I'll be the first to say the unpopular take on HN: I don't think Windows 95 looks that good (compared to today). I personally find more modern (like MacOS 10) styles to look the best, and flat designs to be just as usable as more skeumorphic ones. It seems to me that preference for UI styles is completely personal, probably being influenced by what OS we initially used. As someone (potentially a lot) younger than man…
I agree that most of the preference is personal. I am not so sure on the age thing. I am likely on the old end of the curve here, yet mostly prefer the flat appearance. That said, there are a few elements of those old designs that I prefer. There are a few areas where those old interfaces shone: being able to distinguish between UI elements, higher contrast, consistency, and exposing functionality. That is to say: buttons don't need to be raised and links don't need to be underlined, but it is useful to know when you are looking at a button and a link.