Ovo Varsity Jacket

While it's far from unique for modern artists to have a clothing brand, Drake's October's Very Own has proven itself to be one of the longstanding success stories. With stores in Canada, the US, and the UK, collaborations with Jordan, BAPE and Takashi Murakami, and special Toronto Raptors OVO edition NBA jerseys, the owl is as much part of the fabric of Toronto street culture as Drake himself. Drake originally started OVO in 2008 as a blog with long-time friends Oliver El-Khatib and Noah "40" Shebib. In recent years, they have branched out to partnership deals with American sports leagues, resulting in wildly popular OVO Varsity Letterman jackets, representing several teams from the NBA, NHL and NCAA college sports. Next to the team editions, OVO has also made varsity jackets with fellow Canadian lifestyle brand Roots.