Definition of "penniless"

A dollar and a quarter seems a small sum, but if you are absolutely penniless it might as well be a thousand.

1889, Horatio Alger, chapter 10, in Driven From Home

This time was most dreadful for Lilian. Thrown on her own resources and almost penniless, she maintained herself and paid the rent of a wretched room near the hospital by working as a charwoman, sempstress, anything. In a moment she had dropped to the level of a casual labourer.

1918, W[illiam] B[abington] Maxwell, chapter XVII, in The Mirror and the Lamp, Indianapolis, Ind.: The Bobbs-Merrill Company