Why not pair an olive military jacket with navy jeans? These pieces are very practical and will look amazing when teamed together. For a more laid-back feel, introduce a pair of high top sneakers to your outfit. So if you're on the lookout for a knockout getup that will take you from winter to spring, you found it. Those who are curious how to pull off cool off-duty dressing as you make it through your 20s, you have your answer.