Nail the laid-back and cool look by wearing a gilet and a navy long sleeve shirt. Hesitant about how to round off? Add a pair of blue athletic shoes to the mix to shake things up. So as you can see, this combination is a really savvy pick, especially for transeasonal weather, when the temps are starting to drop. Those wondering how to dress fashionably as you make your way through your teen years, here's your inspiration.