What colour shoes/boots to wear.

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.

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

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?

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.

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.