What colour shoes/boots to wear.

I too am old school and wouldn't mix brown and black like I wouldn't mix navy and black. Sadly beyond that I am no help.

Too much brown in my opinion. Black footwear sounds safer but why not try different colours, if you have some already, or even try different colours in a shoe shop.

Black boots would be fine, but if you don’t like that idea, and worry that a similar shade of brown as the skirt and top would be too much, then have you considered a contrast, such as tan, cream or red?

I think leopard print boots are a thing this year, too,

I wouldn’t wear black boots with a dark brown skirt, I’d go for a lighter shade of brown, tan or mocha - suede would look nice for a contrasting texture.