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In July 2011, a few days before the second annual OVO Fest in Toronto, Drake and his camp finally released the OVO gear they had been spotted wearing earlier. The collection, previewed on the OVO blog, included T-shirts and crewnecks with various OVO logos, including their signature owl, and a murdered-out varsity jacket. 

At the time, the October's Very Own site was only a blog, without a webshop yet. At the time, the apparel was the first of any kind of gear or merch they'd ever released. The varsity jacket featured various OVO labels and Drake's albums, Thank Me Later and Take Care​, and the EP So Far Gone. 

Image via October's Very Own

It was available in black, and later red and white, and retailed for $500 at Nomad in Toronto and Nepenthes in New York, where kids lined up to cop, and Drake himself later stopped by.


In the years after, Drake went on to collaborate with Nepenthes, Canada Goose, Jordan Brand, and Parisian retailer Colette before linking up with Roots again. Building off the previous release, Drake and OVO dropped a new varsity jacket, available in two colorways (black/white and green/white). The jacket featured similar OVO insignia and the titles of Drake's albums, including Nothing Was the Samestitched on the chest. 

Roots first began collaborating with Drake at the suggestion of of Matthew Budman, son of Roots co-founder Michael Budman. "Matthew is a friend of Drake's, who's long been a fan of Roots and often wore Roots items on tour and in other public settings," explains Robert Sarner, Roots director of communication and public affairs. The collaboration between the Canadian rapper and the Canadian brand carried on. 

At the end of February 2015, OVO released yet another Roots varsity jacket. The all-black leather letterman featured a patch of the Canadian and American flags on the left arm and an "O" stiched on the front and "OCTOBER" on the back. Only 50 of them were made and were sold at the OVO flagship in Toronto, which opened in December 2014. Drake and Roots sold a similar jacket—in navy blue with brown leather sleeves—seven months later. This past February, they released the pink varsity Drake wore at a Toronto Raptors game. 

Image via October's Very Own

According to Sarner, Drake and his team were always drawn to re-mixing Roots' varsity jacket. When asked what it's meant to work with the hometown hero, Sarner's answer was straight forward: "In a word, amazing. We greatly admire Drake for his music and for how he's such an incredible ambassador for Toronto. His passion for the city has had a hugely positive impact in Canada and internationally."

Drake and camp have been steadily pushing their OVO brand through their own collections and collaborations with the likes of Canada Goose, Jordan, and even the Toronto Raptors. They've certainly come a long way from the July 2011 release—and those that followed—and show no signs of slowing down. 

When asked if we can expect another OVO and Roots collaboration, Sarner was hopeful. "Based on the success of our collaborations with Drake so far, and the excellent relationship that exists between him and Roots, it's safe to say there will be other projects together in the future."

Now, if they'll only release that custom brown varsity Drake rocked to Kanye West's Yeezy Season 2 presentation we'd be good.