Green’s Dictionary of Slang

(US black) a large-brimmed, oversized hat in 1930s–40s style.

1971		R. Woodley Dealer 3: Applejacks – dusters – tilted forward over their foreheads.
1999		‘Badman Brown’ Smudge Ch. 5: From head to toe, he was clean. Clean and bright. Mostly, he liked sporting his new white leather jacket with his new white Applejack hat. The pimp walk he acquired to go along with his new attire, fit him tastefully well also.
2002		Soul Patrol 🌐 I turned my head a little bit & looked on the stage & there was this real skinny ‘white boy’, dressed like a ‘funkateer’(he had on an ‘applejack hat’ , ‘nik-nik’ shirt, platform shoes, etc) playing the chit out of the great Hendrix song ‘Voodoo Chille’.