Six Items That Define the Rapper’s Style

Honorable Mentions: Gruppo Vava V Jacket, Iceman Hooded Work Jacket, Bullethole Jacket from It’s All a Blur Tour

At its height, October’s Very Own was in a class of its own. Beginning as a blog in 2009 before becoming a record label in 2012, the brand grew so quickly that a clothing line and flagship stores soon followed. By the mid-2010s, the all-seeing OVO owl sat firmly atop the Air Jordan collab hierarchy aesthetically, while being among the first to publicly platform future superstars like The Weeknd sonically.

Being down with The North was not historically cool stateside, but that changed in the mid 2010s when October’s Very Own became an apparel player with a flagship on La Brea Ave in Los Angeles and a satellite shop on Bond St. in New York City. The pinnacle piece was the varsity jacket created in collaboration with fellow Canadian brand Roots, infinitely rebranded through licensing partnerships, but worn most boldly when he attended Yeezy Season 1 in New York. Drake has rocked plenty of more vibrant, viral jackets since, but nothing defines his career quite like the signature piece from his own brand.