For casual sophistication with a masculine twist, you can go for a navy blazer and a white and brown vertical striped dress shirt. Introduce tan suede desert boots to the equation to effortlessly up the cool of this look. During the winter season, when warmth is everything, it can be easy to settle for a less-than-stylish look in the name of practicality. This look, however, proves that you can actually stay comfy and remain equally stylish during the winter season. This ensemble illustrates how 20-year-old gentlemen score in the fashion department.