How to make a theme with more than one CSS file?

This article should answer your question:

Add a style switcher to your wordpress theme

The article that I have linked above explains and walks you through on how to add a stylesheet switcher to your admin panel for your theme.

It walks you through on how to use and add options to your theme. This is particularly intuitive if your developing a theme for a client who once in a while may want to change their colors / imagery or something on a whim.

I have used this numerous times when theme developing. Also in using this method you can add as many stylesheets as your heart desires.

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