sitting pretty /ˈsɪtɪŋ ˈpɹɪti/ adjective2 •(informal) Having a comfortable or certain supply of money or resources.Part of that memorandum of Mr. Hanshue's refers to directors sitting pretty in thinking they were all set for certain benefits. — 1934 •(informal) In a favorable situation, especially a situation in which one possesses an advantage."I was sitting pretty all the time, Derry." Al had laughed at the self-accusation in her eyes. "You can tell them all from me—I was sitting on the world." — 1919
