No matter where you find yourself over the course of the day, you can rely on this relaxed combo of a grey plaid short sleeve shirt and navy jeans. You can get a little creative when it comes to footwear and complement your look with a pair of black leather chelsea boots. In the winter months, when comfort is a must, it can be easy to settle for a less-than-stylish outfit in the name of convenience. However, this outfit is a striking example that you totally can stay warm and remain stylish at the same time during the winter months.