Pair a black leather harrington jacket with skinny jeans for both on-trend and easy-to-create getup. Our favorite of an infinite number of ways to complete this ensemble is with black and white athletic shoes. As you can see, this look is a really savvy pick, especially for in-between weather, when the temperature is falling. Think it's hard for guys in their forties to master edgy off-duty dressing? This pairing will prove you wrong.