Drake’s Worst and Best Fashion Moments Over the Years

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.

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.

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.

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.

This is a smooth look from The Boy. No notes.

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.

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.

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.

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.

I like when artists step out of their comfort zone and pull it off. Drake looks clean here. Love that burgundy leather jacket.

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.

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 

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.

The OVO Jordan 12s are dope. But this vest/jacket he’s wearing is questionable at best.

Although it was a part of his costume for a bit he was doing at the 2014 ESPYS, it was still atrociously bad.  

Timbs and a varsity jacket have been a go-to for the 6-God during his time in the spotlight.

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.

All Black is never a bad idea and Drake pulled it off well here.

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.

V-neck. Who made these damn things fashionable? Either way, it looks like the manager of a Miami beach club.

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.

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.

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.

I guess Drake was trying his best to give off that preppy look. (It doesn’t work). 

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.