A black and white gingham overcoat and chinos are the kind of casually classic pieces that you can wear for years to come. Feeling adventerous today? Switch up this look with a pair of burgundy double monks. During the winter months, when functionality is crucial, it can be easy to surrender to a less-than-stylish outfit. This outfit, however, is hard proof that you totally can stay comfy and remain equally stylish in the winter months. Outfits like this help welcome this next milestone that is your 50s with class and confidence.