Nail the casually sleek ensemble in a tan shearling jacket and a navy wool turtleneck. Tan suede work boots offer function, but with a fashion-forward effect. During the winter months, when practicality is critical, it can be easy to surrender to a less-than-stylish getup. But this getup is a bright example that you can actually stay cozy and remain stylish in the winter months. This ensemble demonstrates that as a middle-aged guy, you have a wide range of sartorial options.