There’s no debate, Drake is still the most popular rapper in the world, despite his very public defeat to Kendrick Lamar in the rap battle of the century.
As a result, everything “The Boy” does is under a microscope, even his fits. Just recently, hip-hop fans had a lot to say about his recent Instagram post, claiming that he was taking some shots at Lamar in the caption.
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Ignoring the post, the 6-God put together his best outfit in a while. But in the past, the Toronto rapper’s fashion sense has always been under fire. He’s always had a knack for keeping up with trends, but hasn’t necessarily put them together the best and has moments where he misses the mark entirely.
With that in mind, let’s look back at some of his highest and lowest fashion moments over the years.
2024
Analyze the caption as much as you like, this is a fly-ass fit. Giving that old-money vibe while taking in his son’s soccer game.
2024
This is another good fit from The Boy. These Loewe boots have been a favorite of his and he’s always paired them together with a solid baggy outfit. In this fit, he went with a clean oversized coat.
2023
Drake has always loved his jerseys. In this fit, he opted for a vintage LeBron James jersey from his time at St. Vincent St. Mary. It’s nothing anything special, but it’s not terrible.
2022
We may be too broke to even understand what he’s doing here. But the two Teddy Bears on the coat are a unique piece, you have to give him that.
2021
This is a smooth look from The Boy. No notes.
2020
Air Force ones, Black skinny jeans, and a blue jean jacket. This is an outfit you could find any teenager wearing at the time. Either way, it’s one of his many mediocre fits.
2019
The thumbnail for this video isn’t a lie. He’s literally wearing an outfit that’s worth $1 million. It’s a dapper look.
2018
I like this fit simply for the sweatshirt he’s wearing. He wore multiple variations of college sweatshirts during his “Aubrey & the Three Migos Tour” in 2018.
2017
Drake was in his Stone Island era in 2017, and he rocked some dope jumpsuits from the Italian luxury brand., including this one from the 2017 Billboard Awards.
2017
I like when artists step out of their comfort zone and pull it off. Drake looks clean here. Love that burgundy leather jacket.
2016
Drake loves his Timbs. But this has to be one of the worst fits he’s put together with them. Any other jacket but the one he has would’ve made this better.
2016
This shirt alone makes this fit an L. It’s not the fact that it’s pink, it’s that it’s way too long. Make sure to check your measurements before putting on a piece like this Drake. d
2015
Simple streetwear outfit that was pretty normal for the time. It’s even cooler that he’s wearing a pair of OVO Jordan 8s and a varsity jacket from his brand.
2015
The OVO Jordan 12s are dope. But this vest/jacket he’s wearing is questionable at best.
2014
Although it was a part of his costume for a bit he was doing at the 2014 ESPYS, it was still atrociously bad.
2014
Timbs and a varsity jacket have been a go-to for the 6-God during his time in the spotlight.
2014
Gotta be honest, this looks like the first time Draek has ever worn Jordans in his life. This is an example of him poorly trying to keep up with the trends.
2013
All Black is never a bad idea and Drake pulled it off well here.
2013
Another fit that isn’t trash, but not great. The only thing that makes this outfit somewhat noticeable is the photo of Jaden Smith on his shirt from when he witnessed Miley Cyrus’ ridiculous performance at the 2013 VMAs.
2012
V-neck. Who made these damn things fashionable? Either way, it looks like the manager of a Miami beach club.
2011
I know this is from 2011, but this is even bad even for the time. I don’t ever remember a time when yellow dress shoes were in vogue.
2010
Like many on this list, this outfit didn’t make Drake stand out from other rappers (his music did that), but you can’t fault him for this look. It isn’t awful.
2009
This fit is all over the place. The Comme des GARÇONS cardigan is a nice piece, but the henley shirt underneath is questionable. In the end, it’s pretty mediocre.
2007
I guess Drake was trying his best to give off that preppy look. (It doesn’t work).
2005
Although this comes from his days as an actor on “Degrassi,” this outfit is still a dud. He’s dressed more like a teacher rather than a student.
Straight From 
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