For comfort without the need to sacrifice on good style, we turn to this combo of a black biker jacket and jeans. If in doubt about what to wear when it comes to footwear, go with a pair of black suede low top sneakers. So so as you can see, it's a sharp, not to mention season-appropriate, ensemble to have in your transitional rotation. Those who are curious how to pull off cool casual style as you progress through your teen years, you have your answer.