I am infatuated with these Docs. They may not be comfortable due to the heel, but I simply must try them. In the winter, I primarily wear black - almost always either black pants or a black top - with white or grey or red... sometimes cobalt, and I just bought a natural coloured sweater (oatmeal?). But more often, it is black again with one of those colours as an accent. I have black/grey and red/black plaid pants. And I recently bought a blush leather jacket (I must post pics - it is DIVINE).
When I wear dresses, I like to wear boots, and I almost invariably wear black tights.
These boots come in both black (which I know would coordinate with everything without question) and oxblood/burgundy. The red shows off the boots much better, but I wonder if they would be as versatile, or if that really matters (I have lots of shoes and boots). The heels would be flattering with dresses, but would the red make them costumey or silly looking with a dress (generally a black or black and white dress)?