Chitown asks: "What do you like for a warm winter coat these days? I'm not a big fan of big and puffy coats, and generally anything I see that's remotely stylish for a casual setting wouldn't allow you to spend more than 5 minutes in a good Chicago winter. Bonus points if it could also go with a pair of wool pants for work, but that's probably asking too much." Answer: Chicago winters are nothing to fool with, and the warmest option is always going to be down-filled. Most of us probably think of big puffy coats when we think of down, but it's not necessarily the case—there are relatively trim options that will look great with your wool trousers, and some of them are rated to -20 degrees F or lower. The key is to stick with clean lines and as little quilting as possible. The crème de la crème, if you have $1,400 burning a hole in your pocket, is something like Moncler's Ottoman coat, which basically reads like a menswear topcoat adapted for climbing Mount Everest. Cheaper options: Ralph Lauren RLX Parka ($600) with faux fur trim for rolling like a boss. Clean and simple commuter coat ($270) from Lands' End.