this refers to a guy that appears to be attractive with a hat on but once the hat is removed you realize he is in fact balding and/or not attractive hatless, like the country singer Kenny Chesney.
I went home with that hot older guy, Matt, but when he took his hat off I could see that he was suffering from acute Chesney Syndrome.
by abigail normal November 3, 2012
Term used to describe men on online dating sites who only post pictures of themselves wearing a hat, sunglasses, or both to hide the fact that they are unattractive, cross-eyed or bald.
"This guy's cute but I totally think he has Kenny Chesney Syndrome, he has a hat on in every picture"
by bustedbeatbox August 2, 2011