Okay,
So I have seen lots of posts that mention CSS files aren't rendering/working in the IIS 7 environment, with the solution being to add the static content component.
I am having the same issue, but on a different platform. I'm attempting to configure a new windows server 2012 with IIS 8. The application I am running is a 3.5 app, and I have the necessary components to have the app working, but the CSS from the theme file and the web sites CSS aren't rendering/working.
I have attempted the static content component fix from the IIS 7 posts I have seen, but that did nothing.
What did work was running the command to get the classic asp up and running.
%SystemRoot%\system32\inetsrv\appcmd migrate config "Default Web Site/"
Not sure why this worked, but hopefully this will help others with a similar issue. Perhaps someone with more knowledge than me can help me understand why this worked.
Thank you!