Before he was Drake, the Canadian superstar was Aubrey Graham, a teen who found mild success on beloved teen drama Degrassi: The Next Generation. His character, Jimmy Brooks, skewed towards what was popular at the time: baggy hoodies, polos over T-shirts, jeans.

While unfair to judge a person based off his tv persona, Graham’s real-life sartorial choices were equally lacklustre—made evident by his outfit choice for the 2005 Teen Choice Awards. Clearly Graham did not possess an innate sense of style.

For all intents and purposes, this is where the then aspiring rapper’s style journey truly begins. When Graham took up the mantle of Drake—his middle name—he became an entirely different person. Like many mixtape manglers, there was a particularly strong disconnect between the clothes Drake was rapping about and the clothes he actually wore. 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. 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.

As 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. He rapped that there wasn’t “a pair of Louis shoes [he] 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.”

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. 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.”

It wasn’t just fake Chanel wallets, however. In 2009, Drake famously wore a pair of Jordans that were almost immediately panned as “fakes” by the online sneaker community. Though eventually it was revealed the shoes were “customs,” wearing altered Jordans was still a serious misstep nonetheless. Still, the fashion foible was emblematic of the emcee’s style at the time: the shoes were Jordans, just not the Jordans.

During the mixtape years, Drake often stepped out wearing Jordans or, oddly enough, Redwing boots (more on that shortly). 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.”

Even 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. 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. His 2010 wardrobe still consisted of a steady diet of PLAY Comme des Garçons, ill-fitting leather jackets, baggy denim and plenty of Redwings. 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.

2011 was a big year for Drake. Rumours began that he was dating Rihanna—a now on-again/off-again relationship central to Drake lore. He dropped Take Care, the crossover smash that was both critically acclaimed and solidified that whether you him or not, Drake was a superstar. Lastly, he finally figured out how to dress himself.

Take Care contained just as few fashion references as Thank Me Later. Save for some bragging about jewelry on “Lord Knows,” Drake for once let his outfits—rather than his bars—do the talking. The most memorable style moment from Take Care is no doubt the music video for “The Motto,” in which Drake rides around in a convertible wearing the coveted Supreme x The North Face puffer and Nike football gloves. Apart from dabbling in streetwear, during 2011 Drake began dressing like a ‘90s hip-hop star, wearing baggy sweaters, half-open Versace silk button-downs, a bevy of gold jewelry and lightly tinted glasses. That year Vulture even penned an in-depth look at “The Many Sweaters of Drake”, highlighting his love of the garment. Between the chunky knits and the sharp tailoring he donned for GQ South Africa and awards shows, Drake seemingly embraced his role as the anti-rapper rapper early. Still, though, there were growing pains, and most of his style choices throughout the year are largely forgettable—”The Motto” perhaps the sole exception. As 2011 bled into 2012, Drake continued to fashion himself as a clean cut, throwback music star, gracing the cover of GQ for its April 2012 “Style Bible” issue.

Even Drake’s fans agreed that his style was nothing worth bragging about. During peak forum era, the rappers style was ravaged on Kanye To The, with comments ranging from, "I agree Drake is one of the worst dressed rappers...people on twitter say he dresses like a Cuban drug lord,” and “ most of his outfits are wack though” to simply “for real though Drake has the worst fits.” The consensus was not positive.

The next year was a period of transition. The vintage element was still present, with Drake regularly breaking out vintage Coogi throughout 2013. Throwback sweaters aside, more contemporary New York street fashion became a part of his wardrobe, with custom Hood by Air tops, lots of red leather jackets and a healthy rotation of Jordans and Timberlands. While remnants of luxury name dropping remained with his next release, Nothing Was the Same, with references to Tom Ford and high-end shopping malls, now that the rapper could actually afford to buy the things he boasted about, he moved on from the faux pas of the “Redwing Boot Gang.” By the end of 2013, Drake signed a deal with Jordan Brand, a partnership that not only dictated his footwear choices, but elevated him to the level of his rap mogul peers. Suddenly, Jordans were recurring theme in his music, most notably on “10 Bands,” where he brags about getting boxes for free.

Drake’s most noteworthy style choice in 2013 was his sudden fascination with white pants. He wore them with white Timbs, with satin shirts, with a black T-shirt, in another GQ spread—with anything really. One of the first instances of Drake experimenting outside the established hip-hop style cannon, the white pants proved Drake was suddenly more than a Northern foreigner emulating rap icons. Finally, he was Drake, a rap superstar, and he could wear white pants if he damn well pleased.

As Drake’s star grew throughout the mid-2010s, he gravitated towards sportswear—Baseball jerseys in particular, which he rocked on a number of occasions and released as part of OVO merch collections. His collegiate athlete vibe, eventually bled from his personal wardrobe to his business interests, the basis for the OVO clothing label. Originally simply tour merch, the OVO brand became a full-fledged streetwear label following series of traveling pop-up shops and co-signs from premium boutiques like Paris’ Colette. Yet, having personally covered the launch of the OVO x Roots collection at Colette in 2014, Drake still seemed less comfortable than, say, Pharrell or Virgil Abloh, amongst the fashion set.

