If you're searching for a laid-back yet dapper look, pair a tan shearling jacket with chinos. Complement this look with a pair of white and black athletic shoes to give a dash of stylish casualness to this getup. Piecing together a neat outfit can be a bit difficult at times on its own. Enter below-freezing temperatures into the equation, and the whole thing becomes all the more difficult. No worries, this here is your winter outfit inspiration. No doubt, a popular option if we're talking dressing ideas for teenage boys.