This casual combo of a red and black plaid long sleeve shirt and black jeans is a winning option when you need to look dapper but have zero time to spare. Switch up your outfit by finishing off with chelsea boots. This getup is an obvious choice if you're looking for a kick-ass look that will take you from summer to fall. Guys who wonder how to sport modern off-duty style as you work your way through your teen years, this pairing should answer your question.