When If You’re Reading This It’s Too Late surprisingly dropped in 2015, Drake’s style mimicked the emcee’s angry musical tone. Upset at the lack of respect and recognition for someone who ruled the charts as he did, blacked out fits became a Drake staple. While he continued to rep Supreme and Palace on occasion, more and more often Drake repped OVO head-to-toe, acting as a billboard while sitting courtside at Raptors games.

The all-black looks and steady rotation of OVO gear were central to Drake’s rebrand—from most hated to undeniable great. More than simply emblematic of his nonchalant jet-setting lifestyle, Drake’s style blended in with the larger trends within streetwear at the time. Today’s Drake, however—the most streamed artist on the planet—is a global phenomenon, with style to match.

After being introduced to Stone Island through the U.K.’s grime scene, Drake went full-on Stoney fanboy between 2016-2017. Not only did he wear the brand regularly, but he frequently wore multiple pieces at one, occasionally even matching pants and tops. He flaunted the brand’s iconic compass badge, commissioned Ben Baller to make a compass chain, and wore Stone Island for every stop of his U.K. tour. The logo-heavy high fashion turn made since—after all, on “6PM In New York”, the last track on If You’re Reading This It’s Too Late, Drake raps that he’s “head to toe Prada covered.”

On 2016’s Views, he shares some valuable insight, rapping “all of my dudes ain’t off rocking Gucci, one of them do it, we all gotta do it.” The insight doesn’t refer to his interest in designer fashion, but rather to the OVO clique’s group mentality. The grime rappers he became close with in 2016 and 2017 were all devoted Stone Island fans, so Drake became a devoted Stone Island fan. Clearly, like many of us, Drake’s style is reflective not only of current trends, but those he surrounds himself with. While Drake never claimed to discover Stone Island, he no doubt was a crucial component in the brands surging popularity in 2017 and early-2018.

Music mirroring life, Drake actually dripped in Prada when he signed a deal that saw him wear custom Prada outfits for the entirety of The Boy Meets World tour. While this was before Prada’s Fall/Winter 2018 show in January that set the fashion world on fire, the brand was already in the midst of a massive hot streak. Again, it was an instance of Drake wearing the right thing at the right time, but not necessarily a acting as a trendsetter—the exception being the reflective Linea Rossa parka he wore before the line’s official relaunch.

But mixed in between moments of clear endorsement and brand loyalty, Drake has become more discerning with his fashion choices. Rather than stick with main line Stone Island, he has experimented with Shadow Project—Errolson Hugh’s experimental tech-heavy line—and even vintage Stone Island courtesy of archivist Arco Maher. He even dove deeper into the techwear pool, wearing one of Hugh’s Acronym jackets on at least one occasion. Apart from Stoney, even nascent brands, like Montreal-based Hobby Wares, have found their way into the rapper’s rotation, a sign that Drake has realized that style is not necessarily synonymous with designer labels.

By the time we’re into 2018, Drake’s OVO imprint had already established itself as a Jordan Brand collaborator. Sure, Nike and Drake hadn’t necessarily churned out “break the internet”-level sneakers, but the pair had a steady relationship—with Drake regularly wearing Nike products on stage and off duty.

Even still, fans couldn’t shake the feeling that Jordan Brand was taking Drake for granted. The pair had dropped a few crisp versions of the Jordan VIII and Jordan X, but a never-to-be-released Jordan IV collab (known as the OVO x Jordan IV “Splatter”) and scrapped Jordan XIV collab left fans wondering: Were Drake and Jordan Brand drifting apart?

These rumors weren’t helped by the fact that Drake began appearing in public wearing various adidas gear—a pair of adidas trackpants here, a pair of Yeezys there—as whispers swirled across several media outlets that a Drake defection was imminent.

Enter Pusha-T.

While the public was expecting an announcement from the OVO camp on Drake’s forthcoming adidas deal, Drake dropped “Duppy Freestyle”. The move exacerbated a long-running feud between Kanye West, Pusha-T and Drake, with Drake directly responding to a ghostwriting diss from Pusha-T from the song “Infrared”. Pusha-T responded in kind, dropping “The Story of Adidon”. Personal attacks aside, the response revealed two key details. First and foremost, Drake was a father. Second, Drake was planning on dovetailing the public reveal of his son, Adonis, with the announcement of his adidas partnership.

While the personal life revelations ultimately became the bigger headline, Pusha-T’s line, “Adonis is your son, and he deserves more than an adidas press run”, became the closest to an “official” confirmation of Drake’s adidas deal the public would ever get. Now in a full-on cold war with adidas’ biggest hip-hop partners, it was clear that the OVO owl wouldn’t be touching anything bearing the Three Stripes.

