Linux kernel code runs on a 4K stack on x86. Hence they care. What they use to check that, is a perl script they wrote, which you may find as scripts/checkstack.pl in a recent kernel tarball (2.6.25 has got it). It runs on the output of objdump, usage documentation is in the initial comment.
I think I already used it for user-space binaries ages ago, and if you know a bit of perl programming, it’s easy to fix that if it is broken.
Anyway, what it basically does is to look automatically at GCC’s output. And the fact that kernel hackers wrote such a tool means that there is no static way to do it with GCC (or maybe that it was added very recently, but I doubt so).
Btw, with objdump from the mingw project and ActivePerl, or with Cygwin, you should be able to do that also on Windows and also on binaries obtained with other compilers.