Drake’s Best Courtside Outfits

Analyzing Drake's coolest courtside fashion throughout the years, everything from his Chrome Hearts basics and snakeskin Jordans to his OVO Dsquared sweater.

Drake's best courtside outfits
Complex Original

Image via Complex Original/Sylvia Hoang

Drake's best courtside outfits

One of the more overlooked tragedies brought on by the COVID-19 pandemic—after, you know, all the actually terrible stuff we’re still collectively wrapping our heads around—was that we had to endure a season and a half of classic Raptors basketball without their official ambassador sitting courtside. With our lone wayward Canadian team stranded down in Florida for the better part of two years, Drake had to watch games like the rest of us, from across the other side of the continent—which meant, even more tragically, that we all had to do without Drake’s big courtside fits.

The 6ix God is nothing if not an international style icon, and his choice of luxe ensembles as he cheers on the Raps have proven to be some of his most memorably stylish by far. In honour of Drake’s triumphant, long-awaited return to the Scotiabank Arena for the start of the 2021 basketball season—as well as the man’s 35th birthday on this very day (October 24)—we’ve rounded up the best of the best of Drake’s courtside fits.

OVO Dsquared2

Visvim Kerchief Down Jacket

Chrome Hearts Basics

.@Drake in “Snakeskin” Air Jordan 11’s last night courtside

📷 @ComplexSneakers pic.twitter.com/71Xxk7eHbv

— J23 iPhone App (@J23app) November 24, 2018

Drake says he gave his custom Kobe jacket from the All-Star Game to Steph Curry! https://t.co/qPpbydxrNy pic.twitter.com/YWFJxRt8fy

— theScore (@theScore) March 5, 2016

Dell Curry Finals Jersey

Drake's "Breaker High" hoodie has Canada freaking out 🌊https://t.co/pnp0CGLfOa pic.twitter.com/TZVwVLVv3F

— Complex Canada (@complexcanada) May 8, 2019

100 Miles Hoodie

Drake Courtside 1

When: 2019

Game 6 of the 2019 NBA Eastern Conference Finals was memorable for several reasons: the Raptors punching their ticket to the Finals, that Lowry smile, and this Tupac-inspired hoodie Drake wore at the game. An homage to Pac’s character Birdie in the 1994 basketball drama Above the Rim, the piece was custom-made for The Boy by Toronto-based brand 100 Miles, who actually made the original hoodie worn in the film by the rap legend. Drake asked for his to have “Kawhi Me a River” embroidered on the back in white letters, a tribute to then-Raptors star Kawhi Leonard. He rounded out the fit with a blue bandana and some “Ivory Snake” Nike Air Force 1s.

Gucci Jacket and Scarf

HOWLING pic.twitter.com/wGIjZPHR3e

— Justin Rowan (@Cavsanada) November 10, 2014

8:30pm in @ScotiabankArena pic.twitter.com/xiWs4Jnz5O

— Toronto Raptors (@Raptors) October 12, 2021

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