The Big Green Tractor star, his wife Brittany Kerr, and a group of pals appeared to dress up as gangsters for their Halloween festivities, but Aldean seemingly took his costume one step further by donning a wig of dreadlocks and darkening his skin with cosmetics.
The image, which first appeared on NashvilleGab.com, attracted criticism online, with Twitter users blasting Aldean for showing "bad judgement" with the "upsetting" garb, while others questioned if it really was Aldean under the sunglasses and gold jewellery.
His representative, Tyne Parrish, has since confirmed the authenticity of the picture, revealing Aldean was "dressed as rapper Lil Wayne for Halloween", but the publicist didn't share any further explanation and offered up no apology for what many have deemed offensive.
The rap star has yet to comment on the news.
Aldean is no stranger to scandal - he was caught cheating on his first wife and high school sweetheart Jessica Ussery in 2012, when snaps of the singer kissing Kerr during a drunken night out appeared online.
Aldean previously blamed poor judgement for his infidelity, which occurred as he struggled with problems in his marriage.
"I think the biggest thing is, you know, obviously there was things going on in my marriage at the time where it just wasn't really happy," he told U.S. newswoman Robin Roberts. "And you go out and you kind of let your guard down a little bit and things happen, and unfortunately... it's tough."
Aldean claimed the media scrutiny which followed only made it more difficult for him to fix his marriage, adding, "When you have to deal with all that stuff in public, I mean, it's hard to - it's hard enough to deal with it in private."
He eventually filed for divorce in 2013, and went public with his new relationship with former American Idol contestant Kerr last year (14). They wed in Mexico in March (15).