Mmmm. Your meal sounds amazing, Sarah! Yum!!
Your shoes are yummy, too. I really identify with your problem, because our climates are so similar. I realized recently that I spend most of the winter in boots or in my slippers (which is what I wear at home). On the one hand, this is good news; it justifies the money I want to spend on boots! On the other hand it is bad news, because none of my shoes get worn in that season!
I have similarly been playing around with Mary Janes and socks/tights at home. Mine are not cognac but yellow.
I think for your shoes, the advice to try sheer black is good. And I think a pair of textured hose in a sort of browny-olive (or some variant) might look really good, too. Maybe get out the pants and other skirts/dresses you might want to wear with them and try to figure out what colour combos would be ideal? I think these would look really good with that mulitcoloured patterned (tan/grey/black?) top you sometimes wear with black trousers. They would also look great with other blues in your closet. So maybe sheer navy or patterned navy tights would be another option?