For an ensemble that brings function and dapperness, choose a navy and white plaid long sleeve shirt and a black crew-neck t-shirt. If you want to instantly class up this look with shoes, introduce a pair of white leather chelsea boots to this look. With the departure of snow comes warmer, sunnier weather and the need for a killer getup just like this one. So if you're after style inspo for dressing as a teenager, this outfit is a perfect example.