Era of Prominence: 2009-2011

Early on, Supra was the sneaker of choice for the young singer. It was rare to see him wear anything else, and the kicks became as much a part of his look as were his side-swept hair and purple hoodie. His fans are aware of this—a pair of his Supras were even on display at the Bata Shoe Museum in Toronto. He still wears Supras every now and again, but not as often as he used to. These days, he's taken a liking to Givenchy sneakers.