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Thanks for all the awesome comments!
@Yara – I haven’t used it, but Sloppy looks like it might do the trick.
@Shaun – As others have mentioned, you can’t rely on that. Some networks compress, but others don’t. Those that do, often only do so in certain situations (and some do a horrible job). If you’re interested, I actually wrote a bit about the unpredictability of carrier networks last year’s Performance Calendar.
@Andy – I had the same thought about eCSSential initially, but the initial (though informal) testing I did actually showed pretty good improvements. I know WebKit does handle it rather smartly (at least some versions of it) but I haven’t seen any information yet about how many other browsers do it as well. I’d love to see more formal benchmarking. :)
@Jacques – Unfortunately the media property doesn’t stop all those extra CSS files from downloading. See Scott Jehl’s tests for a bit more on that.