PSA: Very often our clients have a handful of pieces they really like and have never, ever worn because they don't know how. Our advice: try searching the item (ex. a midi skirt-a categorically hard to style piece) on shopbazaar.com, net-a-porter.com or stylebop to see how the experts have styled it.
I had a tiny wool mini skirt that I was afraid I had grown out of...chronologically that is (the saddest way to grow out of something). I searched it on net-a-porter, got some ideas and paired it with a wool Missoni bow blouse I had, black opaque tights and flat boots. And it has, by far, become the winter outfit I am most complimented on!