H.E. by Mango Patchwork Sweater, $70
Step up your casual game with this deceptively simple crewneck sweatshirt. The black contrast piping tones things down a little, while the elbow patches make it really dope. On mild days, this thing can be worn by itself over black jeans and sneakers like Chuck Taylors (beat up, of course). When the weather gets really bad, throwing a black leather jacket over it will make you look like a badass without looking boring.