Drake is one of the most successful and influential rappers of his generation, but he is also known for his style and confidence on stage. The Canadian artist has evolved his fashion sense over the years, from his early days of wearing throwback sweaters and New York streetwear to his current preference for high-end denim, luxury outerwear, and statement pieces. Drake’s onstage fashion reflects his personality, his mood, and his music, as he mixes different brands, colors, and styles to create his own unique look.

2018 Halloween Party

When: 2018

Yes, this is actually a Fabolous Halloween costume. No, that doesn’t make the nostalgic fit any less fire. Drake rolled up to this 2000s-themed party in 2018 giving a nod to someone he refers to as one of his biggest inspirations in rap. It was the exact fit worn by Loso in the “Trade it All Pt. 2” music video. The throwback Minneanapolis Lakers Kobe Bryant jersey, baggy white undershirt, Los Angeles Dodgers fitted cap, and a baby blue bandana over top. Nice. *Fabolous voice*

Empire Lounge (Atlanta)

Image via Getty/Prince Williams

When: 2018

Hey yo! Drake was oozing with machismo when he stepped out in this vintage Razor Ramon T-shirt. Surely to be appreciated by wrestling fans, Ramon (Scott Hall) was among one of the most popular professional wrestlers throughout the ‘90s with stints in the WWF and WCW to boast about. The bold yellow and black all-over graphic T-shirt couldn’t have come from any other decade. It’s one of the more valuabe vintage wrestling shirts, too. The Adidas track pants and white Adidas Climacools on feet also represent a very short-lived stint repping the Three Stripes back in 2018.

2017 Billboard Music Awards

Image via Getty/Allen Berezovsky

When: 2017

Fact: Drake makes great music. Fact: Drake loves Stone Island. This picture accurately confirms both things. Drizzy attended the 2017 Billboard Music Awards in the all-white Stoney fit. Here he can be seen flexing with this record-setting 13 awards. Make sure to take note of the super crisp white Air Force 1s on foot as well. Shoutout to this super cozy award show fit.

“Top Boy” U.K. Premiere

Image via Getty/Karwai Tang

When: 2019

Sure, Drake has some fashion misses under his belt. We all do. But whenever he decided to step out in a suit it’s usually a hit. His appearance at the U.K. premier for Netflix’s Top Boy in September of 2019 was no different. A classic black suit (likely some custom Brioni or Tom Ford, but cannot confirm), grey turtleneck underneath, and a diamond necklace to accessorize. *chef’s kiss*

2019 NBA Eastern Conference Semifinals

Image via Getty/Vaughn Ridley

When: 2019

Drizzy doesn’t mess around when it comes to the Scotiabank Arena courtside fits. For the 2019 Eastern Conference Semifinals, he pulled out a serious statement piece, a blue paisley Visvim Kerchief down jacket from the cult-favorite Japanese brands Fall/Winter 2012 collection. He kept the rest of the pieces subtle—a white T-shirt, light washed denim, white Nike Air Force 1, and a single diamond necklace for good measure.

2019 NBA Eastern Conference Finals

Image via Getty/Ron Turenne/NBAE

When: 2019

Drake had an impressive run of courtside outfits throughout the Toronto Raptors 2019 NBA Playoff run. One of the standouts is this nod to Tupac he wore during Game Six of the Eastern Conference Finals, a custom “100 Miles” hoodie inspired by Pac’s character Birdie from 1994’s “Above the Rim.” While he didn’t tie a bandana around his head like the late rap legend, he stayed on brand with one tied around his neck. Drake provided his own twist on the hoodie by embroidering “Kawhi Me a River” on the back in bold white letters, a tribute to superstar Kawhi Leonard. “Ivory Snake” Nike Air Force 1s on feet are just an added bonus.

2019 NBA Finals

Image via Getty/Garrett Ellwood/NBAE

When: 2019

Two things we have been able to establish thus far, Drake loves the Toronto Raptors and he loves to be petty with his outfits. This fit from Game One of the 2019 NBA Finals between the Toronto Raptors and Golden State Warriors checks both boxes. Here he can be seen celebrating courtside in a throwback Dell Curry Raptors jersey. Dell is the father of Warriors point guard, Stephen Curry. The jersey choice set Twitter on fire that night. Dell and wife Sonya were even impressed at the rapper’s choice. No “Drake Curse” on display here either. The Raptors won the game 118-109. Drake is playing chess with his fits. We’re all just playing checkers.

Los Angeles

Image via Getty/Hollywood To You/Star Max

When: 2019

This is one of Drake’s outfits that had the internet searching for a way to acquire it for themselves back in July 2018. Perhaps inspired by his Scorpion cut “Finesse,” he stepped out in a bright orange University of Tennessee crewneck with the letters meticulously carved out to read “Finesse” instead. The piece was designed by lowkey brand icantdecideyet who surely appreciated the buzz brought forth by the monumental cosign. As he is known to do, Drake kept it cozy with a pair of black nylon track pants and matching Nike Air Max Plus sneakers to complete the casual Los Angeles look.

