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:

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.

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.

Credit: Cole Burston/Getty Images

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.

Credit: Cole Burston/Getty Images

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.

Credit: Rich Fury/Getty Images

May 2021

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

Credit: Mike Marsland/WireImage

September 2019

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

Credit: John Parra/Getty Images

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.

Credit: Gregg DeGuire/FilmMagic

June 2019

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

Credit: Jeff Kravitz/FilmMagic

May 2019

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

Credit: Vaughn Ridley/Getty Images

April 2019

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

Credit: Prince Williams/Wireimage)

August 2018

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

Credit: Hollywood To You/Star Max/GC Images

July 2018

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

Credit: Ricky Vigil M/GC Images

April 2018

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

Credit: Taylor Hill/FilmMagic

September 2017

Credit: Taylor Hill/FilmMagic

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.

Credit: Steven Lawton/Getty Images

May 2017

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

Credit: Michael Tran/FilmMagic

November 2016

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

Credit: Denise Truscello/WireImage

September 2016

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

Credit: Grant Lamos IV/Getty Images

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.

Credit: Kevin Mazur/WireImage

July 2014

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

Credit: Scott Legato/Getty Images

December 2013

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

Credit: Tim Mosenfelder/Getty Images

November 2013

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

 

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