Recent decades brought about the popularity of the hoodie. However, a hoodie can be considered looking sloppy compared to other casual shirt options. For outerwear, look for modern takes on vintage inspired pieces. The lettermen's jacket has recently made a huge comeback, and looks great layered over a pair of chinos and a fitted crewneck cotton sweater. Retro inspired shoes are a great look, too. Look for fashion sneakers in canvas, such as Frye Men's Greene Lowe Sneakers; or leather, such as Diesel Footwear's Leather and Suede Midday Sneakers.