As you can see, looking effortlessly smart doesn't take that much time. Team a grey wool blazer with black chinos and you'll look amazing. On the fence about how to complete your ensemble? Round off with brown leather chelsea boots to ramp it up a notch. This look is a really savvy option, especially for fall, when the temps are dipping. So if you're after outfit ideas on what to wear as you go through your teen years, this outfit is an amazing example.