At one of my previous jobs we had a massive amount of CSS to handle; we had the global styles, then section/page specific styles and on top of both of those we had different styles for various versions of the application (as the same application and content ran many sites).
The solution we came up with was not too dissimilar to the one discussed in this months A List Apart article Progressive Enhancement with CSS and that article is well worth a read. But I also thought I’d write a little about the setup that we came up with and how it worked out for us.
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