I'm always amazed at how universally terrible graphic design was during the 90s, and I mean at the level of big-name corporations (not GeoCities laypeople). In-house Designers at these businesses (or contractors at the equally big-name firms they hired out to) were presumably well-educated and steeped in the history of the medium, but churned out nearly unintelligible, ugly garbage. Most of the design principles that have given us the mostly tasteful (if bland/inoffensive) modern web were solidified in print by the 1960s. I know the tooling wasn't there yet browser-wise to do anything crazy, but even the image-based graphical elements are just so foreign and weird, like the product of a generation so enamored with the capabilities of Photoshop that they didn't question unnecessary filters, drop shadows, and the placement of text.

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.

New tools. Same as today. Ui designers have been replaced by algos generating nr of clicks, and programmers by JavaScript frameworks and libs.

Remember there was a time, a sweetspot, when browsing was something that would never tax any modern computer?

Nowadays, with my work issued laptop, many web pages (especially apps) load slow or are laggy. They even continue to load stuff while I scroll, which makes everything worse.

And we got used to that, just because each week a new tool, tracker or framework comes out that just needs to be out on the page post haste.

The stuff that web developers get away with through the ages would have gotten other devs fired. Look at how crisp and usable the Win2k UI was, while web pages looked like that.

Web devs today are the same people who put font gifs, colorful backgrounds, flash intros and midi files on websites back then.

There was plenty of good graphical design on the web in the 90s. There was also a lot of bad graphical design which usually gets highlighted today.

There was an underlying issue that web design was difficult before browsers supported CSS 2.1 well. You really couldn't get HTML elements to fit a graphical design reliably. CSS 1 didn't really have the ability and table layouts were pretty coarse. Using raster graphics was pretty much the only way to get fancy designs to look right across browsers.

My issue is mostly with the raster graphics themselves that companies used to try and enhance their sites, rather than the layout or typography of the sites, which is pretty easy to explain away due to the technical limitations of the time. Just lots and lots of head-scratchers from otherwise competent organizations.