What kind of shoes (not athletic shoes - think more of a clog, mary jane, or sandal) do you recommend for someone who overpronates badly, and also needs some firm cushioning?

Talking to any Dr. they will tell you there is no kind of sandal that will be good for the type of feet problem that you have.  I also suffer with this and have had trouble for many  years with shoes.  In saying those facts there are times when you just have no desire to stick another tie up shoe on your feet especially in this hot weather.  I normally try to pick my days to wear my sandals to save my feet as much as I can.

One type of sandal that I have found comfortable is the Dansko Clog.  You can find these at Cabelo's.  They are made well and have anatomical contours and cushioned floorbed.  I have included a brown pair of the Sienna clogs. 

Another pair of  shoes you might like is Nike Flip Flops.  I wear these alot out and about and they truly are the most comfortable pair I have ever owned.  Now for long walking trips I would not recommend them but to run up town or outside for awhile they are great.  My favorite are the Nike Comfort Thong as these seems to keep my feet in great shape. 

Hope some of this helps and I sympathize with you on what you are going through.

Thank you from your IMshopping Guide