Opt for a grey puffer jacket and a grey sweatshirt and you'll be the picture of rugged elegance. For times when this outfit is just too much, dress it down by finishing with a pair of white canvas low top sneakers. When temps are getting lower and autumn is in full swing, you'll appreciate how perfect this outfit is for summer-to-fall weather. This ensemble demonstrates how to dress stylishly as you work your way through your teen years.