An olive overcoat and chinos are among the basic elements of a smart menswear collection. To add a more casual spin to your look, complete this getup with a pair of tan desert boots. In the winter season, when practicality is the priority, it can be easy to surrender to a less-than-stylish outfit. This outfit, however, is a striking illustration that you can actually stay snug and remain stylish at the same time during the winter season. Wondering how to dress as you work your way through your 20s? This pairing is a great illustration.