If the setting allows a laid-back ensemble, you can easily go for a charcoal polo and chinos. Finishing off with black and white athletic shoes is the simplest way to introduce a more laid-back finish to your getup. When it's one of those dull autumn afternoons, what better to spice it up than a seriously stylish outfit like this one? Those who wonder how to sport cool off-duty outfits as a teenage boy, this pairing should answer your question.