Jack Harlow’s Hats, Ranked

Jack Harlow has suddenly become a man of many hats.

The rapper-turned-R&B/neo-soul experimentalist decided to not only switch up his sound for his most recent project Monica, but he also switched up the wardrobe to a more late ’90s/early ’00s Earth tone aesthetic, and decided to get kinky with the headgear as if he recently came across the underrated cult comedy Fear of a Black Hat. He spoke on his whole hat philosophy when he made an appearance on the New York Times’ Popcast.

“It all started with the music, and whatever the music sounded like, I just decorate around it appropriately,” he told the outlet. “And of course, there are certain things that point to another time and era, but you know the Kangol is a symbol of something, I think.” He then said that he threw the hat on, looked in the mirror and right then and there decided that it fit the vibe of the music he was making while also admitting that he’s trolling a bit in order to start a conversation. And in that regard, I would say, “Mission accomplished.”

A friend and I have a joke we always go to when we see somebody wearing a funny hat or a hat that we don’t like. The joke in question is essentially a random line from an inconsequential scene in Quentin Tarantino’s Kill Bill, Vol. 2 where Budd (played by the late Michael Madsen) strolls into his s–tty strip club job late and gets confronted by his boss Larry Gomez (played by the late Larry Bishop) for always wearing a “s—t-kicker” cowboy hat. Larry then looks at Budd and says, “The hat, that f–kin’ hat” with a look of disgust and disappointment.

Now, Jack Harlow’s hats don’t fit into the “shit-kicker” category, but I have found myself mumbling that same very line when he pops out with another one of these absurd hats. And you, too, might find yourself doing the same as you go through some of these looks. The hat he decided to wear at this year’s Kentucky Derby inspired this list and it’s like a mix of the Sleepytime Tea nightcap with a graduation cap. Unfortunately, we couldn’t include it in this ranking due to legal purposes, so I’ll just link back to it so you can see for yourself.

In the meantime, check out our ranking of Jack Harlow’s hats below.