The Kentucky rapper keeps wearing various hats, so we ranked them from worst to best.

5/7/2026

Jack Harlow attends the 2026 Met Gala celebrating "Costume Art" at the Metropolitan Museum of Art on May 04, 2026 in New York City. John Shearer/WireImage

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.…