If pragmatic Paige (see: key characters in the Mata Morrow mystery series) were offering packing advice, it would undoubtedly be that you have to pack around your shoes. They are the foundational aspect of preparation for any travel endeavor. So - go ahead and think about packing your ruby slippers, then consider the possibility that they are one of the very good reasons to leave home.
Check out Fashion Girl's excellent post (with a wealth of links!) about shoe selection, domestic or international, logging miles urban or outdoors. IGNORE the image with those ruby-red stilettos, bringing to mind the folly of showy shoes when on the road.
As always, comfort and versatility are key. You'll thank yourself for stowing those shoes in a separate waterproof bag. My dream travel footwear includes Naot boots for winter, Bjorn loafers for spring, Ecco sandals for summer, Dansko ankle boots for fall and Crocs (really - they come in so many different styles and colors now) for every trip and season.
What's your go-to footgear for the season ahead?