The issue with doing it this way is that you're making the CSS processor doing unnecessary work. If you are writing:
div#sidebar > form#login-form input
then you are actually searching for input, then #login-form, then form, then #sidebar, then div. It adds up on a really big site. If you had just written
#login-form input
you get the same selection without the additional processing. Even if you want to track the full "stack", don't use those extra tag qualifiers.
Why the hell doesn't the lookup code work left-to-right, like you write CSS? Is there a good reason, or is it just there to make you eschew best practices after you learn them?
Good source: http://code.google.com/speed/page-speed/docs/rendering.html