Lace up doc marten type boots, loafers, heeled ankle boots. In my opinion it needs to be either something that is form fitted around the ankle (like doc martens), bare around the top of the foot/ankle (like loafers) or has a heel for height or some other type of structure/shape (like heeled ankle boots). Something with a heel or a platform looks better than a completely flat shoe IMO. This is because you have a pant that is unstructured/loose at the bottom and you need something with some shape and structure as a shoe to keep it from looking sort of sloppy or shapeless, for lack of a better word. Answer from redalmondnails on reddit.com