I think windows 95/98 era was the peak of UI discoverability. As a kid, I and my friends could learn and explore how a program worked just by expanding all the menus and opening the various dialogs. Dialogs which were filled with fields and their descriptions! Before then, it was the world of DOS and you had to know what you were doing ahead of time. And now, UIs are dynamic, initially hiding stuff from the user and…
Many dos programs with a gui had all the same menus and fields before Windows. They just ran one at a time.
Also for MS-DOS, the BRIEF editor for programmers used tiling windows and (optionally) a menu-driven interface that was better designed than that of most later text editors. It also allowed the redefinition of what happens when any key on the keyboard is pressed. The default action of inserting in the text the associated character could be replaced by an arbitrary script, which made easy the implementation of things like auto-completion or syntax coloring.
Nevertheless, even if some important applications in Windows 95 were still regressions from the point of the user interface in comparison with what was available for MS-DOS, Windows 95 looked much nicer than anything using the standard VGA text modes and it was the version to which I have switched from MS-DOS.
Even if I had previously tried Windows 3.0, 3.1 and 3.11, those had felt too much like useless toys, in comparison with the professional programs that I was using under MS-DOS. The Windows 95 taskbar was definitely a very important improvement over Windows 3.x.