Could someone describe a no-brainer outfit that would look good in Wash DC where I have to wear sneakers with support for walking 8 hour days?

This is my ultimate fashion challenge. I seem to have a mental block about it or am making it harder than it is.

Challenges:
orthotic must fit in shoe with insole covering it (usually this means some type of fashion sneaker or running sneaker)
must be able to wear no-show socks

(PS I will take my brulee gladiators for times when I am not walking a lot. They are very comfy for me, but not for walking long distances when I need the support)

(PSS I own gray Converse and my orthotics fit in them with a pad over them but what to wear with them in summer?)
Thank you for de-mystifying this for me!