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1.
A tongue-in-cheek ironic remark given to a person or group who says or does something overly offensive or classless.

Originated in the 2004 film "Anchorman" from Will Ferrell's sign-off: "Stay classy, San Diego". In the film, he meant it literally.
"The Haitian earthquake was caused by Haiti making a deal with the devil."- Pat Robertson

"Stay classy, Pat Robertson."
by RySenkari January 14, 2010
 
2.
1. Staying cool and sophistcated.
2. A sarcastic way of saying "Dude, that was so unclassy, so better luck next time. Don't do that." Said after you said something that was uncool or after you fail.
1. "Stay classy everybody!"

2. James: "Hey umm... wait, what's your name again?"
Girlfriend: "*Gasp!* I'm sooo offended!! Good-bye!"
Nick: "Stay classy James!"

Grant: "Wait, the test was today? Ohh... I didn't study."
Nick: "Stay classy."
by carrots823 April 20, 2011