A shearling jacket and charcoal chinos? It's an easy-to-create ensemble that any gentleman can sport on a day-to-day basis. Send an otherwise all-too-safe outfit in a sportier direction with a pair of grey athletic shoes. This ensemble is a viable option if you're picking out a knockout look that will take you from summer to fall. This getup should encourage anyone who had doubts about wearing casual outfits as a guy in his fifties.