I guess I was picturing more of a knee length walking short.
My thought is (a spin of Angie's theory) that when you are walking miles and miles (which you will) on a very very hot day in DC you must be comfortable.
If a slip on cute sneak won't fit the orthotic, you are going to have to be creative and make a few allowances.
Look for the cutest sneaks that will fit your orthotics
Here's a cute skimmer version from Converse website:
http://www.converse.com/?CSID=.....es/505629F