For comfort dressing with a modern twist, opt for a black and white vertical striped silk long sleeve shirt and navy chinos. Add white and navy athletic shoes to your ensemble to make a dressy outfit feel suddenly fun and fresh. This look is also great if you're in search of hot weather wear to get through a boring day. Those who wonder how to pull off cool off-duty outfits as you progress through your adolescence, this getup should answer your question.