Drake's 50 Best Outfits

When: 2011
Where: Juno Awards

As the show's host, it was only right for Drake to look as dapper as possible at the 2011 Juno Awards in a classic bowtie and tux combo.

When: 2010
Where: MTV Video Music Awards

Oh you fancy, huh? Drake hit the VMA red carpet in a Tom Ford suit and pink-tassled velvet slippers before performing the fitting "Fancy."

When: 2012
Where: "HYFR" video

What better place to recommit to the Jewish faith than by having a re-bar mitzvah at your music video shoot? "HYFR" got everyone in the celebration spirit. Peep Birdman and Khaled rocking yalmulkes was the style conversion of the year.

When: 2010
Where: Los Angeles

The OVO varsity jacket was rocked by the whole crew in 2010 but became so popular that fans started wearing them too. Talk about Crew Love.

When: 2010
Where: Vancouver airport

Last night must've been mad real... Drake hid his peepers while traveling in a full cozy boy get-up.

When: Unknown
Where: Unknown

Meow! Drake's Gitman Bros. Leopard Head Oxford shirt is a nice play on the leopard print that Drizzy is usually such a fan of.

When: 2011
Where: "Headlines" video

"Headlines" was one of the first highly-publicized appearances of Drake's beloved Cosby sweater. He'd later admit to NY Mag that he owns over 1,000 sweaters. "I love sweaters...I don't know, that's honestly my favorite clothing item." 

When: 2010
Where: GQ

Drake was GQ's Breakout Man of 2010. This manly look included a military coat by Burberry Prorsum, a sweater by Zadig & Voltaire, and boots by Nice Collective.

When: 2013
Where: XXL magazine

Drake offset a camo jacket with a real life owl for his XXL photoshoot. An OVO shoutout or maybe a homage to Aaliyah's "Are You That Somebody" music video, the wildlife look is good on him.

When: 2009
Where: BET Awards

Drake loves both sweaters and high-end designers, so it only makes sense that he'd put the Commes des Garcons red heart emblem on his chest.

When: 2013
Where: NYC

This look was supposed to be part of Drake shooting the new "Anchorman 2" movie with Judd Apatow, but he took to the throwback look quite well.

When: 2013
Where: OVO Fest, Toronto

Drake knows how to pull off the risky mixing of prints with this ensemble worn after OVO Fest. Block horizontal stripeed baseball jersey and OVO tribal print together? Yup. He did it.

When: 2012
Where: "Started From the Bottom" video

White Bentley, white fur, white Canadian snow. The "Started From The Bottom" music video clearly had a theme in this scene.

When: 2010
Where: VMAs

Drake loves putting his song and album titles on his shirts. This TLC shirt was apt, given that Drizzy re-made the group's "Fan Mail."

When: 2012
Where: Toronto

When the temps really drop, Drizzy's Canadian roots come out. No better way to deal with sub-zero temps than with a Patagonia down jacket.

When: 2010
Where: Complex cover

Drake's first Complex cover was a true mix of high and low fashion. Drizzy was laced in everything from a $396 Burberry bomber to a $40 J. Crew henley. 

When: Unknown
Where: Unknown

Even at a young age, Aubrey was styling. His suit, sweater and tie combo is school picture-ready.

When: 2012
Where: Unknown airport

In his white tee, Drake keeps it simple and clean. He lets the PJ in the background speak for him.

When: 2011
Where: Miami

Drake brought out his best Tom Ford duds to celebrate Lil Wayne's Welcome Home Party in Miami. "I'm here to have fun and celebrate a great, phenomenal, legendary man. That's why I had to get dressed up," he told MTV. Weezy would be proud.

When: 2009
Where: NYC

Drake played his first sold-out show in NYC back in '09 wearing the Commes De Garcon PLAY stripe shirt offset by red Air Jordans. Dude really does wear his heart on his sleeve.

When: 2011
Where: Source magazine cover

Drake gave the term "gangsta grillz" new meaning when he graced the cover of The Source. The rapper took a big bite out of his OVO (October's Very Own) necklace while wearing the matching tee.

When: 2010
Where: Vibe cover

Most rappers rock Jesus pieces but Drake gave his first Vibe cover a unique spin by repping his Jewish heritage. His gleaming Chai necklace was the perfect piece to offset an otherwise minimal look.

When: 2013
Where: YOLO Estate

This look is quintessential Drake. Yellow shorts, Nike boots, and a Missoni sweater. Like the rapper himself, it shouldn't work but dammit, it does.

When: 2011
Where: Toronto

It's no secret that Drake loves Aaliyah (Just look at the big tattoo on his back for proof). If you still need proof, peep his kaleidoscope tee featuring the late singer, designed by Toronto based company Mango Peeler.

When: 2013
Where: Unknown studio

Drake rocking Wu Wear all made sense what "Wu-Tang Forever" was introduced to the world. 

When: 2011
Where: Bill Clinton fundraiser

Drake kept it real casual and streetwear-heavy at Bill Clinton's 2011 fundraiser with the Supreme Jungle Zebra jacket.

