You can automate it by writing a linker that concatenates the CSS files into 
a single one (same for JS ?) and emit a new artifact for the all-in-one 
file.
There's no built-in solution for that, because the <script> and <stylesheet> 
elements in gwt.xml files take URLs, not file paths; the URL can then just 
happen to match a file that's in a "public" path, but there's no relation 
between those apart from "naming convention".

...but you could also use ClientBundle to have the CSS inlined in the 
compiled output (and make your widget take an instance of the bundle as 
constructor argument so you can easily override the default style; which in 
ClientBundle's world means the old, default CSS can be completely left out 
of the compiled output).

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