A brown shearling jacket and black skinny jeans are a combination that every dapper gentleman should have in his off-duty wardrobe. In the footwear department, go for something on the smarter end of the spectrum and finish off this look with dress boots. In the winter months, when warmth is above all, it can be easy to settle for a less-than-stylish outfit in the name of functionality. However, this outfit is a stark illustration that you can actually stay snug and remain equally stylish in the winter months.