sitting pretty

• (Received Pronunciation) IPA^(key): /ˈsɪtɪŋ ˈpɹɪti/
• (General American) IPA^(key): /ˈsɪtɪŋ ˈpɹɪti/, /ˈsɪɾɪŋ ˈpɹɪɾi/

• Audio (General Australian):

  (file)

• Hyphenation: sit‧ting pret‧ty

sitting pretty (not comparable)

1. (idiomatic, informal) Having a comfortable or certain supply of money or resources.

   Synonym: living on easy street

   • 1934, Investigation of Air Mail and Ocean Mail Contracts: Hearings before a Special Committee on Investigation of Air Mail and Ocean Mail Contracts, United States Senate, Seventy-third Congress, Second Session, pursuant to S. Res. 349 (72d Congress), a Resolution Creating a Special Committee of the Senate to Investigate Air Mail and Ocean Mail Contracts, Washington, D.C.: United States Government Printing Office, →OCLC, 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, archived from the original on 14 December 2008:

     Lauren Hutton, 28, was sitting pretty. The omnipresent model had just signed a two-year, $200,000 contract.

   • 2014 June 11, Michelle Lee, The Unexpected Package, : Trafford Publishing, →ISBN, 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.

   • 2021 January 30, Tanya Sweeney, “The Irish architect who became the ‘megamansion king’ of LA”, in The Irish Times‎:

     Calvin Klein is reportedly sitting pretty in another of McClean's dazzling $25 million Hollywood Hills creations.

   • 2024 September 16, Mehera Bonner, “Wondering What Dan Levy Is Making for Hosting the 2024 Emmys? Here's a Deep Dive on His Net Worth!”, in Cosmopolitan‎:

     Either way, the multi-hyphenate [Dan Levy] signed a 8-figure deal with Netflix in 2021 (per Variety) so he's sitting pretty either way!

2. (idiomatic, informal) In a favorable situation, especially a situation in which one possesses an advantage.
   • 1919, Donn Byrne, “chapter XXVI”, in The Strangers' Banquet, New York, N.Y., London: Harper & Brothers Publishers, →OCLC, 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 Beach, “chapter XXIV”, in Flowing Gold, New York, N.Y.: Grosset & Dunlap Publishers, by arrangement with Harper & Brothers, →OCLC, page 290:

     That's not a threat, sir, for they have played fair with me, and I sha'n't sacrifice a penny of their money—unless they force me to do so. But—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 Golden Age: From the Novel Orgasmo”, in The Sugarhouse: A Novella: Plus Four Novel Excerpts from Orgasmo; Night Train; Confessions of a Bedbug Hauler; Tarantula Woman, : Open Books:

     We were both sitting pretty back then, back in the 20th Century.

• “sitting pretty”, in Cambridge English Dictionary, Cambridge, Cambridgeshire: Cambridge University Press, 1999–present.
• “sitting pretty” (US) / “sitting pretty” (UK) in Macmillan English Dictionary.
• “be sitting pretty” in Longman Dictionary of Contemporary English, Longman.
• “sitting pretty”, in Collins English Dictionary.