Here's an outfit that I put together specifically for comfort while walking to work. For the walk I wore my Bastien short boots, and packed the ones you see here (which are comfortable, but not 3 miles' worth of comfortable) in my backpack for swapping once I got to work.
I ended up with a pair of Ecco boots, which have the bonus of being waterproof, and a pair of Romika short boots, which pretty much feel like slippers, only with really good arch support. Both meet my criteria of being cute enough to wear with most outfits during the walk, or even for the whole day if I don't feel like carrying extra shoes. My feet are happy.
Dress: Red Dress Shoppe
Cardigan: H&M
Tights: Sock Dreams
Boots: All Black