The main benefit of an external CSS file is that:
- It can be used on multiple pages; and
- It can be cached so it doesn't need to be loaded on every page.
So, if there is potential for reuse of the dynamically generated CSS between pages or on multiple views of the same page then an external file could add value.
There are several common patterns for dynamically generated CSS.
1. Generating a subset for a page
I've seen this occasionally. A developer decides to limit the amount of CSS per page by only sending what's necessary. I don't imagine this is the case for you but I'm mentioning it for completeness. This is a misguided effort at optimization. It's cheaper to send the whole lot and just cache it effectively.
2. User-selected theme
If the user selects a particular look for your site, that's what I'm talking about. This implies they might select a whole package of CSS and there might be a limited set to choose from. Usually this will be done by having one or more base CSS files and then oen or more theme CSS files. The best solution here is to send the right combination of external CSS files by dynamically generating the page header with the right <link>
elements and then caching those files effectively.
3. User-rolled theme
This goes beyond (2) to where the user can select, say, colours, fonts and sizes to the point where you can't package those choices into a single theme bundle but you have to generate a set of CSS for that user. In this case you will probably still have some common CSS. Send that as an external CSS files (again, caching them effectively).
The dynamic content may be best on the page or you may still be able to make use of external files because there is no reason a <link>
can't point to a script instead of a static file. For example:
<link rel="stylesheet" href="/css/custom.php?user=bob" type="text/css">
where the query string is generated dynamically by your header from who is logged in. That script will look up the user preferences and generate a dynamic CSS file. This can be cached effectively whereas putting it directly in the HTML file can't be (unless the whole HTML file can be cached effectively).
4. Rules-based CSS generation
I've written a reporting system before that took a lot of rules specified by either the user or a report writer and a custom report and generated a complete HTML page (based on the tables and/or charts they requested in the custom report definition) and styled them according to the rules. This truly was dynamic CSS. Thing is, there is potential for caching here too. The HTML page generates a dynamic link like this:
<link rel="stylesheet" href="/css/report.annual-sales.0001.css" type="text/css">
where 'annual-sales' is the report ID and 0001 is like a version. When the rules change you create a new version and each version for each report can be cached effectively.
Conclusion
So I can't say definitively whether external CSS files are appropriate or not to you but having seen and developed for each of the scenarios above I have a hard time believing that you can't get some form of caching out of your CSS at which point it should be external.
I've written about the issue of effective CSS in Supercharging CSS in PHP but the principles and techniques apply in any language, not just PHP.
You may also want to refer to the related question Multiple javascript/css files: best practices?