Make a navy overcoat and chinos your outfit choice to achieve a dressy, but not too dressy look. Show off your mellow side by rounding off with a pair of white athletic shoes. Keep this outfit in your front hall wardrobe come warmer weather, and rest assured, you'll save a lot of time racking your brain for an ensemble on more than one occasion. Gentlemen wondering how to pull off cool off-duty dressing as you progress through your 20s, you have your answer.