I'm with dickiedavismincepies, the high street is hardly an indicator of high fashion. And fashion is what goes out of fashion, anyway.
If the colour and shape suit you, wear it. I think opaque tights and nice pair of possibly black swede hills would work. I would not go for stilettos, as they may be a bit too flimsy with a tight dress. Also, I would probably have some sort of elegant cardie on top to make it more casual.
Can you not post a pic so that we can be nosey give you more accurate advice?