When: 2012
Where: Philly

Meek Mill had no problem partying shirtless, but Drake threw on his Jil Sander python print t-shirt for the occasion.

When: 2013
Where: Los Angeles

Everyone and their mama is rocking Hood by Air right now. Drake wore it earlier this year as he was kicking it with what was potentially his last "new friend," NBA superfan and fashion superstar James Goldstein.

When: 2013
Where: Backstage at Justin Bieber concert

Even though Drake proudly reps our neighbors up north, we appreciate the Dream Team sweatsuit he brought back.

When: 2011
Where: BET Awards

All black everything with yellow shoes? Just like his sound, you think you know where he's going with something and then he'll hit you with the surprise move out of nowhere.

When: 2005
Where: Degrassi Community School

If you watched "Degrassi," then you know that Jimmy Brooks was cozy boy before cozy boys knew about "cozy boy." Also, just peep his Luniz-inspired "I Got Five on It" T-shirt. High five, Jimmy.

When: 2010
Where: VH1 Hip Hop Honors

There's no doubt that Drake kept mentor Lil Wayne's name alive in the streets while Weezy was locked behind bars. The "Free Weezy" tee Drake wore on VH1 went for $20 but can now be purchased (ironically?) for a cool $7.99 at Hot Topic.

When: 2013
Where: MTV VMAs

This "Nothing Was the Same" baseball shirt may not have been the NWTS gear that started a fight in NYC, but it's some of the only artist merch that gets a heavy co-sign.

When: 2012
Where: Playboy Mansion

What do you wear to a mansion where you're surrounded by naked women? A Supreme hoodie, of course.

When: 2012
Where: Turks and Caicos

The tranquil waters of Turks and Caicos inspired this bright island look complete with rock climbing-ready kicks.

When: 2012
Where: VMA Awards

Drake won big at the 2012 MTV Video Music Awards, but it was his Alexander McQueen raven print sweater that we were all talking about well after the telecast. It takes a real man to show off the man cleave.

When: 2013
Where: Unknown

The shirt is loud, but keeping it simple in white denim and coke white Timbs makes this risky look work.

When: 2011
Where: NYC

What better way to ring in the frigid New Year in NYC than with Carson Daily and a custom OVO $5,000 jacket? The limited edition buffalo leather jacket featured a silk-lined interior and a detachable fox fur trim along with gold-plated hardware. Luxe.

When: 2013
Where: Grammy Awards

That boy clean up good. Drake looked dressed up just enough for the 2013 Grammy Awards in this Saint Laurent midnight shawl lapel tuxedo jacket and patent leather kicks.

When: 2012
Where: NHL All Star Game

Canada's version of a throwback jersey is, of course, related to hockey. Drizzy knows how to play to a crowd, and rocked this for the NHL All Star Game that took place in Ottawa, Canada.

When: 2013
Where: Unknown airport

Drake has spent most of this year reminding us that his album "Nothing Was The Same" drops September 24th. This Cross Colours jersey from god-only-knows-where might be the greatest promo tool ever.

When: 2012
Where: YOLO Estate

Smoking hookah and wearing fuschia velour, Drake captioned the plush look in this photo "Christian Grey" after the main character in '50 Shades of Grey.'

When: 2009
Where: GQ

Drake joined Wale and Cudi for GQ's "Gangsta Killers" features. Not sure what going to the laundromat has to do with gangstas or killers but Drake's fur-trimed bomber jacket and sweatpants combo certainly killed it.

When: 2013
Where: Toronto

The best way to show off a new Rolls Royce is dipped in Highland head-to-toe. Smart move, Drake. This is one of the few outfits that might distract people from the whip for a sec.

When: 2013
Where: MTV VMAs

If you're ever blessed enough to rock custom Alexander Wang, you know you've made it. 

When: 2013
Where: "No New Friends" video

The outfit that launched a thousand hilarious memes... When images leaked of Drake rocking the throwback line Damani Dada for the "No New Friends" video, '90s kids everywhere rejoiced just a little.

When: 2012
Where: Toronto

Winters in the Great White North are no joke and Drake's mink coat (estimated to cost $100k) looked like it could stave off any chill.

When: 2012
Where: "The Motto" video

Drake's Supreme x The North Face "Leopard" Nuptse Down Jacket in "The Motto" video goes for over $2,000 now on eBay, but you only live once, right? 

When: 2011
Where: Las Vegas

Drake stole "Versace" right from under Migos this year and you can see why. Drizzy loves rocking the Italian designer's baroque prints, including this blue silk shirt he wore in Las Vegas.

When: 2011
Where: Saturday Night Live

Drake's old man Bill Cosby sweaters have become a part of the rapper's calling card. No stranger to criticism, Drizzy poked fun at himself with some help from Andy Samberg on Saturday Night Live. Still, that Coogi knit is fire. Biggie will always be the innovator of this piece, but this piece is so emblematic of Drizzy that it had to grab the top spot.