For an outfit that's effortlessly sophisticated and GQ-worthy, wear a brown blazer and brown chinos. For something more on the classy side to round off your outfit, introduce dark brown leather chelsea boots to your outfit. While it can be a bit nerve-racking and time consuming to stay fashionable on extra cold days, it's ensembles like this that prove it's actually possible. As you can see here this getup is something you can totally wear as a 50-year-old man.