This skirt is probably intended to be a spring or summer skirt. But with boots and a wool turtleneck, I think it works for winter.
The skirt is Ann Taylor via Goodwill. The sweater is Banana Republic (100% merino wool) via Goodwill. The pink t-shirt underneath is from Target clearance and the boots are also from Target. This whole outfit was under $50, and considering the boots were $35, I think that is a pretty good deal.