On the other hand, I think there were few ideas worse than "My Computer", etc., not the least of which is the fact that it took Windows application software about 10 years to get consistently good at handling paths with spaces in their names.
Of course, the worst UI thing Microsoft ever did was hiding file extensions by default. That might be the worst UI decision in all of history.
The Windows 8 touch-first start menu with a hot corner instead of a button, applied to their Server OS, that I assume most accessed through RDP was pretty horrific.
When Windows 95 first came out, they had to have a giant arrow pointing to the Start menu with an explanation of what that would do: https://a.imagem.app/Ge6OCZ.jpeg
Then they had a scrolling animation with an arrow and some text ("Click the Start button to begin") that slid in from the right side of the taskbar and pointed right at the Start button.
The first computer I used had Windows 3.1, but I never really knew how to use it. I just played some games on it and my dad would have me feed in a stack of floppy disks for him when he had to install something big.
Windows 95 was the first OS I used and explored on my own and made sense to me.