If you love relaxed dressing, why not test drive this combo of a grey long sleeve t-shirt and white ripped jeans? To add some extra flair to this outfit, add a pair of low top sneakers to your getup. Keep this combination in your head when spring arrives, and we guarantee you'll save a ton of time brainstorming for what to wear on more than one occasion. Gentlemen wondering how to wear cool casual looks after 30, you have your answer.