A History of Drake’s Merch, ‘Summer Sixteen’ to ‘Certified Lover Boy’

When it comes to style, Drake might not be the first name that comes to mind for some people. But when you’re the biggest rapper on planet Earth, you eventually find your lane. Drake has certainly been able to up his game in recent years, with a love for custom Tom Ford and Stone Island becoming signatures from his wardrobe. 

If Drizzy isn’t sitting courtside flexing Visvim grails or stepping out with $1 million fits in London, he’s got that owl on him. What started out as an imprint early in his career responsible for a handful of merch items has grown into a full-fledged brand on its own. Of course it will always be linked to Drake, but the OVO brand is more than some fan merch now. It boasts flagships in major cities like Toronto, New York, Tokyo, and London. It has collaborated with names like Canada Goose, Clarks, DSquared2, Takashi Murakami, and Jordan Brand. That golden owl can really be a uniform for you, if you want it to be. 

But that hasn’t stopped Drake from producing some great merch along the way as well. Whether it’s a Toronto Raptors giveaway, official collabs with Nike, or a new round of goods on display at the arena stand during his world tours, there have been a vast array of items for his fans to choose from.

With Certified Lover Boy finally here and a new round of Nike T-shirts displaying some signature Drake quotables being used to promote the project getting released at wedding chapels across the country as we speak, we decided to take a look back at some of Drake’s most memorable tour merch. Check out the list below. —Mike DeStefano

In 2013, Drake’s OVO label released an exclusive collaboration with Cash Money Records. The collaboration highlighted the Young Money Cash Money Records label, which gave Drake his start in the rap game. The collaboration with Cash Money consisted of long sleeve shirts, Cash Money logo T-shirts, beanies and more.  All this apparel was sold for just one day at pop-ups in several cities throughout the United States. One of the most memorable items from this drop was a long sleeve T-shirt that featured a reprint of Jonathan Mannion’s iconic photo of the Cash Money crew, which was the cover of XXL in 1999.—Lei Takanashi

One of Drake's biggest merch drops was for his 2013 album Nothing Was The Same. Three pop-ups in Los Angeles, Toronto and New York gave away free merch for just one day. The merch featured the title of the album on the front and the release date on the back. In New York, the pop-up held at Alife got particularly rowdy. The line stretched for three blocks and Drizzy fans reportedly camped out overnight for the merch. However, it was eventually shut down by the New York Police Department after one fan tried to cut the line and was met with a girl holding a box cutter. Days later, Drake performed in Alife’s backyard for one of the streetwear store’s most memorable Alife Session concerts.—Lei Takanashi

By now, everyone knows how big of a Toronto Raptors fan Drake is. From his countless courtside antics to his infamous “We created this” speech outside in the streets of Toronto during the Raptors 2019 NBA championship run, his love for The North’s squad runs deep. The team even has a black and gold OVO-themed alternate jersey. Since 2014, fans have even been treated to Drake Night, which promises everything from Drizzy player introductions to inebriated jubilation when Fred Van Vleet hits a late game three pointer. It also promises some pretty cool merch waiting for fans at their seats. The first offering was some of the best, a black long sleeve T-shirt with a gold Raptors logo on the chest, a Canadian leaf and Toronto area code on the left sleeve, and the signature OVO owl on the back. Plenty of iterations have followed since. The merch giveaway has even evolved into full blown capsule collections between the OVO brand and Mitchell and Ness. There’s also been some more trivial items like an OVO lint roller inspired by Drake’s infamous courtside fit cleanup. But if you want the rarest item, you need to track down that OG long sleeve. —Mike DeStefano

A week before Drake was set to drop his fourth album Views in 2016, he suddenly sent a tweet telling his New York City fans to go out to 135 Bowery Street. What ensued was a pop-up line that stretched around the block. Fans who waited it out were awarded with a Views T-shirt and wristband. The T-shirts featured a Comme des Garçons Play inspired logo and were later sold at various stops on the Summer Sixteen tour a few months later. —Lei Takanashi

OVO Fest is yet another yearly event hosted by Drake. Since 2010, OVO Fest has been Toronto's premier annual music event and has hosted memorable performances from some of rap’s biggest acts including Jay-Z, Snoop Dogg, Kanye West, and more. While the event has provided attendees with the usual merch to mark the occasion over the years, the best example is arguably the items created for OVO Fest 2019. To cater to the throwback theme that featured acts like Ying Yang Twins, B2K, and Chingy, there were T-shirts displaying designs inspired by Pen and Pixel and Now That’s What I Call Music cover art that ruled the ‘90s and early 2000s when copping CDs was still commonplace. —Mike DeStefano

The European leg of Drake’ tour for Scorpion was titled Assassination Vacation. To go along with the name change, there was also plenty of special merch created that was exclusive to each tour stop and the Tour Life web store. Various neon-colored T-shirts and hoodies were available sporting a logo of a Scorpion in crosshairs to play off of the name. The standout pieces gave a nod to cult classic film franchise Austin Powers with official imagery and a psychedelic logo to match. —Mike DeStefano

It’s become a meme of sorts. But one thing we can guarantee whenever new Drake music drops is the plethora of Instagram captions using his lyrics that will follow. It seems that Drake has taken his awareness of this phenomenon to a new level with his most recent batch of Certified Lover Boy merch. The front is simple enough, a small Nike Swoosh intertwined with a pink rose placed at the center of the chest. The back of each black T-shirt is home to various one-liners we can only assume are pulled from tracks on the album. Admittedly, and probably intentionally, they’re pretty corny too. “Should’ve Said You Loved Me Today Because Tomorrow Is A New Day” and “I Don’t Miss…Let Alone Miss You” are some examples of the phrases that are also currently plastered on giant billboards in Toronto. Flexing his official Nike partnership, there is even a design that repurposes the logo of Nike athlete and NBA champion Giannis Antetokounmpo (aka the Greek Freak) to read “I Need a Freak.” 

The pop-ups that have been dishing out the merch lean into the “Lover Boy” demeanor even further by taking place at shoddy wedding chapels across the country. On Wednesday, for example, the T-shirts were available at the Graceland Wedding Chapel in Las Vegas. It’s the type of merch that no normal person can really wear in public without looking silly. But these phrases are peak Drake-isms and definitely set the tone for the type of album we are about to hear. —Mike DeStefano