Wear a black and white plaid flannel long sleeve shirt and black ripped jeans to be both off-duty and dapper. Ramp up the formality of this getup a bit by finishing with a pair of tan suede casual boots. A kick-ass outfit that will take you from summer to fall like this one makes it very easy to embrace the new season. If you frequently wonder how to dress appropriately for your age, this ensemble is a good illustration.