For a more casual look, tuck your favorite pair of pants into the knee-high boots and let the fabric pool around the knees. Next, pair the combo with a cozy knit (a cashmere turtleneck in my case) and a light jacket. While a trench or a pea coat would make this look appear more classic, I love the juxtaposition of a modern, sporty windbreaker (from my new favorite collaboration between Ganni and 66°North!) with tailored, vintage-looking pants.