December 24th, 2009
Best of 2009, Men's style
Undercover Fly Guy of 2009: Drake
By Claire

With all the buzz and hoopla this year around Kanye’s outbursts and Tiger Woods’ “transgressions,” did we even take the time to look at one of the best up and coming rap artists in the game?   Aside from his number 1 singles, who would’ve thought Drake would have a closet worth envying?

Drake 1
Gone are the days of gangsta rap with matching attire, i.e. baggy jeans and oversized hoodies.  Drake likes to keep things casual with patterned shirts and understated, yet dope footwear.

Drake 5

Drake 8
A prepster at heart, Drake loves his cardigans and pullovers. The Comme des Garcons sweater adds some unexpected flair to his ‘fit.
Drake jackets

He also likes to keep things simple with both leather and denim jackets and manages to make a pair of khakis look comfortable with a pair of Air Yeezy’s.

Drake suits 1
When the occasion calls for it he cleans up nicely usually keeping it classic when it comes to suits with shades of black and gray.  But unlike a lot of people, he manages to not look pretentious and forced into a suit.  Effortlessly fly is the name of his game.
Drake 2

What do you guys think of this year’s undercover fly guy?
Check out a few hits:

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16 Responses to “Undercover Fly Guy of 2009: Drake”

  1. Miss Kellie says:

    Luv him!

  2. Evana 2 Cute says:

    Yeah he has a nice Swag!!!

  3. AD says:

    Great profile and really great style. Love ya Drizzy!

  4. divasoul says:

    good choice! he looks great.

  5. Les says:

    I agree, love his style.

  6. DeirdreDawn says:

    sorry but i have to disagree i always thought Drake should fire his stylist. I feel he doesnt have an edge…. im just saying but his GQ party grey suit was pretty Haute

  7. brie says:

    my mannn :D
    i love him!

  8. Nuru says:

    Loves it, thank you Vuitton for giving Drake the title of undercover fly guy of the year. Some people may argue that he has no edge, but it is the classic nature of his style with the swag that he so effortlessly exudes that makes him THAT guy. From the moment I watched Replacement Girl, best believe I KNEW this dude was repping that T. Dot to the fullest.

  9. LoudPen says:

    I loves Drake! I wasn’t excited when I first heard about him b/c it seemed like he was all hype, but, then I actually took the time out to listen to his music and he is hot ish! Plus he has some definite style & swagger. Also, I don’t get the statement that he has no edge. He looks like a fashionable regular guy…just b/c he’s a celeb doesn’t mean he needs to wear things just to be a trendsetter. He can look nice & not always have to be over the top. Plus, that over the top style doesn’t seem to fit his personality.

  10. Kee says:

    Drake is hot ish…..You wouldn’t think that this man could rep the mic as well as he does. Just goes to show that when you have talent, the talent speaks for itself not the looks.

    Merry Crimus E’rybody!!!

  11. JIhan s. says:

    Those pictures are gorgeous!

  12. JennyMiranda says:

    I like Drake, still trying to access his style however.

  13. StarBaby says:

    I think Drake’s sense of fashion is refreshing right now. I can’t express enough how sick I am of guys in jeans tighter than a female’s and those same jeans sagging (pick a lane). Or the “Saved by the Bell” colored shirts (New Boyz). I love a dude than can manage to stick out with casual wear in a good way and know how to dress for the occasion (Did you see what Wale wore to this year’s GQ dinner? Booo! The hood ain’t for everywhere.)

  14. niall barry says:

    drizzy is the flyest mo fo in the game

  15. [...] Drake The GQ Man of the Year upped his chic quotient significantly this year, going for an undercover fly guy of 2009 to to a certified style star. Instead of his typical jeans, cardigans, and varsity jackets, he [...]

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