Drake’s songs are always certified bangers, whether you like to admit it or not. But his outfits? Straight flops, almost as regularly. Shining style moments for the For All The Dogs rapper are few and far between but in mid-November, Drake stepped out for dinner at Mamo in New York City and it looks like someone finally laid out some clothes for him before he left the house. 

Listen, when you’re as successful as Drake, it might be easy to think that it doesn’t matter what you wear but come on — it always matters.

And recently, Drake has been donning some of the most unflattering garments we’ve seen in a long time.

Let me present his painfully ’90s Fubu shirt and baggy jeans, complete with pink hair clips, between tour stops on his All A Blur tour as evidence.

We at HighSnob are clearly divided on these recent looks (ahem, Mr. I Love Those Horse Hoof Loewe Shoes) but they are a clear miss for me, Drake’s assumed target audience, in terms of dressing to impress.

There’s not anything even wrong with any of the singular items he dons per se. Maybe it’s the way he tucks shirts in or doesn’t, always choosing the wrong choice. Maybe it’s just a size issue, but for some reason, he always looks somewhat messy and not in a good way. Sorry, bruv. 

But this past weekend, something was in the air, as it looks like Drake had a little help with his outfit. The lovelorn singer is always looking for a mate, right, so maybe he’s on the prowl to impress a certain someone? There is no factual or even rumored basis for this hypothesis, but something is going on! Drake finally nailed a billowing, perfectly layered, autumn-in-New-York silhouette.

Drake truly looked sharp, as my grandmother would say as she adjusted my grandfather’s collar under his suit before a family wedding.

Clad in a pair of grey slacks, a black turtleneck sweater with a silver chain, a tweed coat, and some brown Special Occassion shoes that must have been collecting dust in his closet, he is clearly going for Meg Ryan-level sophistication.

With his hair tied back in braids and his glasses, Drake looked rather dapper, as again, only an Italian grandmother could put it. Sort of like he was going to church, maybe, but a clear step up from dressing like he was on the Degrassi soundstage in 2001, in 2023. 

It does make sense that Drizzy wanted to clean up a little for his night out. Mamo is reportedly his go-to spot in Manhattan, as the restaurant regularly closes down for him to share a bite with his mom —sharp! — or what Page Six conservatively described as a “bevy of women.” 

In July 2023, for example, the outlet reported that the Canadian rapper pulled up with 20 women after a show at Madison Square Garden, and it wasn’t the first time that had happened. Drake doesn’t need to pull out many stops to impress the women of his dreams, but it looks like something is clearly in the works. When else does the Certified Lover Boy pull out a turtleneck sweater and chain? 

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