For a look that's casually neat and gasp-worthy, choose an olive overcoat and navy jeans. To introduce a little fanciness to this look, introduce black suede chelsea boots to the equation. During the winter months, when functionality is above all, it can be easy to settle for a less-than-stylish getup in the name of functionality. This getup, however, is a striking illustration that you totally can stay comfy and remain stylish at the same time during the winter months. This combination demonstrates that as a middle-aged man, you have a vast array of sartorial options.