If the situation permits a casual menswear style, make a black bomber jacket and a white crew-neck t-shirt your outfit choice. Finishing with charcoal athletic shoes is a simple way to infuse a laid-back vibe into this outfit. So as you can see, it's very easy to look amazing and stay toasty when cooler days are here, all thanks to getups like this one. Those wondering how to wear cool off-duty looks as you work your way through your adolescence, this pairing should answer your question.