A black windbreaker and a crew-neck sweater are a must-have pairing for many stylish men. If not sure about the footwear, add a pair of dark brown leather desert boots to this ensemble. Keep this outfit in your front hall closet come warmer weather, and rest assured, you'll save a lot of time racking your brain for what to wear on more than one morning. So if you're on a mission for style tips on what to wear as you go through your teens, this pairing is perfect.