2005(01 of41)
Open Image ModalDrake looking like he’s in desperate need of a tailor at the 2005 Teen Choice Awards. (credit:Getty)
2006(02 of41)
Open Image ModalDrake with his "Degrassi" buds, Shane Kippel and Adamo Ruggiero. We can’t really fault the kid here. He looks like a typical teenager wearing a baggy checkered shirt and jeans. (credit:Getty)
2007(03 of41)
Open Image ModalDrake looking Canadian in a parka and cozy black hoodie. (credit:Getty)
2007(04 of41)
Open Image ModalHmm, not half bad. Drake wears a black military-esque jacket at the Spring Awakening and “Degrassi” panel discussion with Rosie O'Donnell. (credit:Getty)
2007(05 of41)
Open Image ModalThe beginning of the sweater obsession. Drake looks casual in a black cardigan and jeans at MTV studios. (credit:Getty)
2009(06 of41)
Open Image ModalEither he started purchasing clothes that fit him properly or he just grew nicely into his body. Lose the Louis Vuitton change purse though Drake. No one likes a bragger. (credit:Getty)
2009(07 of41)
Open Image ModalWe’re really digging this sweater-Henley combination at the BET Awards. The heart melts our hearts Drake. (credit:Getty)
2009(08 of41)
Open Image ModalSlow clap for this impeccably tailored grey suit. Drake attends the GQ Man of the Year awards. (credit:Getty)
2009(09 of41)
Open Image Modal2009 seems to be the year of suave Drake, posing at the Grammy nominations concert in a velvet blazer with a silk pocket square. (credit:Getty)
2010(10 of41)
Open Image ModalBold but not the most flattering of coats. (credit:Getty)
2010(11 of41)
Open Image ModalDrake attends the 52nd Annual Grammy Awards in a pretty low-key outfit - leather jacket, dark grey tee-shirt and jeans. You can’t really go wrong with the classics. (credit:Getty)
2010(12 of41)
Open Image ModalDrake performs at the VH1 Hip Hop Honors wearing a shirt demanding the release of his mentor. We dig the denim jacket and khakis combination. (credit:Getty)
2010(13 of41)
Open Image ModalHoly green metallic blazer. This is definitely Drake’s colour at Lil Wayne’s welcome home party. (credit:Getty)
2010(14 of41)
Open Image ModalDrake embracing a classic no fuss suit at the Juno Awards. (credit:Getty)
2010(15 of41)
Open Image ModalBlack on black and then yellow? Not the best footwear choice. Drake brings up images of Big Bird’s feet at the BET Awards. (credit:Getty)
2011(16 of41)
Open Image ModalDrake looks low maintenance, wearing a military jacket and black denim at the launch of Google Music at Mr. Brainwash Studios. (credit:Getty)
2011(17 of41)
Open Image ModalDrake adds a casual element by forging the tie at a press conference in South Africa. (credit:Getty)
2011(18 of41)
Open Image ModalDrake literally looks 13 in this outfit as he performs as part of Wild 94.9's Wild Jam at HP Pavilion. We don’t approve of this get up. (credit:Getty)
2010(19 of41)
Open Image ModalDrake is all smiles in a warm bomber jacket at New Years Eve 2012 with Carson Daly. (credit:Getty)
2012(20 of41)
Open Image ModalDrake on stage at the 54th Annual Grammy’s in a classic tux. (credit:Getty)
2012(21 of41)
Open Image ModalProud Canadian Drake attends First Down Friday at Sensu wearing a sweater that can’t be denied. (credit:Getty)
2012(22 of41)
Open Image ModalDrake at the 2012 Budweiser Made In America Festival wearing an appropriately Bud blue bomber. We’re not sure we like the ensemble though. (credit:Getty)
2012(23 of41)
Open Image ModalDrake wears a form fitting Versace shirt at the 2012 MTV Video Awards. (credit:Getty)
2013(24 of41)
Open Image ModalDrake’s new 2013 look. Kidding! Drake films a scene for "Anchorman: The Legend Continues." (credit:Getty)
2013(25 of41)
Open Image ModalDrake looking like his usual dapper self at the 55th Annual Grammy Awards in a blue grey tuxedo blazer with black lapels. We love the detail on the side of his pants. (credit:Getty)
2013(26 of41)
Open Image ModalDrake’s best look yet at the Raptor’s press conference. (credit:Getty)
'Degrassi' Stars(27 of41)
Open Image ModalDrake as Jimmy Brooks and Shenae Grimes as Darcy Edwards. (credit:CATV / courtesy Everett Collectio)
The Cast Of "Degrassi: The Next Generation"(28 of41)
Open Image Modal (credit:CATV / courtesy Everett Collection)
Drake(29 of41)
Open Image ModalDrake looking fly at the Raptors press conference in Toronto. We dig the no socks look. (credit:Getty)
Drake(30 of41)
Open Image ModalDrake arrives at the 55th Annual Grammy Awards looking dapper in a bow tie and two-toned tuxedo blazer. (credit:Getty)
Drake(31 of41)
Open Image ModalDrake pops in red pants and chambray shirt at the Cash Money Records 4th annual pre-GRAMMY Awards party. (credit:Getty)
Shenae Grimes(32 of41)
Open Image ModalShenae Grimes looks rocker chic with a metallic blazer and studded black and gold heels at the 2013 “Teen Vogue” Young Hollywood Awards. (credit:Getty)
Shenae Grimes(33 of41)
Open Image ModalShenae Grimes rocks leather pants and a shimmery silver jacket to the 2013 Entertainment Weekly Pre-Emmy Party held at Fig & Olive Melrose Place. (credit:Getty)
Shenae Grimes(34 of41)
Open Image ModalComfy in Converse, actress Shenae Grimes attends the Skechers 'Summer Soiree' at SkyBar at the Mondrian Los Angeles. (credit:Getty)
Nina Dobrev(35 of41)
Open Image ModalActress Nina Dobrev attends Cosmopolitan's Summer Bash in a cheery yellow mini dress by Julien MacDonald. (credit:Getty)
Nina Dobrev(36 of41)
Open Image ModalNina Dobrev wears a form fitting blue Versace dress to The CW Network's New York 2013 Upfront Presentation. (credit:Getty Images)
Nina Dobrev(37 of41)
Open Image ModalNina Dobrev looks like a punk princess in this custom Monique Lhuillier gown. (credit:Getty)
Lauren Collins(38 of41)
Open Image ModalActress Lauren Collins attends the Second TIFF Dipnight After Party looking casual but chic in a leather jacket. (credit:Getty)
Cassie Steele(39 of41)
Open Image Modal“LA Complex” actress Cassie Steele looks equal parts rocker and boho chic in this outfit at the “Nylon” October IT issue celebration. (credit:Getty)
Cassie Steele(40 of41)
Open Image ModalCassie Steele attends the Chinese Laundry Fashion Denim launch party in a floral mini skirt and black crop top. (credit:Getty)
Cassie Steele(41 of41)
Open Image ModalCassie Steele makes a statement wearing bright red leather pants and a black Rolling Stone t-shirt to “Much Music” headquarters in 2012. (credit:Getty)