This classic and casual pairing of an olive waistcoat and jeans is extremely easy to throw together without a second thought, helping you look sharp and ready for anything without spending too much time combing through your wardrobe. When this getup appears too fancy, dial it down by rounding off with navy and white canvas high top sneakers. Those who wonder how to sport cool casual style as you pass the big 3-0, this getup should answer your question.