Although I agree that 27 CSS files are completely nuts, and that ideally this should be combined and minimized, there are some use cases in which splitting style sheets makes sense.
Consider this: You are working on a sub site that requires a large number of CSS rules that are not otherwise used on the site. If there is no guarantee that the user will visit both the sub-site and the main site (and, therefore, will use caching), it makes sense to store two stylesheets, so the browser does not need to read a huge stylesheet to see if something matches the HTML document.
Now this is not an ordinary case, but it is happening. An example is a large corporation with a large number of divisions with their own sites. They can include one style sheet for all their common styles (corporate specific interface, etc.) and separate style sheets for layouts and overrides.
However, I highly doubt that 27 styles have always made sense. The original author probably didn't have a clue, and he thought he was more structured that way. Modulated CSS is actually pretty neat, but it should always be combined and minimized before it reaches the client. This is a general method of working in SASS . You will have many partial style sheets for specific parts or functions of the site, but as soon as you press Ctrl + S , it will automatically be combined into one neat little package.
Now you could figure out in what order the CSS files are loaded on your site by simply visiting each page and noting the order. It will be a tedious job, and there is no guarantee that it will ever really pay off, but it can be done.
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