When Drake appeared on the scene in 2009, he became an instant rap/R&B heartthrob with his EP 'So Far Gone,' which boasted the hit single, 'Best I Ever Had.' Since then, the Toronto rapper-crooner has evolved not only with his music but with his clothing style as well.

The OVO leader has grown from just wearing sweaters and jeans to rocking dress shirts and Tom Ford suits. However, the 27-year-old crooner has made some questionable fashion choices. Earlier this year, he appeared in DJ Khaled's 'No New Friends' music video wearing a DADA Supreme leather jump suit and Timberland boots. That didn't turn out too well. But at least he took the online slander in good jest.

For our style evolution profile, we examine 10 of the Young Money superstar's best looks and missteps through the years. Check out Drake's Style Evolution below.

  • Collegiate & Casual

    Frazer Harrison, Getty Images

    When Drake dropped 'So Far Gone' in 2009, his style of dress was more collegiate and very causal. During his first appearance at the BET Awards, the Toronto native rocked distressed jeans, boots and a cardigan sweater from Comme des Garcons PLAY, which don’t come cheap. Even then, Drizzy had a taste for designer threads.

  • Suited Up

    Frederick M. Brown, Getty Images

    Before Jay Z rapped about it in a song featured on 'Magna Carta Holy Grail,' Drake was rocking Tom Ford. At the 2010 MTV Video Music Awards, the OVO mastermind donned a black suit designed by Mr. Ford. He keeps it extra fly with purple velvet loafers decorated with red tassels. Very classy, Aubrey.

  • Champagne Papi

    Michael Loccisano, Getty Images

    Perhaps inspired by the 1977 dance flick 'Saturday Night Fever,' Drake opted for the guido look while attending the 2011 Songwriters Hall of Fame event. In some sartorial circles, wearing a tank top with a suit is a fashion no-no. Plus, with a bit of his chest hair showing and a silver necklace for flair, it makes him look like an extra on 'A Night at the Roxbury.' Cue Haddaway’s song 'What Is Love.'

  • Black on Black

    Ethan Miller, Getty Images

    In 2012, Drake kicked off his first headlining excursion called the Club Paradise Tour. Unlike other superstar artists who like to wear flashy gear onstage, Drizzy opts to keep everything basic… and black. The 27-year-old rapper’s touring attire is usually a black T-shirt (the oh-so soft cotton tees by Ralph Lauren), black jeans and boots (above he’s wearing the classic Timberland field boot). When you're onstage for two hours rocking the mic, cozy is best.

  • Pajama Clothes?

    Frederick M. Brown, Getty Images

    Although he won a Moonman at the 2012 MTV Video Music Awards, some frowned on his outfit of choice. For the occasion, Drake wore a tie-dye-inspired V-neck top from Alexander McQueen and paired it with black trousers and black tasseled loafers. Considering that A$AP Rocky and others dressed in high-fashion gear, the rapper’s attire shouldn’t have raised eyebrows. Nonetheless, we wonder if Kendrick Lamar was talking about this outfit during his BET cypher verse -- "Nothing's been the same since they dropped 'Control' / And tucked the sensitive rapper back in his pajama clothes."

  • Tom Ford All-Star

    Jason Merritt, Getty Images

    Every man looks good in a tuxedo and the same can be said for Drake. At the 2013 Grammy Awards, the Young Money superstar turned heads with a navy-and-black tuxedo designed by Tom Ford. Drizzy did everything right with this outfit. He even kept the accessories to a minimum -- a gold watch (possibly Rolex) and a matching gold bracelet. On top of that, he also won the Best Rap Album trophy for 'Take Care.' Bravo.

  • Sweater Is Better

    Valerie Macon

    The Toronto native is also known for his love of knitted sweaters (peep his 'Headlines' video). Here, he keeps it basic with a cable-knit red sweater. He's been spotted wearing throwback Coogi sweaters to shawl-collared crewneck sweaters too. We can’t blame him for rocking gear that keeps him warm, it gets cold in Canada. But does he do it better than Bill Cosby? You be the judge.

  • Silky Does It

    Robin Marchant, Getty Images

    Although he’s known for his sweaters, Drake can also dress up in silk shirts and pair them with selvedge denim. The debonair singer-rapper looks mighty cool in a pattern dress shirt with black jeans. He accentuates the ensemble with a gold watch, OVO owl necklace and square-shaped sunglasses. This outfit reminds us of his suave but heroic turn in the 'Hold On We’re Going Home' video. Miami nice, indeed.

  • Nothing Was the Same

    Jamie McCarthy, Getty Images

    After getting teased about his wardrobe at the 2012 MTV Video Music Awards, he decided to keep everything neutral and go all black this year. Plus, he had an album, 'Nothing Was the Same,' to promote. So what better way to advertise your product than to make yourself a walking billboard. Here, Drake dons a black baseball jersey, zippered cargo pants and charcoal-colored Timberland boots. All-black everything is always in style.

  • Don Dada

    Drake wearing a throwback leather Dada short suit and Timberland boots generated one of the most hilarious online memes, arguably, in Internet history. First of all, props to Drizzy for even finding a Dada suit in 2013. The rapper’s fashion misstep was photoshopped on hundreds of images and posted on Instagram, Tumblr and Twitter. Our favorite is the 'Soul Train' line dance and the old lady "Life Call" gif. Thankfully, Drake took the slander in stride and posted a couple of his favorite images on his Instagram page. All praises due to the Don Dada!

  • October's Very Own

    David Becker, Getty Images

    By now, everyone should understand that Drake is a hip-hop superstar who is idolized by everyone, including Will Smith’s son, Jaden. At the 2013, iHeartRadio Music Festival, the rapper-crooner appeared wearing a long-sleeved OVO T-shirt that featured an image of Jaden’s face. The shot of the young entertainer in awe comes from the 2013 MTV Video Music Awards, where this facial expression came as a result of watching Drizzy’s performance. It's insane to think that Jaden looks at Drake in such high regard, considering who his father is and his legacy in the rap game. Sadly, this shirt is a one-of-one.