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.
The Bastiens have been getting a lot of wear lately, so much so that I recently went scouring both the internets and the stores in search of some additional walking shoes, because even the best pair can't be worn every day for 3 (or more likely 6, because I often walk home too) miles of walking.
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
Tights: Sock Dreams
Boots: All Black