Oh, these were fun descriptions and discussions.
Since it has been evolving and different folks use it different ways, I echo rachy and some others who include an emotional component or something that pulls someone else in , or is intended to, or to get attention in either a positive or negative way. So I would
not typically use it for just a mishmash outfit, for example, or someone just having a bad day, though I might, or hear otgrst, referring to self as hot mess to make light, or fun, but not REALLY.

What a great thread - hats off to La Ped!
(For me the connotation is definitely a total mess.)

As it is used in the south, it refers to a big mess, or a total mess. Nothing to do with hot as a compliment!

Thanks for asking the question, Angie! I have never used it because like you I didn't understand it exactly. Very interesting explanations everyone, thank you!

My maternal grandmother used this term all of the time. I always assumed it was from the 1920's or 30's.

I've always associated it with drug addiction, TBH. Like referring in a derogatory way to someone (male or female) who is out of their mind, unaware of their surroundings, disheveled, but also "easy" sexually. In my mind, it's associated with the "addict fashion"/Heroin chic that became fashionable in the 90's. Think, Courtney Love.