Drake Always Plays It Cool With Fashion: His Best Looks

Drake always impresses Us with his raps, but his wardrobe is just as noteworthy.

The hip-hop star — who released his eighth studio album, For the Dogs, in October 2023 and has amassed five Grammys, 29 Billboard Awards and countless other accolades — tends to play it cool when it comes to his personal style. His staples include high-end denim and luxury outerwear. He’s known to rock puffer coats and shearling jackets by major fashion houses and coveted collaborations, including the beloved Supreme x Louis Vuitton collection.

Drake is also particular about his footwear, only donning the coolest sneakers and sometimes even boots. Accessories are also important to the Canada native.

In December 2022, the “God’s Plan” crooner revealed that he had a diamond necklace made of rings he never used to get engaged. Jewelry designer Alex Moss unveiled the piece, titled “Previous Engagements,” via an Instagram video. In the clip, Moss showed off the sparkler, which features 42 engagement rings made of 351.38 carats of diamonds.

Keep scrolling to see Drake’s best outfits of all time:

September 2023 Drake Style Evolution

Credit: Prince Williams/WireImage

September 2023

Drake wore a black letterman jacket with a graphic T-shirt and baggy black jeans at a party in Atlanta. He topped the look off with white platform shoes.

December 2022 Drake Style Evolution

Credit: Prince Williams/Wireimage

December 2022

He bundled up in a black leather jacket and accessorized with his “Previous Engagements” sparkler at a Lil Baby concert in Atlanta.

November 2022 Drake Style Evolution\

November 2022

Drake had all eyes on him when he attended an NBA game in a cream fur coat adorned with two attached teddy bears by Jean-Charles de Castelbajac.

October 2021 Drake Style Evolution

October 2021

The “Slime You Out” rapper made a statement in a red fur coat and camo pants at a Toronto Raptors game in Canada.

May 2021 Drake Style Evolution

May 2021

He rocked a custom three-piece suit by Tom Ford at the Billboard Music Awards in Los Angeles.

September 2019 Drake Style Evolution

September 2019

Drake wore a charcoal gray Tom Ford suit at the Top Boy premiere in London.

August 2019 Drake Style Evolution

August 2019

He was all smiles in a shirt adorned with Bob Marley’s face at a party with David Grutman and French Montana in Miami.

June 2019 Drake Style Evolution

June 2019

He teamed a black cashmere sweater with a brown Tom Ford blazer at the premiere of Euphoria in Los Angeles.

May 2019 Drake Style Evolution

May 2019

Drake donned a plum bespoke suit by Brioni at the Billboard Music Awards.

April 2019 Drake Style Evolution

April 2019

The hitmaker rocked a blue bandana-inspired WMV Visvim jacket at a Toronto Raptors game in Canada.

August 2018 Drake Style Evolution

August 2018

He performed in a bullet-proof vest during his Aubrey & The Three Amigos Tour stop in Chicago.

July 2018 Drake Style Evolution

July 2018

Drake rocked a bright orange crewneck by I Can’t Decide Yet while out and about in Los Angeles.

April 2018 Drake Style Evolution

April 2018

He was seen in a glossy Gucci jacket after a night of clubbing in London.

September 2017 Drake Style Evolution

September 2017

June 2017 Drake Style Evolution

June 2017

He channeled his inner James Bond in a white and black look by Tom Ford at the NBA Awards in New York City.

May 2017 Drake Style Evolution

May 2017

Drake wore a flannel shirt and jeans at an event at the Sugar Factory in Las Vegas.

November 2016 Drake Style Evolution

November 2016

He styled an unbuttoned shirt underneath a black blazer and matching pants at the American Music Awards.

September 2016 Drake Style Evolution

September 2016

He wore a snake-adorned jacket at a nightclub in Las Vegas.

September 2015 Drake Style Evolution

September 2015

Drake sported a velvet hoodie while sitting next to Anna Wintour at the Serena Williams Signature Statement by HSN show in New York City.

July 2014 Drake Style Evolution

July 2014

The rapper looked sharp in an ivory blazer at the ESPYs.

December 2013 Drake Style Evolution

December 2013

He performed in a blue ombre tank at the Palace of Auburn Hills in Michigan.

November 2013 Drake Style Evolution

November 2013

He nailed the monochrome trend in an all-gray ensemble while performing in Sacramento.

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