For a look that delivers practicality and fashion, consider pairing a grey wool blazer with grey sweatpants. Our favorite of an infinite number of ways to finish off this look is a pair of charcoal athletic shoes. Keep this combination ready to go when spring comes, and we promise you'll save a lot of time getting dressed on more than one occasion. Those wondering how to sport modern casual dressing as you progress through your teen years, this combination should answer your question.