Originally used to describe a man of independent wealth who could pursue whichever interests he so chose while the average man was busy working. The term was used by pimps to describe the lifestyle they had embraced.
Momma - "Boy, how you get all this money? I know you ain't workin for it."
Son - "Momma, you know I'm a man of leisure."
Momma - "Is that what they're callin it these days. You just a pimp and a mack. You ain't foolin no one, boy!"
Son - "Momma, you know I'm a man of leisure."
Momma - "Is that what they're callin it these days. You just a pimp and a mack. You ain't foolin no one, boy!"
by Suvonoge August 14, 2008

by Chananime November 3, 2012

Being born into a wealthy New England family Kate Hepburn was the kind of woman of leisure who, these days, might be found on wealthymen.
by Help Us Put a Stop to Collar Pop May 19, 2006

Anne: Hey Elisa, what did you say your job was?
Elisa: Oh I'm a lady of leisure! I just do whatever and see where life takes me.
Anne: So you're basically being pretentious about being unemployed?
Elisa: Am not! I was using it ironically!
Elisa: Oh I'm a lady of leisure! I just do whatever and see where life takes me.
Anne: So you're basically being pretentious about being unemployed?
Elisa: Am not! I was using it ironically!
by mrperson123 April 30, 2019

Jumping in mid-air over (usually) a body of water and striking a leisurely pose as if, say, laying on the beach reading a book.
by bbcplease March 15, 2014

Cyrus styles hissself a gentleman of leisure but he nothin' but a low-down, raggedy-ass pimp, if you axe me.
by Tunmy AuGratin February 28, 2006

My buddy Bob is a leisure activist. He hasn't ever had a job and he lives off of his annual dividend check from his parent's company. I think he just got back from 6 months in Thailand.
by p mammen November 22, 2009
