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look book
March 24, 2017

See 10 Years of Drake’s Coziest Looks From Timbs to Tom Ford

By Leah Rodriguez

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Photo: Kevin Winter/Getty Images

Drake has learned a few things about tailoring since he first came on the music scene in ill-fitting jeans, but it doesn’t seem like he’s going to stop wearing sunglasses indoors anytime soon. Thankfully, the world’s coziest celebrity might never let go of his deep appreciation of sweaters. This week the rapper released a “playlist,” full of Caribbean-inspired beats to match his Nancy Meyers–esque linens. If there’s one staple to Drake’s wardrobe it’s athletic jackets, ranging from leather biker styles to varsity silhouettes. See the Canadian in his best outerwear, Tom Ford tuxedo, and more in our slideshow ahead.

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1 / 53 Photos
April 17, 2018 At a game between the Washington Wizards and the Toronto Raptors in Toronto. Photo: Ron Turenne/NBAE/Getty Images
March 4, 2018 At the Vanity Fair Oscar Party in Beverly Hills. Photo: Kevin Mazur/VF18/WireImage
October 21, 2017 At an NBA game between the Philadelphia 76ers and the Toronto Raptors in Toronto. Photo: Vaughn Ridley/Getty Images
September 9, 2017 At 'The Carter Effect' premiere during the Toronto International Film Festival. Photo: George Pimentel/WireImage
June 26, 2017 At the NBA Awards in New York City. Photo: Taylor Hill/FilmMagic
May 20, 2017 Performing during the Billboard Music Awards. Photo: Ethan Miller/Getty Images for dcp
May 21, 2017 At the Billboard Music Awards. Photo: Chris Polk/BBMA2017/Getty Images for DCP
November 20, 2016 Where: On stage at the 2016 American Music Awards in Los Angeles. Photo: 2016 Getty Images
November 16, 2016 Where: At a Golden State Warriors and Toronto Raptors game in Toronto. Photo: 2016 Getty Images
May 23, 2016 Where: At game four of the Eastern Conference Finals between the Cleveland Caveliers and theToronto Raptors in Toronto. Photo: 2016... May 23, 2016 Where: At game four of the Eastern Conference Finals between the Cleveland Caveliers and theToronto Raptors in Toronto. Photo: 2016 Getty Images
February 14, 2016 Where: On stage for the 2016 NBA All-Star Game introductions in Toronto. Photo: 2016 Getty Images
September 15, 2015 Where: At the Serena Williams Signature Statement by HSN show during Spring 2016 Style360 in New York City. Photo: 2015 Getty... September 15, 2015 Where: At the Serena Williams Signature Statement by HSN show during Spring 2016 Style360 in New York City. Photo: 2015 Getty Images
June 8, 2015 Where: On stage at the Apple Worldwide Developers Conference in San Francisco. Photo: 2015 Getty Images
April 12, 2015 Where: Performing at the Coachella Valley Music and Arts Festival. Photo: 2015 Getty Images
July 16, 2014 Where: On stage at the 2014 ESPYS in Los Angeles. Photo: 2014 Getty Images
July 16, 2014 Where: Backstage at the 2014 ESPYS in Los Angeles. Photo: 2014 Getty Images
July 16, 2014 Where: On stage at the 2014 ESPYS in Los Angeles. Photo: 2014 Getty Images
July 16, 2014 Where: On stage at the 2014 ESPYS in Los Angeles. Photo: 2014 Getty Images
July 16, 2014 Where: Performing at the 2014 ESPYS in Los Angeles. Photo: 2014 Getty Images
June 12, 2014 Where: On stage for the Houston Appreciation Weekend. Photo: 2014 Getty Images
February 1, 2014 Where: At the Time Warner Cable Studios and Revolt Bring the Music Revolution event in New York City. Photo: 2014 Getty Images