Nike 2020 ForumImage via Getty

When: 2020

When Nike brought its 2020 Forum runway show to New York Fashion Week, Drake was in attendance and coordinated a matching outfit with Virgil Abloh. Drake and Virgil  both wore camouflage jackets from Arc’teryx LEAF line. The jackets they wore were the Alpha Jacket LT Gen 2 Multicam and is only sold to law enforcement or military personnel. So yes, I guess you can say Drake laid down the law with this crazy Arc’ fit paired with black jeans and Air Maxes.

Chrome Hearts and The North Face

Image via Getty

When: 2020

Drake loves Chrome Hearts. So much that, we received a Certified Lover Boy x Chrome Hearts merch months before the album even dropped. Here we see how Drake reps the pricey Los Angeles-based label, wearing a pair of the brand’s famous jeans customized with leather cross patches. This outfit features a good mix of high and low. A humble 700-Fill North Face Nuptse, all-white Nike Air Force 1s, a heather grey hoodie, and a Louis Vuitton satchel completes this great Drake fit.

“Checks Over Stripes”

Image via BG020/Bauer-Griffin/GC Images / Getty

When: 2021

Drake stays loyal to Nike. His own label, OVO, has released numerous sneaker collaborations with them. And Nike even collaborated with Drake to produce his own techwear-inspired clothing line dubbed Nocta. Along with Nike producing official Certified Lover Boy merch, it’s very clear that Drake is deeply aligned with the brand. And if the music video for “Laugh Now Cry Later” didn’t make Drake’s love for Nike clear enough for you, this fit showing Drake wearing Nike from head to toe definitely will.

(N)umber Nine Courtside

Cole Burston / Getty Images

When: 2022

It’s crazy how Drake really pulls his best pieces out when watching the Toronto Raptors play. When he took his son Adonis to watch them face the Chicago Bulls in February of 2022, he came decked out in a crazy archival jacket rom the Japanese label (N)umber Nine. The piece Drake wore is known as the “Touch Me I’m Sick” Heart Patchwork Coat and is from (N)umber Nine’s AW03 collection. Two decades later it clearly holds up and can fetch as much as $6,000 on the resale market today.

$1.9 Million on The Neck, $270,000 on The Wrist

Cole Burston / Getty Images

When: 2022

Here’s an example of Drizzy letting one piece do all the talking. This fit Drake wore to a Toronto Raptors game in March of 2022 is honestly very calm. He’s really just wearing a simple gray T-shirt, with black pants and sneakers. But really, it’s clear that Drake did all that so that we pay attentition to the jewelery piece on his neck. Yes, that’s the $1.9 million chain designed by Frank Ocean’s jewelery line Homer. The 127.5-carat diamond necklace is crafted out of 18-karat white gold pavé-linked orbs, boast 9,226 lab-grown VVS diamonds, and was only previously worn by Frank Ocean himself at the 2021 Met Gala. To top it all off, Drake also wore a matching Homer bracelet that cost $271,500 alone.

Brothers in Mink

Prince Williams / Getty Images

When: 2022

Lil Yachty and Drake’s relationship is one of the most endearing friendships within hip-hop today. So it’s not surprising that these two coordinated fur outfits together for 21 Savage’s Freaknik performance in October of 2022.

The Chill Canadian Fit in New York City

Gotham / GC Images

When: 2023

When Drake stopped by New York City during his “It’s All a Blur” tour in 2023, he stepped out in some very laid back outfits. This one he wore while strolling around Manhattan’s Upper East Side is a perfect example. Drake walked around New York with just some simple gray sweatpants, a vintage mesh Molson “Canadian” baseball jersey, and some platform-soled, shearling-lined Loewe boots. Honestly, shearling boots is a wild footwear choice to put on during one of the hottest summers to date in New York City. But if we’ve learned anything about celebs, it’s that there’re impervious to body heat. And Drizzy still nailed the rolled-out-of-bed look with grace.

When: 2023

When it comes to insane celeb jewelery purchases, 2023 was a crazy year for Drake. He was really collecting jewelry previously owned by other rappers like Dragonballs. While the old school BAPE varsity jacket he wore is cool, the old Pharrell pieces he wore in his “Jumbotron Sh*t Poppin” video were truly the highlight of this memorable look. Drake rocked almost $3 million worth of P’s old jewelry for the video. undefined

When: 2023

When it comes to insane celeb jewelery purchases, 2023 was a crazy year for Drake. He was really collecting jewelry previously owned by other rappers like Dragonballs. While the old school BAPE varsity jacket he wore is cool, the old Pharrell pieces he wore in his “Jumbotron Sh*t Poppin” video were truly the highlight of this memorable look. Drake rocked almost $3 million worth of P’s old jewelry for the video. undefined