This combo of a black shearling jacket and cargo pants is hard proof that a straightforward off-duty ensemble can still be really interesting. Introduce dark brown desert boots to this getup to pull the whole thing together. In the colder months, when functionality is a must, it can be easy to settle for a less-than-stylish outfit in the name of convenience. This outfit, however, is a practical illustration that you totally can stay snug and remain equally stylish during the colder months. Relaxed casual ensembles for gents in their 50s aren't actually that hard, as you can see.