October 28, 2013 Where: Performing a 'Would You Like a Tour?' Concert in New York City. Photo: 2013 Getty Images
October 27, 2013 Where: Performing a 'Would You Like a Tour?' Concert in New Jersey. Photo: 2013 Getty Images
September 21, 2013 Where: At the 2013 iHeartRadio Music Festival in Los Angeles. Photo: 2013 Getty Images
August 25, 2013 Where: At the 2013 MTV Video Music Awards in New York City. Photo: 2013 Getty Images
February 10, 2013 Where: At the 55th Annual Grammy Awards in Los Angeles. Photo: 2013 Getty Images
September 6, 2012 Where: At the 2012 MTV Video Awards in Los Angeles. Photo: 2012 Getty Images
February 3, 2012 Where: At ESPN The Magazine's 'NEXT' event in Indianapolis. Photo: 2012 Getty Images
January 29, 2012 Where: At the 2012 Tim Hortons NHL All-Star Game in Ottawa. Photo: 2012 Getty Images
January 21, 2012 Where: At the Bing presentation of Comedy with Aziz Ansari and a Drake Performance in Park City, Utah. Photo: 2012 Getty Images
December 31, 2011 Where: Performing on 'New Year's Eve 2012 With Carson Daly' in New York City. Photo: 2011 Getty Images
November 16, 2011 Where: At the Google and T-Mobile launch of Google Music in Los Angeles. Photo: 2011 Getty Images
August 26, 2011 Where: At the 11th Annual BMI Urban Awards in Los Angeles. Photo: 2011 Getty Images
June 26, 2011 Where: At the 2011 BET Awards in Los Angeles. Photo: 2011 Getty Images
June 19, 2011 Where: On stage with Justin Beiber and Selena Gomez at the 2011 MuchMusic Video Awards in Toronto. Photo: 2011 Getty Images
June 16, 2011 Where: At the Songwriters Hall of Fame 42nd Annual Induction and Awards in New York City. Photo: 2011 Getty Images
March 27, 2011 Where: At the 2011 Juno Awards in Toronto. Photo: 2011 Getty Images
February 13, 2011 Where: At the 53rd Annual Grammy Awards in Los Angeles. Photo: 2011 Getty Images
February 12, 2011 Where: At the Cash Money Records Annual Pre-Grammy Awards Party in Los Angeles. Photo: 2011 Getty Images
November 17, 2010 Where: At the 2010 GQ 'Men of the Year' Party in Los Angeles. Photo: 2010 AFP
October 5, 2010 Where: At the 'So Kodak' launch in New York City. Photo: 2010 Getty Images
September 12, 2010 Where: At the 2010 MTV Video Music Awards in Los Angeles. Photo: 2010 Getty Images
June 27, 2010 Where: Performing at the 2010 BET Awards in Los Angeles. Photo: 2010 Getty Images
June 27, 2010 Where: On stage at the 2010 BET Awards in Los Angeles. Photo: 2010 Getty Images
April 17, 2010 Where: At the 2010 Juno Awards Red Bull Party in St. John's, Canada. Photo: 2010 Getty Images
February 5, 2010 Where: At the Axe Lounge at Fontainebleau Miami Beach. Photo: 2010 Getty Images
February 5, 2010 Where: At Hotel 994 in Miami Beach. Photo: 2010 Getty Images
January 31, 2010 Where: In the press room at the 52nd Annual Grammy Awards in Los Angeles. Photo: 2010 Getty Images
January 31, 2010 Where: With his mother, Sandi Graham, at the 52nd Annual Grammy Awards in Los Angeles. Photo: 2010 Getty Images
December 2, 2009 Where: At the Grammy Nominations Concert Live! press room in Los Angeles. Photo: 2009 Getty Images
November 22, 2009 Where: At the 2009 American Music Awards in Los Angeles. Photo: 2009 Getty Images
June 28, 2009 Where: At the 2009 BET Awards in Los Angeles Photo: 2009 Getty Images
June 18, 2007 Where: With Jessie Williams and Michael Copon at the What Teens Want Party for Nikelodeon Network The N in New York City. Photo: 2... June 18, 2007 Where: With Jessie Williams and Michael Copon at the What Teens Want Party for Nikelodeon Network The N in New York City. Photo: 2007 Getty Images
1 / 53

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