I get asked all the time which shoes are best for Eli's SMO (supra malleolar orthotic) braces. We have found Van's SK8-HI tops with a zipper in the back to be our favorite - they fit over his SMO's perfectly and are easy to get on. The trick is to size up a little. Eli is currently a size 5.5 so we bought size 6.
I think Eli approves :)