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Just like javascript compressor, i use the same technique for css. First, i merge all the file into a single file and then compressor. But, the behaviour of HTML is not same as earlier with multiple css file. What is the best way to minimize the the no of CSS File?
Check the order of loading you files into the merge script, like others have mentioned.
I found Sprockets to be good tool for dependency management. It keeps track of changes in your files and outputs a single file, ready for compression. It will also work with your CSS files.