We’ll be the first to admit it, Drake’s personal style has not always been something to write home about. During his early years in the spotlight, he wore some head scratching choices for sure. But over the years, as he’s grown into arguably the biggest rapper in the world, his style has evolved with him and he’s found his lane in the style realm.

He isn’t always drenched in rare streetwear and sneakers like Travis Scott. He can’t wear whatever he wants and get away with it like ASAP Rocky, or pull of neon colors like Tyler, the Creator. He takes a much more subtle approach. Stone Island tracksuits, retro Nike sportswear, and custom tailored suits have all become staples in the 33-year-old’s wardrobe. Statement pieces are peppered in from time to time as well like vintage outerwear, uncommon throwback jerseys, or valuable Supreme collabs. When he wants to rep his squad, expect some pieces from his OVO clothing label to also make an appearance.

October is Drake’s month. To celebrate, we decided to take a look at some of the head honcho of OVO’s best outfits over the years. From Stoney to Brioni, here are 15 of our favorites.

Anonymous Hallway

When: 2015

Sure, every year is pretty big for Drake, but 2015 seemed like an especially monumental one for the Toronto rapper. By September when this fit was posted by him on Instagram, he was in the middle of his infamous beef with Meek Mill, What a Time to be Alive had just released, and “Hotline Bling” was brewing into the mega hit it would become. Context of the timeframe aside, this is just a clean winter fit from Drake. Say what you want about his style, he’s always had a pretty stellar outerwear game. This red, green, and black vintage North Face Steep Tech is no exception. The fresh pair of Timberland boots complete the classic cold weather fit.

Anonymous Garage

 

 

 

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A post shared by champagnepapi (@champagnepapi) on Jun 8, 2016 at 1:01am PDT

When: 2016

One can argue that Drake made Juventus a lot of money by rocking this pink jersey from the Italian soccer club back in 2016. Forget about the “Drake Curse,” this is just a clean jersey. The matching rose-tinted shades, and Rolls Royce Phantom in the background, makes it a classic subtle flex.

“Views” Photoshoot

When: 2016

The build up to Drake’s fourth studio album Views in 2016 had hardcore and casual fans alike anticipating an undeniable classic body of work. To this day, some people feel that the album just didn’t live up to the hype. Others have grown to love the project, which featured standouts like “Controlla” and “U With Me?” No matter your opinion on the album, you can’t deny that the accompanying photography was fire. One of the best photos saw Drake out in the snow in a fur trench coat standing in front of his mansion, dog leash in hand, and beside his black Rolls Royce Phantom. Straight up don status from Drizzy on this one. 

Scotiabank Arena

When: 2016

Drake has had some of his best fashion moments when he’s sitting courtside cheering on his hometown squad, the Toronto Raptors. Drizzy wore this particular outfit whole attending Scotiabank Arena with his OVO compadre OB O’Brien rocking a green nylon Gucci jacket with a monogram print Gucci scarf to match. Was it a calculated homage to Juelz Santana? We don’t know for sure, but we’d like to think so. 

“Look Alive” Music Video

 

 

 

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A post shared by champagnepapi (@champagnepapi) on Jan 24, 2018 at 8:04pm PST

When: 2018

Drake loves to cosign up-and-coming rappers. He’s hopped on many tracks over the years, which has helped several artists like Migos, ILoveMakonnen, and Lil Baby. One of the most notable instances of this is his appearance on Blocboy JB’s 2018 hit “Look Alive.” In the official video for the single, Drake rotates between a handful of fits, but the highlight has got to be this one. Up top, the Polo NASA Jacket from 1994, a piece that has become a grail among many collectors. Of course he’s rocking some Stone Island cargo pants to complete the look. Just look at that badge. 

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A post shared by champagnepapi (@champagnepapi) on Jul 10, 2017 at 1:32pm PDT

When: 2017

Supreme’s Louis Vuitton collaboration that released in 2017 is undoubtedly one of the most monumental projects in the history of streetwear. Given the collaborators and its limited nature, it also fetches a hefty price tag on the resell market these days. Drake, obviously, already has his pieces secured though. Here he can be seen, wine glass in hand to keep it classy, rocking one of the better pieces from the Supreme x LV collection—the co-branded monogram print denim jacket. We aren’t sure what exactly this post is, but it doesn’t really deter from how good the jacket is. We’ll give him a pass this time. 

The Novo DTLA

When: 2019

“The petty king.” This is what Drake referred to himself as on the track “Omerta” released in June 2019 to celebrate the Toronto Raptors first NBA championship earlier this year. If you needed any proof, here you go. The ongoing Drake vs. Kanye West saga has been an interesting one to follow. There are many layers to it. Thanks to J. Prince, there’s probably a ton of stuff that will be left unsaid, but that’s neither here nor there. Drake is still ready to fire off some subtle shots when he feels like it. Here, he can be seen rocking a “Ye Must be Born Again” merch hoodie designed by Cactus Plant Flea Market this past September. Petty king, indeed. 

