A few years ago, I built a "front page" for my site, using CSS to implement a flexible column system (instead of fixed width). Works fine under IIS 7, but when I upgraded my web server to 2008 R2, the page content displays but no CSS activity is evident.
I brought in a couple pages from a simpler site that works in a different folder, and that works fine, proving that CSS can behave just fine.
I have compared the two pages, and the only differences are in the accompanying CSS code.
Since css is rendered by the browser my guess is that you have some sort of permissions issue. Are you able to download the css file directly using a link for the source of the page?
So for instance, if in your page you have the following in the html source:
Are you able to go to
http://sstatic.net/sf/all.css
directly from the browser?Use a HTTP debugging tool for your browser to check all the requests and if there is one failing (the one that shout fetch the CSS).
I recommend the free tool "Fiddler."