For an outfit that's pared-down but can be flaunted in many different ways, go for a charcoal shearling coat and chinos. Let your outfit coordination savvy really shine by finishing this getup with charcoal casual boots. While it can be a bit nerve-racking and time consuming to stay on-trend in uncomfortably cold temps, it's ensembles like this that prove it's quite doable. And if we're talking dressing ideas for guys over 50, this outfit looks great on most gentlemen.