2018 Halloween Party

When: 2018

Yes, this is actually a Fabolous Halloween costume. No, that doesn’t make the nostalgic fit any less fire. Drake rolled up to this 2000s-themed party in 2018 giving a nod to someone he refers to as one of his biggest inspirations in rap. It was the exact fit worn by Loso in the “Trade it All Pt. 2” music video. The throwback Minneanapolis Lakers Kobe Bryant jersey, baggy white undershirt, Los Angeles Dodgers fitted cap, and a baby blue bandana over top. Nice. *Fabolous voice*

Empire Lounge (Atlanta)

Drake Razor Ramon
Image via Getty/Prince Williams

When: 2018

Hey yo! Drake was oozing with machismo when he stepped out in this vintage Razor Ramon T-shirt. Surely to be appreciated by wrestling fans, Ramon (Scott Hall) was among one of the most popular professional wrestlers throughout the ‘90s with stints in the WWF and WCW to boast about. The bold yellow and black all-over graphic T-shirt couldn’t have come from any other decade. It’s one of the more valuabe vintage wrestling shirts, too. There’s currently one listed on eBay for $360. The Adidas track pants and white Adidas Climacools on feet also represent a very short-lived stint repping the Three Stripes back in 2018. 

2017 Billboard Music Awards

Drake Billboard Awards
Image via Getty/Allen Berezovsky

When: 2017

Fact: Drake makes great music. Fact: Drake loves Stone Island. This picture accurately confirms both things. Drizzy attended the 2017 Billboard Music Awards in the all-white Stoney fit. Here he can be seen flexing with this record-setting 13 awards. Make sure to take note of the super crisp white Air Force 1s on foot as well. Shoutout to this super cozy award show fit.

“Top Boy” U.K. Premiere

Drake Top Boy
Image via Getty/Karwai Tang

When: 2019

Sure, Drake has some fashion misses under his belt. We all do. But whenever he decided to step out in a suit it’s usually a hit. His appearance at the U.K. premier for Netflix’s Top Boy this past September was no different. A classic black suit (likely some custom Brioni or Tom Ford, but cannot confirm), grey turtleneck underneath, and a diamond necklace to accessorize. *chef’s kiss*

2019 NBA Eastern Conference Semifinals

Drake Courtside
Image via Getty/Vaughn Ridley

When: 2019

Drizzy doesn’t mess around when it comes to the Scotiabank Arena courtside fits. For the 2019 Eastern Conference Semifinals, he pulled out a serious statement piece, a blue paisley Visvim Kerchief down jacket from the cult-favorite Japanese brands Fall/Winter 2012 collection. He kept the rest of the pieces subtle—a white T-shirt, light washed denim, white Nike Air Force 1, and a single diamond necklace for good measure. 

2019 NBA Eastern Conference Finals

Drake Courtside 1
Image via Getty/Ron Turenne/NBAE

When: 2019

Drake had an impressive run of courtside outfits throughout the Toronto Raptors 2019 NBA Playoff run. One of the standouts is this nod to Tupac he wore during Game Six of the Eastern Conference Finals, a custom “100 Miles” hoodie inspired by Pac’s character Birdie from 1994’s “Above the Rim.” While he didn’t tie a bandana around his head like the late rap legend, he stayed on brand with one tied around his neck. Drake provided his own twist on the hoodie by embroidering “Kawhi Me a River” on the back in bold white letters, a tribute to superstar Kawhi Leonard. “Ivory Snake” Nike Air Force 1s on feet are just an added bonus.

2019 NBA Finals

Drake Courtside 2
Image via Getty/Garrett Ellwood/NBAE

When: 2019

Two things we have been able to establish thus far, Drake loves the Toronto Raptors and he loves to be petty with his outfits. This fit from Game One of the 2019 NBA Finals between the Toronto Raptors and Golden State Warriors checks both boxes. Here he can be seen celebrating courtside in a throwback Dell Curry Raptors jersey. Dell is the father of Warriors point guard, Stephen Curry. The jersey choice set Twitter on fire that night. Dell and wife Sonya were even impressed at the rapper’s choice. No “Drake Curse” on display here either. The Raptors won the game 118-109. Drake is playing chess with his fits. We’re all just playing checkers. 

Los Angeles

Drake Finesse
Image via Getty/Hollywood To You/Star Max

When: 2019

This is one of Drake’s outfits that had the internet searching for a way to acquire it for themselves back in July 2018. Perhaps inspired by his Scorpion cut “Finesse,” he stepped out in a bright orange University of Tennessee crewneck with the letters meticulously carved out to read “Finesse” instead. The piece was designed by lowkey brand icantdecideyet who surely appreciated the buzz brought forth by the monumental cosign. As he is known to do, Drake kept it cozy with a pair of black nylon track pants and matching Nike Air Max Plus sneakers to complete the casual Los Angeles look.





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