Here's another styling option for the Factory Skimmer pant in houndstooth. I plan to wear these pants more than once during the holiday season so I switched out yesterday's grey cardigan set with a brightly colored cashmere long-sleeve tee (mine is older from J.Crew), sparkling necklace, and strappy black pumps.
These pants are a cropped length on me. I prefer to wear cropped pants instead of skirts during winter months because the extra length, even cropped, is warmer than a knee length skirt. The dark color of the houndstooth print works well with black or dark grey knee socks to keep my ankles warm.
The Adriana buckle pump from J.Crew is still one of my favorite heels for adding a bit of edge to my outfits. It's hard to find a comparable style that I like as much and without a designer price. The Annalee triple-strap pump by Michael Kors is one that I do like, but sizes are limited by the time it goes on sale at most retailers.