Rumours began that he was dating Rihanna-a now on-again/off-again relationship central to Drake lore. While his outfits looked hastily put together and the proportions were far from perfect, this period showed that Drake was beginning to understand that how he looked and what he wore was a direct reflection of his persona and standing as an artist.Ģ011 was a big year for Drake. His 2010 wardrobe still consisted of a steady diet of PLAY Comme des Garçons, ill-fitting leather jackets, baggy denim and plenty of Redwings. The album was relatively devoid of fashion references, with the exception of Rolex on “Light Up” and a nod to the crew’s love for Redwing boots, when he proclaimed “OVO clique, Redwing Boot gang.” Although OVO caught on-Redwing Boot gang did not. He harbored an affinity for PLAY Comme des Garçons, Comme’s entry-level mass market label readily available at your local mall, even rapping about the Filip Pagowski-designed heart logo on “Congratulations.”Įven in 2010, when Drake’s debut album Thank Me Later dropped and he embarked on a North American tour, his style still was very much the same. Still, the fashion foible was emblematic of the emcee’s style at the time: the shoes were Jordans, just not the Jordans.ĭuring the mixtape years, Drake often stepped out wearing Jordans or, oddly enough, Redwing boots (more on that shortly). Though eventually it was revealed the shoes were “customs,” wearing altered Jordans was still a serious misstep nonetheless. In 2009, Drake famously wore a pair of Jordans that were almost immediately panned as “fakes” by the online sneaker community. It wasn’t just fake Chanel wallets, however. In “From Time, he calls buying a Michael Kors bag “a weak attempt at flexing” in retrospect and on “Do Not Disturb” he talks about when he bought a then-girlfriend “a fake Chanel wallet.” While these early bars indicated a certain level of fashion-proficiency, Drake eventually acknowledged that in the mid-‘00s he didn’t know much about the labels apart from the name-hence the excessive name-dropping-and was simply trying to fit in. He rapped that there wasn’t “a pair of Louis shoes ain’t purchased” and about “denim that’s too expensive” on “Where To Now,” while showing he was tuned in to current trends on “Must Hate Money” when he said “fresh Jordans, new pants my true religion is money, check out the pant’s seam.” On “Man of the Year,” it became clear that he was trying to emulate other successful rappers, boasting “I be wearing the same Gucci that Jeezy got and I be buying the Louis that Kanyeezy copped.” More conspicuously, Drake showed up to the 2009 Much Music Video Awards-the Canadian equivalent of the VMAs-wearing plaid and Louis Vuitton, the exact same combination he rallied against in his records a year prior.Īs he released his second and third mixtapes, Comeback Season and the critically-acclaimed So Far Gone, Drizzy graduated to a slightly more braggadocious tone in regards to his fashion choices. On his debut mixtape, Room For Improvement, Drake raps about “Timbs” on a pair of tracks, while also adding he’s “sick of seeing chicks in that Louis V and that plaid shit cause it’s a bad fit.” While the part-time MC may very well have been wearing Timbs, name-checking Louis Vuitton stands in stark contrast to the white T-shirts he was wearing in ‘07/08.
Like many mixtape manglers, there was a particularly strong disconnect between the clothes Drake was rapping about and the clothes he actually wore. When Graham took up the mantle of Drake-his middle name-he became an entirely different person. For all intents and purposes, this is where the then aspiring rapper’s style journey truly begins.
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