Here's the thing.
I absolutely love pencil skirts.
There's just something about them.
They're classy. Business appropriate. But sexy at the same time.
If I could wear one of these every day, I would.
Or not. Because I mostly wear jeans because of all the running around that I do.
My advice? Don't over-think it. Just go with it. Your shoes may get a little dirty, but you can easily clean them with warm water and soap. Mary Janes are actually really sexy on adult women. You're crazy if you think you look like someone's grandma, even if you are someone's grandma.
The point is, get outside of your comfort zone. Use the white shoe! Now, do I have to sell you on mixing patterns as well?