This summer I started wearing skirts to work and like it so much, I want to continue into the fall. We have cool weather so above 45 most of the time with very little snow or slush, so I think it should be doable with some tights.

The only (and big) challenge is shoes. I am a committed comfortable, wide, flat shoe wearer - think Birkenstocks, sandals etc. I am ok with stumpy. What sort of shoes should I look for? Links to specific brands/shoes that have worked for you would be great.