A navy blazer and charcoal dress pants are absolute staples if you're planning a sharp closet that holds to the highest menswear standards. A nice pair of dark brown suede desert boots is an effortless way to power up this look. In winter, when practicality is critical, it can be easy to settle for a less-than-stylish outfit. However, this outfit is a practical illustration that you can actually stay cozy and remain stylish at the same time in winter. A great combo as you transition into your fifties.