This off-duty pairing of an olive sweatshirt and olive sports shorts is super easy to throw together without a second thought, helping you look amazing and ready for anything without spending a ton of time digging through your wardrobe. To give this look a classier touch, complete your look with a pair of yellow suede desert boots. Gents who are curious how to wear cool casual dressing as you are making it through your teen years, you have your answer.