A black crew-neck sweater and boyfriend jeans paired together are a covetable combo for those who prefer casual outfits. If you want to effortlessly bump up this look with shoes, complete your ensemble with black leather ankle boots. During the winter season, when practicality is prized, it can be easy to surrender to a less-than-stylish outfit in the name of functionality. However, this outfit is a clear example that you can actually stay toasty and remain equally chic in the winter season.