This smart casual pairing of a dark brown v-neck sweater and a tan check suit is very easy to put together in next to no time, helping you look awesome and prepared for anything without spending a ton of time searching through your wardrobe. Add a pair of chelsea boots to the mix and off you go looking amazing. Seeing as autumn is in full swing, this outfit seems a viable pick for the transitional season. This outfit illustrates that dressing cool as you head into your 50s is totally doable.