This pairing of a tobacco crew-neck sweater and black chinos is on the off-duty side but guarantees that you look sharp and truly dapper. Why not take a classier approach with shoes and introduce a pair of burgundy leather chelsea boots to the mix? This one is a viable pick when it comes to a cool ensemble that will take you from summer to fall. As you pass the big three-oh, you probably want to start dressing more maturely. In this case, looks like this are perfect as inspiration.