Up to Win2k, I don't recall new releases of Windows leading to people lamenting the UI changes; I do remember people not liking the initial look of XP, though. Maybe it's just because complaints got more visible after the Internet became popular, though. But even now few people seem to have strong preferences for, say, Windows 1.0 (… which was pretty much a TUI, IIRC)
I believe Win9x all had basically the same UI appearance, and 2k just changed the default colours slightly (and they were always fully customisable, so no difficulty in changing them either.)
Windows 1.x/2.x were noted for being rather primitive, and similar to the "flat design" trend hated by many when Win8 came out. 3.x is when the UI elements became 3D, and then they retained nearly the same appearance until XP introduced the bitmap-based theme.
IIRC win2k introduced some transparency effects and shadows, like when menus would gradually appear from transparent to fully opaque (I don't know the right word for that.) I found it really cool at the time.