- (idiomatic) Having a comfortable or certain supply of money or resources.
1934, Investigation of Air Mail and Ocean Mail Contracts, United States Congress Senate Special Committee to Investigate Air and Ocean Mail Contracts, page 2804:
- Part of that memorandum of Mr. Hanshue's refers to directors sitting pretty in thinking they were all set for certain benefits.
1973 July 20, “People in the News”, in Time:
- Lauren Hutton, 28, was sitting pretty. The omnipresent model had just signed a two-year, $200,000 contract.
2014, Michelle Lee, The Unexpected Package, page 90:
- I asked her if she realized Michael could be killed in Iraq and she had laughed and said it wouldn't matter as long as she had the baby she would be sitting pretty with his death benefits.
- (idiomatic) In a favorable situation, especially a situation in which one possesses an advantage.
1919, Donn Byrne, The Strangers' Banquet, page 351:
- "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."
1922, Rex Ellingwood Beach, chapter 24, in Flowing Gold:
- I'm in control. I'm sitting pretty. They can't unseat me, and I warn them not to try.
2010, Donald O'Donovan, The Sugarhouse: A Novell:
- We were both sitting pretty back then, back in the 20th Century.
- (having a comfortable or certain supply of money): living on easy street