What I have in mind is a tool that I throw a CSS file and a bunch of static HTML files at, it will try to apply each CSS rule to the HTML like a browser would and remove all the rules that don't apply.
I don't expect it to ascertain if a rule had visible effects. I also don't expect it to consider JavaScript. Just plain CSS and static HTML. It doesn't look to me like CSSnano or LighteningCSS could do that.
Here's a more complete result adding brotli and the aforementioned cpp version:
$ gdu -b *.css *.css.gz *.css.br | awk '{if (NR % 3 == 1) {ref = $1; print} else print $0, "(" $1 - ref ")"}'
623 in.css
197 out.css (-426)
355 out_cpp.css (-268)
345 in.css.gz
185 out.css.gz (-160)
235 out_cpp.css.gz (-110)
284 in.css.br
141 out.css.br (-143)
177 out_cpp.css.br (-107)
I do find that CSSO[1] with structural optimizations can be more effective still, perhaps that will be less true overtime though.
I think once lightning CSS is more stable (in particular, some bugs are addressed around ordering) it will be the clear winner in this space though.