Wiz Khalifa

Image via mistercap on Instagram

Go-to sneakers: Chuck Taylors / Vans

When Wiz Khalifa burst onto the scene in the late ’00s, he became known for his heavy bud-smoking, hit-making ability, and his penchant for wearing Converse All-Stars. Calling his crew the Taylor Gang (both to pay homage to his Pittsburgh-area high school and his love of Chuck Taylors), it was rare to see the rapper in anything but Chucks. As he became a household name off the strength of “Black and Yellow,” Converse took notice and partnered with Wiz in 2013 for the “Wiz Khalifa Collection.” More recently, Wiz has sprinkled in Vans SK8’s (both high and low-cut) into his rotation and the look is catching on as more and more rappers are lacing up the classic skate shoe.