Thanks, ladies. Yesterday ended up getting quite busy so I haven't had time to sit down and look at your suggestions until now.
Gretchen, I've never tried M Gemi or even seen them IRL! They have some cute kitten heels on the site! I wonder if there's anywhere I can try them on IRL...
Alice, those gentle souls look really promising! They even look like they might have some arch support. Will def have to give them a try.
Alexandra, those look really comfy! I'm not sure Aravon works for me - they tend to be a little too high volume - but if I can find these in a store I'll try them on.
Angie, I do love red shoes! I am not sure how many different shades of red I can get away with in one outfit though, lol. The hat is tomato, my clutch is cherry patent (although I could use a black or gold one instead, or even turquoise...). It's quite hard to match red shades exactly in my experience.
I'll definitely go downtown and try on a bunch of naturalizers. I didn't know that about clarks - I haven't tried any of their shoes for years actually. Good to know. Sometimes I can get away with wider shoes if the ankle strap isn't too loose.
Robin, unfortunately I've not had good experiences with faux patent. My feet are somehow really sensitive to getting cut up and blistered by stiff shoes.
AT, thanks for the reminder about DSW. If I'm downtown I really need to remember to stop in and see what options they have.
Fashintern, those look comfy but a little too casual for what I'm looking for.