This pairing of a black leather biker jacket and black vertical striped chinos delivers comfort and laid-back dapperness. A pair of white canvas low top sneakers looks perfect rounding off your getup. Keep this getup in mind when spring sets it, and rest assured, you'll save a ton of time brainstorming for an ensemble on more than one occasion. Those who are curious how to sport cool off-duty dressing as you get into your 30s, you have your answer.