A brown overcoat and a turtleneck are among those wear-anywhere-anytime pieces that have become the absolute mainstays in any modern man's arsenal. Hesitant about how to finish? Introduce a pair of dark brown leather desert boots to the mix for a more casual twist. This combo is basically a must-have if you're looking to stay snug this winter season and look equally stylish. Rest assured this look is something you can totally wear as a 50-year-old man.