I notice not many people have downloaded the plugin Combine CSS. Without it, I don’t know of a better way to automatically combine CSS files. I was wondering, are 99% of the developers using WordPress just working in a single stylesheet? Is there some other way to combine CSS without the Combine CSS plugin?
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If you have shell access to an Apache server, Google’s Mod Pagespeed is a great way to do so automatically at the server level. It has really powerful options for doing much more than just combining CSS and speeding up your sites.
mod_pagespeed
mod_pagespeed speeds up your site and reduces page load time. This open-source Apache HTTP server module automatically applies web performance best practices to pages, and associated assets (CSS, JavaScript, images) without requiring that you modify your existing content or workflow.