This pairing of an olive long sleeve shirt and navy chinos combines comfort and functionality and helps keep it low-key yet current. If you need to immediately lift up this outfit with footwear, add a pair of dark brown leather casual boots to the mix. This outfit is a viable option if you're looking for a cool summer-to-fall look. Gentlemen who wonder how to rock cool off-duty outfits as you step into your 30s, this combo should answer your question.