The photo has no date but can be dated by Sinatra's time with Reprise Records. The photo is circa 1960s.
Billboard page 39 November 26, 1966-copy of photo.
This work is in the public domain in the United States because it was
published in the United States between 1929 and 1977, inclusive, without a
copyright notice. For further explanation, see
Commons:Hirtle chart as well as a
detailed definition of "publication" for public art. Note that it may still be copyrighted in jurisdictions that do not apply the
rule of the shorter term for US works (depending on the date of the author's death), such as Canada (50
p.m.a.), Mainland China (50 p.m.a., not Hong Kong or Macao), Germany (70 p.m.a.), Mexico (100 p.m.a.), Switzerland (70 p.m.a.), and other countries with individual treaties.
Photo has been cropped and minor flaws fixed. Previous upload was to establish source, help with timeframe, and show there are no copyright marks on it.