Drake's Most Stylish On-Stage Moments

Image via Complex Original

Date: August 5, 2012

It's no wonder Drake really tried to pass the pauseworthy "Young Angel" off as a moniker, because dude can't miss when he opts for pearly white. OVO owl colors were practically made to match with Jordans like the Golden Moment pack, which he favored every now and then in 2012. Is this where talks for official OVO Js began?

Date: Grammy Awards, February 13, 2011

That leather bomber is too fire, but with stage lights, actual flame, and most importantly, Rihanna, in that outfit, shaking right next to him? You just know your boy Aubrey was perspiring something fierce.

Date: April 2010

Now there's something to write home about. Early-Drake's style risks held a pretty even ratio of hits to misses, but on his first headlining tour, he came correct with this Supreme M-51 cheetah print field jacket. It's not the last time he'd stunt in a Supreme animal-print joint either. 

Date: August 2, 2010

This is probably the first piece of October's Very Own gear that let everyone know Drake and co. were about to bring it with their merch game. It was appropriately worn at the inaugural OVO Fest.

Date: June 1, 2014

The night of Hot 97's annual Summer Jam was a good one for Drizzy before he even fulfilled his assumed cameo appearance, mostly because he dropped a monster by the name of "0-100" during the show and thugged everyone for their shine. When he finally joined Nicki, along with Wayne, he stunted on everyone once more with a pair of rare Jordan Oregon Ducks IVs. Dope sweater, too.

Date: July 23, 2014

Drake's big ESPY host gig was more or less a success, and he didn't embarrass himself on the style front either, except for when failing miserably was the actual intent (see: Russell Westbrook "costume") and this unfortunate beach resort getup. As every host should, he executed several costume changes going from formal wear to theme-appropriate jerseys. The illest look of the night hands down was this black-and-white OVO jersey (complete with trademark owl on the collar) that we can only pray becomes available to the non YMCMB/OVO/OMO/SZN public soon.

Date: August 25, 2013

As far as the rap game is concerned, 2013 was Drake's year, and by VMAs time, everyone knew it including the man himself. So of course when it came time to perform a medley of "Hold On, We're Going Home" and the then, still-commanding "Started From the Bottom," he strode out cockier than ever in a strong all-black look, while the rest of his team posted in Nothing Was the Same promo tees and baseball jerseys.

Date: June 7, 2010

Here Drake's once again falling back on the Early-Aubrey denim-and-chino uniform, but what elevates this look from meh to 100 real quick is A) The Free Lil Wayne shirt, because Drake is a loyal protege, and B) Early shades of footwear flaunting with those crisp Do the Right Thing Jordan IIIs. Too clean.

Date: November 2013

Capsule one of Drizzy's Calvin Klein-designed "Would You Like a Tour?" alphet is all blue sky-themed to match the Nothing Was the Same artwork. Appropriately, Drake's floating 30,000 feet in the air above the haters with this strong look.

Date: August 5, 2013

For the tour de force OVO Fest IV, easily the best to date and one of the best rap shows in recent history, Drake fell back into his Young Angel wave with a full cokeboy look, completed with a very on-trend baseball jersey.

Date: October 2013

Calvin Klein really hooked Champagne up with the comfiest-looking tour uniform ever. He may as well be in pajamas inviting you to a tour of his actual crib.

Date: August 2013

During Big Sean's Hall of Fame show Drake held it down for the hometown hero with a surprise performance of their banger "All Me," decked out in one of his highly favored OVO "Welcome to the Family" Cash Money tees.

Date: November 2010

Simple, clean, effective. Staying true to those three factors was kind of a big deal for pre-2013 Drake.

Date: March 2010

It seems like Drake throws jabs at the Throne every chance he gets these days, but his history of cockily bucking the hierarchy actually goes back to his early days in the game. During a Madison Square Garden stop on Jay Z's Blueprint 3 Tour, co-headliner Jeezy brought YMCMB in the house for a show-stopping cameo performance of "I'm Goin In." As you'll remember, Hov was heavy on the all-black-everything wave around this time, as per "Run This Town," going so far as to stick to it unwaveringly for the tour and enforce the same dress code for guests. Welp, while Lil Wayne and Nicki Minaj adhered, Drake—at the time still trying to make the regrettable nickname "Young Angel" happen— brazenly showed up in an all-white, coked-out get-up. Harmless yet winking, it was nonetheless a move that foreshadowed his increasing lack of deference.

Date: June 7, 2009

Drake's first Summer Jam appearance, courtesy of Young Jeezy, wasn't quite as triumphant as his stage appearances are now. For one thing, his style was a little wayward, even if we're grading on a "appropriate-by-2009-standards" curve. The denim jacket and pullover hoody look drove his every-man, relatable theme home a little too hard, as if he was performing in his friend's backyard instead of one of the biggest rap shows of any given year. Thankfully, Air Yeezys on his feet made the cypher complete.

Date: February 20, 2010

Drake's style game was very off-and-on before he finally got it together last year, but one of his layup looks when he first hit the scene in 2009-2010 was a classic, can't-miss denim shirt/jacket and chino pairing. Did he resort to it too often? Yes, but there were plenty of times back in those days when he didn't and we all suffered for it.