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To me, XP and Vista looked like a terrible attempt at replicating Mac OS X when that all wow'ed us - it's hard to imagine these days just how big of a deal the iMac and later on OS X were in terms of moving away from grey boxes everywhere (though sometimes too far, since Windows 7 really toned down and refined XP/Vista's UI).

For me, I grew up on Amiga Workbench 2.0 and MS-DOS, so Windows NT/2000 felt like a good evolution from it's User Interface. Very functional, for sure.

100% agree on Classic MacOS. As outdated as the tech was, it was beautiful because it was elegant without being distracting.

Pretty/ugly and usable are very different things. Sometimes they are in conflict, but mostly they are unrelated.

To the contrary, XP and Vista' soft, round buttons and edges always made me think of a Douglas-Adamsian dystopia. Win2000 was bare bones, square and functional.