No longer donning any adidas gear personally, a public appearance at Wimbledon in Summer 2018 confirmed that Drake was beginning to repair his ties with the team at Beaverton, wearing “Triple White” Air Max 97s. A pair of “For Stage Use” Air Max Plus sneakers proved that Drake was committed to the Swoosh. All that was left to do was confirm it through the music.

By now, we’ve all heard Travis Scott’s “Sicko Mode”, with Drake plainly declaring his allegiance; “checks over stripes”, made it clear which logo Drake was wearing going forward. With a feature on French Montana’s “No Stylist” asking girls to, “don’t wear no 350s round me”, Drake’s adidas deal was obviously dust in the wind.

By the time Drake's beloved Toronto Raptors were putting the Milwaukee Bucks on the ropes en route to the 2019 NBA finals, Drake was celebrating in a then-recently released Supreme x Nike collaboration sweatsuit.

While his Certified Lover Boy merch wouldn’t arrive until 2020, the fact that the merch was crafted in collaboration with Nike (featuring the Swoosh prominently on several pieces) leaves us thinking that Drake’s dalliance with adidas was just a metaphorical bump in road for OVO’s relationship with Nike. (This is to say nothing of the “Laugh Now, Cry Later” video—shot entirely at the Nike Campus in Oregon).

While Drake was cementing his relationship with Nike, he was also adding pieces to his thoroughly stocked designer wardrobe.

The most obvious addition is Tom Ford, with stylist Mellany Sanchez explaining to Vogue, “For Drake, Tom Ford has become a second skin. It is a brand he wears more often than he wears sportswear, more often than he wears anything else. It is a brand that he lives in.” It’s fitting (pun not intended), that Drake scooped up the award for “Best Rap Song” at the 2019 Grammys in a custom Tom Ford suit.

Of course that’s not the most ostentatious form of tailoring that Drake’s donned in this period. Sure, it’s not a shock that someone of Drake’s fame and monetary status would have access to top-tier custom tailoring. Drake, however, took things to the next level, scoring custom suits (down the branding itself) from Brioni. This sartorial flex was captured best in a Youtube video interview following a Drake performance at the O2 Arena in London. Breaking down how much his outfit cost, the $11,000 custom Brioni jacket is only the tip of the iceberg in a fit that totaled (with jewelry) up to nearly $1 million.

On stage, Drake has been a big supporter of fellow Nike collaborator Virgil Abloh and his work at Louis Vuitton, wearing various vests bearing the maison’s signature monogram. Abloh looks at Drake as a prophet of, and creative canvas for, his new vision of Vuitton, telling Vogue, “Drake is the pinnacle of contemporary artists and has the skill set to create an environment fulfilled by his set design. These characteristics support a perfect palette to create compelling new men’s silhouettes.” Even when he’s not on stage, you can spot Drake supporting Louis Vuitton; when Spotify served up an award to commemorate the smash hit “In My Feelings”’s 1 billion stream milestone, Drake ate pasta out of the plaque—all while wearing a denim jacket from the NIGO co-designed LV² collaboration.

Custom suits and new designer collections aside, you have to wonder if Drake’s been browsing the feed here on Grailed. From late 2019 and well into 2020, Drake was seen in various Chrome Hearts pieces pulled from years past, clearly developing a taste for the luxury, Biker-inspired label. With a history in releasing clothing on its own timetable, Chrome Hearts pieces are expensive because of the brand’s attention to detail, but a favorite on the secondary market for their exclusivity and rarity. His custom Chrome Hearts basketball jersey in the “Laugh Now, Cry Later” video (which, frankly, also served as a love letter to Nike) means that Drake might have an “in” at the L.A.-based brand.

Of course, Drake’s most “archive fashion” moment is clearly his appearance in the video for 2020's, “Toosie Slide”. While several outlets poked fun at his ostentatious penthouse apartment, we couldn’t overlook the fact that Drake commands the video while wearing a Raf Simons Fall/Winter 2001 “Riot Riot Riot” bomber jacket. Consistently standing as one of the most expensive items sold on Grailed, it’s not just that the piece is a significant piece of fashion history (or even significantly expensive)—it’s honestly one of the most coveted pieces across the style spectrum. Drake may have deleted the official music video-meets-house tour, but the moment stands as a major high point in Drake’s style history.

All that said, even as Drake’s interest in style—and fans’ interest in his style—has grown, fashion references have remained relatively scarce in his lyrics. When he does drop brand names, they tend to revolve around the wardrobes of the women he’s seeing. On Scorpion, Drake makes his feelings clear, rapping “Fashion week is more your thing than mine.”

Looking at both his career and his style trajectory over the past decade, it’s hard to argue with Drake’s self-assessment. He has never been a particularly “fashionable” guy. He has had his moments, sure, but, on the whole, he tends to adhere to an aesthetic put forth by others—whether that be Pharrell’s pop-prep-streetwear in his mixtape years or the Stone Island-wearing roadman look championed by grime’s superstars. Rather than a trendsetter, Drake—like many—learned from his predecessors and peers, eventually taking personal risks and developing a style that while culturally relevant, remains his own.