This combo of a white and black horizontal striped long sleeve t-shirt and charcoal jeans is hard proof that a pared down off-duty look doesn't have to be boring. With shoes, you can take a classier route with a pair of black leather derby shoes. This one is a viable pick when it comes to putting together a standout ensemble for unpredictable fall weather. Well into your 30s, you probably want to start dressing like a grown-up. In this case, getups like this prove useful as a source of inspiration.