Hi Katie - Like a whole lot of other women in the forum, I have some pretty nasty foot issues, and, on top of that, a problem with my knee, which made the foot issues worse. I totally sympathize with you, and I'm sorry you're having to deal with foot problems, too. I have had to change my style a bit because my foot is most comfortable in regular walking sneakers with custom orthotics. BUT my style is fairly casual with elements of RATE, so I've also decided to embrace sneaker chic, which works for me, especially in the summer.
Some of my "sneaker chic" choices: Reeboks Classics, Cons-look alikes made by Simple (no longer available), but there are other choices like Josef Seibel, etc. Other brands I've been finding comfortable are some Clarks (like Shannon noted, I get them in wide, which means sometimes I have to add pads in the other foot to stop them from slipping). Also, Alegria, Cobb Hill (made by Reebok), Munro (there actually some cute ones), Sofft, and Softwalk. Zappos is my friend. I've ordered countless pairs of shoes to try on and wear at home, and I've sent countless pairs back. Nordstrom, also, but they tend not to have anything but standard widths in their stores.
Here a few specific choices that are working for me, but I don't do heavy duty walking in them.
Oxfords - these are actually really comfortable, and I can walk for longer in these than any of the others.
http://vip.zappos.com/cobb-hill-ivanka-mist
Sandals
http://vip.zappos.com/sofft-be.....-foil-goat
http://vip.zappos.com/softwalk.....ed-leather
http://vip.zappos.com/munro-am.....ack-nubuck
Good luck, and I hope you'll start to find some shoes that will be comfortable, and that you won't have to change your style or your style descriptors.