Key Takeaways
- With Iceman on the way, we examine the six signature items that define Drake’s style across his nearly 20-year run, framing him as a quietly influential dresser even if he’s not always in “best dressed rapper” debates.
- From OVO varsity jackets and Stone Island sweaters to Chrome Hearts cross patch jeans and NOCTA x Nike Glides, the piece shows how Drake’s wardrobe evolved from OVO in the blog era to global arena tours and high-end collabs.
- The story also nods to his accessories and merch moments—like the Nike Certified Lover Boy “Lipstick” hat and Pharrell’s chains—underscoring how Drake uses clothes and jewelry to project heartbreak, wealth, and competitive flexes.
For nearly 20 years, Drake has been one of hip-hop’s greatest commercial draws, filling out stadiums around the globe and battling the Beatles for Billboard accolades.
As much star power as he has had, Drake’s personal style has always been debated. While some of his actions have had a definite impact, like when he helped Stone Island surge stateside in the 2010s, he’s also largely left out of most “best dressed rapper” conversations. But make no mistake – Drake has achieved enormous success in apparel at the arena, boutique, and licensed levels.
As Iceman approaches, we wanted to take a look back at Drake’s style evolution, from OVO owls to Stone Island sweaters to NOCTA sneakers. These are the six pieces that define Drake’s style.
Hat: Nike Certified Lover Boy “Lipstick” Hat
Honorable Mentions: Camo Aaliyah Hat, Scarbarough Shooting Stars Cap
Half-moon ceasers, heart-shaped parts, and low fades have crowned Drake’s headtop much more famously than the signature caps that stamp, say, Jay-Z or Chance the Rapper. Nevertheless, his Heartbreak Drake persona received top-billing on the lipstick-smeared CLB cap.
Partnering with Nike on a line of non-NOCTA merch in 2020, the strapback hat nodded to Drake’s love of UK grime and its wardrobe, while making it his own with 6-God tagging and a ruby red kiss on the brim.
Top: Stone Island Sweater
Honorable Mentions: Hotline Bling Turtleneck, Jaden Smith & Doris Burke Longsleeve Tees, TOPSZN Johnny Manziel Tee
Around the time A$AP Nast was sending shots at Travis Scott for swagger jacking Stone Island, Drake was quietly making the Italian-born, UK favorite his own. He is the artist who was truly introducing a generation to the label in North America. Throughout his Roadman era in the 2010s, he stayed draped in full Stone Island both in the wild and on stage. The lengths of his love for Stone Island range from attending the 2017 Grammy Awards in a full set to sporting the badge at Wimbledon. He even immortalized his love for the brand with a diamond chain by Ben Baller.
The constant co-sign proved to be a beta test of sorts, as many eventual NOCTA offerings would borrow a similar blend of tactical utility upped by elevated elements and blunt branding.
Jacket: OVO Varsity Jacket
Honorable Mentions: Gruppo Vava V Jacket, Iceman Hooded Work Jacket, Bullethole Jacket from It's All a Blur Tour
At its height, October’s Very Own was in a class of its own. Beginning as a blog in 2009 before becoming a record label in 2012, the brand grew so quickly that a clothing line and flagship stores soon followed. By the mid-2010s, the all-seeing OVO owl sat firmly atop the Air Jordan collab hierarchy aesthetically, while being among the first to publicly platform future superstars like The Weeknd sonically.
Being down with The North was not historically cool stateside, but that changed in the mid 2010s when October’s Very Own became an apparel player with a flagship on La Brea Ave in Los Angeles and a satellite shop on Bond St. in New York City. The pinnacle piece was the varsity jacket created in collaboration with fellow Canadian brand Roots, infinitely rebranded through licensing partnerships, but worn most boldly when he attended Yeezy Season 1 in New York. Drake has rocked plenty of more vibrant, viral jackets since, but nothing defines his career quite like the signature piece from his own brand.
Pants: Chrome Hearts Cross Patch Jeans
Honorable Mentions: Baggy leather “trash bag” pants, Baggy Pleated Soccer Dad Pants
When Drake entered the rap game, he could rock fitted jeans 'cause his credit card was skinny. In the time since his arrival, he has amassed a bank account splitting at the seams and pants baggy enough to make Michael Jordan jealous.
His collection of Chrome Hearts cross patch jeans captures the current Drake: affluent enough to press the stunt button on any item, yet still set on the pulse of the youth’s taste, thanks in part to cohorts like Lil Yachty and Shai Gilgeous-Alexander. Being able to drop insanely exclusive Chrome Hearts cross patch jeans as a means to commemorate Certified Lover Boy in 2021 is a rich flex, indeed.
Shoes: NOCTA x Nike Glide
Honorable Mentions: OVO x Air Jordan 8 “Coach Cal,” OVO x Air Jordan 10, NOCTA x Nike Hot Step
Drake’s sneaker resume has flown a bit under the radar in comparison to some of his peers, but it’s one of the best. Since 2015, high-powered collaborations with Jordan and Nike have not only made his personal brand bigger but also shed light on his more intricate taste.
Though Charles Oakley-inspired Air Jordan 8 PEs and snakeskin Air Jordan 11s may be considered better sneakers, the Jason Kidd-referencing NOCTA Glides from his own sub-label draw from Drizzy’s ability to bend nostalgia in a manner that feels fresh, identifiable, and innovative. What’s more definitive than your own sneaker?
Accessory: Pharrell’s Chains
Honorable Mentions: Tupac Crown Ring, Previous Engagements Necklace
The Boy’s inheritance of Birdman’s “What Happened to That Boy” beef has made Drake more war-ready and aggressively petty than anyone ever imagined. Spending mansion money on Pharrell’s famous jewelry collection proved the last - for now - step in an ongoing battle with Pusha T.
Drake’s jewelry collection is one of the greatest in hip-hop history. Using his earnings to take the family jewels from Skateboard P and Tupac alike is only the tip of the iceberg. It’s a cold game for anyone occupying rap’s throne for over a decade, with few colder than the Iceman.
