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Many elements were owed to CRT displays and larger pixel sizes, so rather domain specific. E.g., the mandatory drop shadow typography wasn't to be seen in print. On the other hand, I wouldn't like to witness modern screen design on a CRT. Moreover, the 1990s came just after a massive retro design trend in the 1980s and there were still some informal reference to 1950s design around, countered by a rather blocky "who cares" trend (probably rooting in free-style/low-end design as featured by April Greiman in screen design and new electronic trends in print as by Emigre Graphics), even featuring illegibility. At the same time any custom elements had to match the few "probably installed" type faces (Times/Times New Roman, Helvetica/Arial, Verdana, Courier/Courier New, maybe Symbol). Moreover, fonts rendered in sizes relative to OS presets, most probably what was 12px on a Mac rendered like 14px on Windows (which is huge on a CRT in 72dpi standard resolution), and custom elements had to provide visual stabilization to accommodate the design to the various forms of rendering. Last, but not least, the entire environment of the presentation was rather blocky, from OS elements to the housing of the CRT, and you had to accommodate to this, as well.

Yes, the drop shadows introduced in Win98 (IIRC) really helped readability of filenames on top of desktop wallpapers. It was a much nicer method than just backgrounding the text with a fixed colour like Win95 did.

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