October's Very Own (OVO)

Drake's brand, built with Oliver El-Khatib and Noah "40" Shebib, turned an owl logo into one of the most recognizable marks in Canadian streetwear. Its webshop opened on Drake's 26th birthday in 2012, and its first flagship opened in downtown Toronto in December 2014, followed by stores in Los Angeles, New York and London. What makes OVO more than tour merch is restraint: clean basics, outerwear and long-running collaborations, notably with Canada Goose, that sell on quality and the owl rather than the artist's face. It also stays closely tied to Toronto, so buying it feels like buying into a city as much as a rapper.