Well, I can say that last fall/winter I lived in two pairs of black ankle boots: one black and one brown. They weren't identicals, but this is what I fell back on repeteadly during the colder months when I needed socks and couldn't wear pumps or ballet flats.
The black pair aren't even real leather - they are pleather - but uber comfy and the pleather is actually a plus in our harsh winters. Doesn't get destroyed by salt crystals. I've had them for a few years.
This season I've upgraded to the stuart weisman oxfords - and they are actually a dark silver, not black.
But I'm sure I'll still get a lot of wear out of the brown ankle booties (they're a dark chocolate brown with suede detailing) because they work better when I'm wearing browns and greens.
