This combination of a blue denim shirt and navy chinos is very easy to do and so comfortable to wear as well! If in doubt about what to wear when it comes to footwear, complement your ensemble with black and white leather low top sneakers. During the winter months, when functionality is paramount, it can be easy to surrender to a less-than-stylish outfit in the name of convenience. This outfit, however, is a bright example that you can actually stay warm and remain stylish during the winter months.