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Windows 98 perhaps. 2000 if generous.

Yes, they have the “Windows Classic” look and feel.

I find it a bit amusing that were they to "update" their look to that of the flat Windows 8+ UI, it would probably entail the removal of a lot of code.

...and yet even on a 25MHz 386, no one complained about the slow drawing speed of the "fancy" 3D buttons in Win3.x.

Well, modern flat design generally also includes a much more animated interface, which would probably entail the addition of much more code. And I don't think the drawing speed of buttons was ever a very strong reason for the rise of flat design - though I completely understand your distaste for it.

Wine actually has (mostly) functional theming support-- point Wine to a .msstyles theme DLL and it'll draw themed controls (rather than the Windows Classic style default).

They just don't ship a theme with Wine; understandable for licensing reasons (they can't distribute Microsoft's designs), but it means that Wine looks like Windows 2000 out of the box.

The .msstyles support in Wine was terribly slow last time I tried it. Has it improved?

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