is the grey dark or pale pale grey imo wont work over black, something stronger like purple or magenta or vibrant like pink or red. match tights to your shoes however if you wear black shoes you could wear a really fun coloured pair of tights and wear a black bolero jacket. match nail varnish to your tights then!
That's a lovely bolero, it will look nice over a black dress. As its evening I think sheer tights will look best with black heels. As it's a classic safe look. If you go for grey shoes, then I think keep the tights nude as the shoe colour matching the bolero will pull the outfit together. I would avoid the coloured tights as it can be hard to pull off as the tone and denier is important too.
You could be right it might be fabulous combination. I think it depends on the dress really and probably how legs are as the colour emphasises calf size, ankle with etc, whereas, nude just makes legs look natural with a shimmer maybe amd sheer black is great as the edges outline legs and make them look longer and thinner esp if wearing heels.