If you read through old HIGs, they generally have actual concrete reasoning behind the choices they made. They're pretty interesting to read because back then they did scientific user studies to try to make computers more usable.
For example, Microsoft didn't make the UI gray because of some aesthetic preference. They chose gray because black-on-gray text is easy to read, and because it makes it immediately obvious what's UI vs. what's content (vs. if they made the background white or something). They made all the buttons three-dimensional because it makes it immediately obvious that something is clickable. Getting rid of stuff like this makes the UI prettier, but it also gets rid of hints for how to use the software.
[–] cowlevel 2 days ago
[–] rafram 2 days ago
macOS’s Apple menu, which only ever contains system management commands and doesn’t try to be an app launcher too, is so much more logical.
[–] ndiddy 2 days ago
Because of how much of a radical departure Windows 95 was from previous UI designs, and because of how driven the design was by user testing, there's a lot of information available going over why the design is the way it is. For example, there's an article going over the iterative design process here: https://socket3.wordpress.com/2018/02/03/designing-windows-9... and there's a detailed document explaining the UI for reviewers here: https://web.archive.org/web/20260209083725/https://tech-insi...
How do they know it's good design? Did they think long and hard about where people would click to shut down? Maybe, but the more direct reason is they had user testing labs, and at the end of the test they asked users to shut down the computer, and almost all of them clicked on Start.