap in UI design at the time. It completely blew the Macs (System 7?) we had at school out of the water in terms of usability.
Windows 95 beat Mac System 7 for usability? I don’t think so. In my experience, Macintosh was significantly easier to use than Windows in that time period. Sure, a Windows power user could get as much done about as easily as a Mac power user, but for the average people I knew at the time when Windows 95 and Macintosh System 7 were competing, Macintosh was much easier to use.
I think Macintosh OSX has recently lost its way with respect to usability, and Windows has gotten much better (Windows 7 anyway, I haven’t used Windows 8 much yet). Now, I think the difference is much smaller, and it’s not clear which is easier to use. But back in about 1995-1996, my experience indicated that Macintosh was better for the average user.
Windows 95 beat Mac System 7 for usability? I don’t think so. In my experience, Macintosh was significantly easier to use than Windows in that time period. Sure, a Windows power user could get as much done about as easily as a Mac power user, but for the average people I knew at the time when Windows 95 and Macintosh System 7 were competing, Macintosh was much easier to use.
I think Macintosh OSX has recently lost its way with respect to usability, and Windows has gotten much better (Windows 7 anyway, I haven’t used Windows 8 much yet). Now, I think the difference is much smaller, and it’s not clear which is easier to use. But back in about 1995-1996, my experience indicated that Macintosh was better for the average user.